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Chapter Text

Chapter One | A Mutual Alliance

Against her better judgment, Jenny Humphrey finds herself standing outside of 1136 Fifth Avenue. It’s the last place she wants to be, after all, her high school bully resides here, not to mention some of her worst memories have taken place here. 

But after last night’s worrying phone call with Vanessa, she can’t shake the feeling that something bad is going to happen to Serena, and not just the typical Upper East Side display of humiliation, but something rather precarious. Jenny may have had a few ups and downs with Serena in the past – and that’s putting it lightly – but she can’t in good conscience let anything happen to the ‘It Girl’ while knowing she can do something to prevent it from happening.

So, after a morning of deliberating, she decides to share her concerns with a third party, someone close to Serena with an experience of manipulation and scheming and with the authority to take full control of the situation.

Unfortunately for Jenny, only one person fits the bill, and it just so happens to be the person in all of New York who despises her the most.

With a sigh, she drags her feet towards the entrance of the penthouse. The doorman recognizes her and ushers her inside the private elevator. As the doors slide shut, she attempts to squelch the rising bubble of panic inside of her chest. She’s reluctant to admit it, but Jenny feels rather nervous to see Blair Waldorf. 

In an effort to distract herself, her eyes drift over to the elevator mirror and she finds herself gazing at her own reflection. She looks tired; her eyes are puffy, her makeup woefully lacking, and her hair is flatter than usual. As she had taken the first train from Hudson early that morning, she had no time to make an effort with her appearance, but if she wants to be taken seriously by Blair, she has to look presentable. 

Very carefully she removes the elastic band she keeps on her wrist and twists her hair into a messy bun. She has no time to do much else and decides it will have to do. 

The elevator door chimes open, and she walks out. Dorota is sitting in one of the foyer chairs, reading a book. At the sound of Jenny’s footsteps, she jumps up, startled, and drops her book. 

“Little Humphrey,” she breathes, caught off guard.

Jenny nods her head in greeting. “Dorota. Is Blair around? I really need to speak with her.”

“Miss Blair is not available,” she responds, fumbling with her French Maid hat. 

“Please, Dorota. It’s important.”

“If Miss Blair is to find you here, things will turn ugly. You must leave before she sees you.”

Jenny doesn’t move. Instead, she says, “I promise I wouldn’t have come here if it wasn’t important.”

“If it’s about Mr. Chuck, you should go,” Dorota says, shaking her head. “There is no point. Miss Blair will not listen to anything you have to say.”

“It’s not about Chuck,” Jenny says insistently. “It’s about Serena. I think she’s in trouble. That Juliet girl is up to something, I just know it.”

The maid appears thoughtful for a moment. Jenny wonders, not for the first time, why Dorota remains loyal to the Waldorf's, especially given the way they treat her. Dorota’s protectiveness over the Waldorf Heir makes no particular sense. Sure, Blair doesn't treat her nearly as bad as her mother Eleanor does, but there were definitely times where she made Dorota’s life hell. 

She feels the heavy weight of Dorota’s stare and fidgets uncomfortably. The maid continues to scrutinize her closely, as if trying to discern the truth from her form. After a short moment, Dorota finally says, “Wait here,” and disappears among the spiral stairs.

 She returns shortly, a disgruntled Blair by her side.

The fashion heiress takes one look at Jenny and folds her arms across her chest. “I thought I made it clear that you’re not welcome here,” she says with a nasty glare.

“Crystal,” Jenny says, taking a mimosa glass from the discarded breakfast tray left on the foyer table. “Your incessant reminders couldn’t have made it any clearer.”

Blair huffs in annoyance. “Chuck sent you here, didn’t he? Of course, he did! He’s still trying to get back at me because I got rid of Little Miss Sunshine.”

Jenny files Blair’s outburst away for later; as curious as she is about what happened to Eva, she knows better than to ask. After all, she doesn’t want to get involved in whatever war Chuck and Blair are currently in.

“I haven’t spoken to Chuck since I left for Hudson,” Jenny replies pointedly, “so no, he didn’t send me here.”

“Then pray tell Little J, why are you here?”

“Not for your personality, that’s for sure,” Jenny mumbles under her breath. As Blair’s glare intensifies, she says, “Look, I know we don’t like each other …”

It’s Blair’s turn to mutter, “That’s an understatement.”

“...but I’ve been hearing things, particularly about Juliet, and she’s bad news.”

“And that concerns me how?” Blair asks, inspecting her fingernails in boredom.  

“Because she’s trying to sabotage Serena.”

“Like how you were trying to sabotage her last year?”

Jenny clutches the mimosa glass harder. “That’s different,” she says defensively. “I may have tried to ruin Serena’s relationship with Nate, but I never tried to hurt her in any way.”

“Because trying to steal someone's boyfriend isn’t at all hurtful,” Blair says in a mocking tone. “OK, I’ve entertained this conversation long enough, I think it’s time you leave. I’ll be taking this.” 

She grabs the glass out of Jenny’s hand and turns away. “Don’t let the door hit your derrière on the way out.”

“Wait,” Jenny says hurriedly. Her mind races with thoughts as she formulates what to say next. She needs to grab Blair’s attention now if she wants to be taken seriously.

For a moment, she almost considers telling Blair about the tips that have been sent to Gossip Girl about Juliet. According to sources, Juliet wasn’t actually rich and was living off her wealthy cousin’s money. The crème de la crème, however, was the tip about her older brother Ben; the former teacher currently in jail for grooming a minor.

The words are on the tip of her tongue, but she stops herself in time. She can’t disclose this information, not without giving away her identity as Gossip Girl.

Instead, Jenny chooses her next words carefully. “I spoke to Vanessa last night. She told me all about Juliet’s plans to ruin Serena. They even have a whole itinerary drawn out for next week’s masquerade. I know you, Blair, and as much as you hate me, you’re going to want to hear this.”

At the mention of the masquerade, Blair pauses in her steps. Without turning around, she says, “I’m listening.”

“Well, their main goal that night is to ruin Serena’s relationship with both Dan and Nate. Obviously, Juliet wants Nate all to herself and Vanessa wants my brother,” Jenny explains. “Their plan is to gaslight the boys into thinking Serena chose each of them and then make them think she’s playing with their feelings.”

“And how do you know this?” Blair asks, turning to look at her with suspicion.

“They’ve approached me to help them with this.”

Blair tries to hide her interest. “I see. And are you going to help them?”

“No,” she says without hesitation. “I told them I wouldn’t do it. I’m past the point of scheming and I only want to move forward with my life.”

Blair rolls her eyes at this but remains silent. 

“With Nate and Dan out of the way, that’s one layer of Serena’s defense gone,” Jenny continues. “Next would have to be her relationship with you and Chuck, then Lily and Eric.”

“Puh-lease,” Blair says, waving her hand dismissively. “Like they can turn me against Serena. Our bond of sisterhood is unbreakable.”

The conviction of her statement makes Jenny want to laugh. Blair and Serena turn on each other as often as the weather changes and Blair’s ability to forget this simply shows how out of touch the upper east side could be. From friendship one minute to hostility the next, the ingenuity of it all makes her feel a bit better that she’s no longer a part of it.

“Right,” she drawls. “But my point remains. Juliet is clearly scheming to get Serena alone. Don’t you find that suspicious?”

“I may find it a little suspicious,” Blair admits, “but that doesn’t necessarily mean what you’re saying is true. In fact, for all I know this could be a complete waste of my time. You have a reputation for being a liar. Why should I believe you for even a second?”

Jenny sighs, stepping closer. “That’s fair. You don’t have to believe me—hell, I wouldn’t believe me if I were you. But this time, I am very much telling the truth,” she insists. “I’ve already lost my reputation, my place at Constance, my family’s respect. Even my own father can’t look at me the same way. I have nothing left to lose here.”

Blair hesitates, her sharp gaze narrowing as she weighs Jenny’s words.

Jenny presses on. “And let’s not forget how much I’m risking just by being here. I could’ve gone to Chuck, but I came to you. You’re better at scheming than he is, and we both know it’ll piss him off if he finds out.”

She sees the flicker in Blair’s eyes—the undeniable glint of pride—and knows she’s struck a chord. When Blair’s lips curl into a faint, satisfied smirk, Jenny is certain she’s won her over.

“Flattery gets you nowhere, Little J,” Blair replies smoothly. “But fine. Seeing as I’m feeling extra generous today, I suppose I can co-conspire with you.”

With that, Blair gestures for Jenny to follow her into the drawing room before disappearing upstairs to retrieve her infamous notebook. Left alone in the opulent room, Jenny lets her mind drift, replaying the chain of events that brought her back to Blair Waldorf’s doorstep…

It all started when she received a call from her stepbrother on the weekend of their parent’s first wedding anniversary. She had already informed her dad that she couldn’t attend their small party as she was ‘studying’ for a test, when in reality, Jenny was honoring the terms of her banishment set by one Blair Waldorf. That day, she was sitting in her room, sketching some designs into her drawing pad, when her phone rang.

With a quick glance at the caller ID, she answered on the second ring. “Hey Eric. How are things?” she asked softly.

“Jenny, things aren’t looking too good,” Eric said. His voice sounded more nervous than usual, and he spoke really fast. “I think you need to come down here.”

“I can't,” Jenny said quickly. “Not without getting caught in the crossfires of Chuck and Blair. It’s too risky for me to be seen in Manhattan. Blair has minions everywhere .”

“I understand where you’re coming from,” Eric said, “but there are bigger things at play. Not sure if you’ve been reading all the tips sent into Gossip Girl, but Blair and Chuck just had a ceasefire.”

Jenny leaned closer into the phone. “What does that mean exactly?”

She heard Eric’s sigh come from the other end of the phone and braced herself for his next words. 

“It means that there won’t be a war, not anymore. But your presence is definitely enough to set them off again.”

“Wait, so why do you want me to come if it’s enough to risk another war?”

Subconsciously, she acknowledged how ridiculous the entire conversation sounded, with the mention of metaphorical wars and ceasefires, but then again, this was the Upper East Side, which always had the flair for the dramatic.

“Well, it’s Dan. He’s pissed at Chuck and Blair for not allowing you to return for the anniversary. Chuck was down to help initially, but after the peace treaty, he’s refusing to go against Blair,” Eric said quietly. “Now, Dan’s made a plan to get back at them and I’m ninety-five percent sure that it’s going to go horribly wrong.”

“What kind of plan?” she asked, as she continued to sketch absentmindedly.

“Um, well, he kind of just stole their entire treaty - which was meant to go into a remote storage facility for security – and is planning to use the information listed to humiliate Blair at her own birthday party.”

The lead of Jenny’s pencil snapped. “He what ?”

 That didn’t sound like her big brother, who was the moral compass of the family. Amongst all her shitty decisions and reckless behavior, he was the good kid, who always listened to his parents and bailed his little sister out of unwanted trouble. Sure, he had a few shortcomings of his own (his horrible taste in girlfriends, for one), but he wouldn’t go this far for petty revenge. There was absolutely no way she was going to let him risk his own reputation amongst the Upper East Side for her. She’d rather deal with Chuck and Blair any day than let Dan get pulled into their twisted games.

So, she did what any other good sister would and booked the first train to Manhattan. After explaining to her mom that she wanted to surprise her dad for his anniversary celebration, she packed her bag and made her way to the city.

However, upon arriving at an empty penthouse, she realized that everyone was already at Blair’s party and wondered if it was too late to drag her brother away from his scheming. She knew she couldn’t exactly waltz into the party – not only was she not invited, but she was certain that she was listed on the ‘no entry’ page – so she waited outside Blair’s penthouse, hoping one of her brothers would make an appearance.

With no luck, she decided to call Eric and asked him to meet her outside.

“Hey, Jenny,” he said, closing the door behind him and pulling her into a hug. “You really came.”

“Of course,” she said, giving his shoulders a squeeze before pulling away. “Where’s Dan?”

Eric adopted a painful expression. “He’s still inside somewhere. I told him to call the whole thing off, but he said it’s too late.”

“What do you mean it’s too late?”

“Don’t shoot the messenger,” he said, holding his hands up. “I tried to get him to stop but he wasn’t listening.”

Jenny opened her mouth to say something but paused when the sound of mass laughter echoed from within the apartment. Both she and Eric turned to look at the door as realization hit them.

“He’s done it,” Eric said in horror,” he must’ve already played the video.”

She wanted to ask what video he was referring to but knew this wasn’t the time nor the place. They had to get Dan out of there before any suspicion fell onto him. At her insistence, Eric went back into the penthouse and dragged a reluctant Dan out of the party.

“Things were just getting interesting,” Dan protested. 

Jenny wagged a finger in his direction. “Not now. Let’s just head home before things get worse.”

Once they arrived back at the Van Der Woodsen/Humphrey residence, the trio set about making paper flowers for their parents. Dan explained how Blair had thought Chuck had set the whole thing up and had shredded the treaty into pieces in front of the whole party. 

“If Eric didn’t grab me when he did, I would have told them it was all my doing,” Dan said, stapling a paper rose together.

Given the amount of Gossip Girl blasts they had received that night, it was official. The war was well and truly back on.

Later that night, Lily and Rufus returned to the penthouse, and the family – sans Serena – celebrated the union of the Van Der Woodsen’s and Humphrey’s. Jenny had to admit, it was lovely being home, even for a short while.

The next morning, she went back to Hudson, and was preparing for school the following day. She didn’t necessarily lie about having a test to study for. She had an algebra test the next day and so spent the rest of her afternoon solving complex equations. When she had enough and was ready to throw her textbook at a wall, she received another phone call. This time, from Vanessa.

And when she answered the call, Vanessa had an interesting proposition lined up, regarding one Serena Van Der Woodsen. Instead of accepting outright, Jenny told her friend that she would consider it. But after reading a few tips sent into the Gossip Girl inbox, and doing some research of her own, she felt sick to her stomach.

There was absolutely no way she was going to help the sister of that predator with her silly vendetta. 

So, she spent the rest of her evening formulating a plan, one that involved the help of her nemesis and her minions. After booking a train ticket to Manhattan early the next morning, Jenny went to bed, her mind racing with all sorts of ideas and schemes. 

The algebra test would just have to wait. Manhattan needed her.  

Jenny is brought back into the present when Blair sets a heavy book onto the table with a thump! She scoffs when she reads the title. 

“The Art of War? Are you reading that in hopes to outsmart Chuck or are you going to batter him with it?” she asks, teasingly.

“Hmmph.” Blair takes a seat opposite her. “What I plan to do with Chuck is none of your business. We’re here to discuss the Juliet and Vanessa situation, if I’m not mistaken.”

“You’re not,” Jenny sighs. “I was trying to make a joke.”

“Well, don’t. We’re not friends.” Blair is quick to remind her. “Merely acquaintances. Allies, if you will. We have enemies in common that require taking down.”

Jenny scoffs again. “This isn’t a battlefield, Blair. We’re not soldiers. All we need to do is put a stop to their plans, not ‘take them down’, as you so put it.”

Blair chooses to ignore her comment. Instead, she summons Dorota and requests the maid to bring them coffee and pastries.

“I’ll have a vanilla latte, no foam,” she says, before turning to look at Jenny. “And you?”

When Jenny doesn’t respond, she adds, “It doesn’t take a genius to figure out you’ve skipped breakfast today. Your disheveled state says it all.”

Jenny blinks at her thoughtfulness. “Uh, black coffee is fine, thanks.”

Blair rolls her eyes at the choice and shoos Dorota away. 

“Now then, where were we?”

While Dorota brings them their treats, Jenny recounts her entire conversation with Vanessa. After careful consideration, she decides to tell Blair at least one truth about Juliet, a tidbit that she learned after an anonymous tip had been submitted to Gossip Girl regarding the girl’s real social status and wealth.

“Should have known she was Brooklyn trash,” Blair comments, taking a sip of her latte. “I mean Nate was all over her, and he has a thing for strays.”

In a rare display of self-restraint, Jenny lets the comment slide and contains her urge to throttle the brunette. “While your classism isn’t appreciated, I don’t think that’s the sole issue here,” she says instead.

“Evidently.” Blair raises a perfectly arched brow. “How do you know about all of this?”

“I did my research,” Jenny says off-handedly, hoping she wouldn’t press further. “People in Brooklyn talk. I asked around and found out a helluva lot.”

“Hmph. Not bad, Little J,” Blair says, smiling, when she notices the blonde flinch.

“Stop calling me that,” she says.

Blair’s smile only broadens. “So aside from being poor and from Brooklyn, what else could Juliet be hiding? And why does she hate Serena so much? I mean, I get that S is so much prettier, smarter, and everything that Juliet wishes she could be, but surely that isn’t reason enough to destroy her life? Unless…it’s the Nate thing. But then again, even he isn’t worth this much effort. We have to be missing something here.”

Jenny takes a bite of her pastry, relieved that Blair seems to be taking this as seriously as she wanted her to. She knows she made the right decision by coming to her for help. All she has to do at this point is guide the brunette in the right direction, and the rest will fall into place.

Blair is a powerhouse, and once she finds out about Juliet’s true motives, Jenny is sure that all hell will break loose.

“I have an idea, but we’ll have to get it done before the Ballet tonight,” Blair continues. She glances at her watch and her demeanor shifts into a serious one. “I’m going to call someone I trust to help us.”

Jenny raises an eyebrow, but before she can voice her curiosity, Blair cuts her off. “And before you ask, no, it’s not Chuck. He’s the last person on Earth I would ask for help,” she snaps, disappearing into another room to make the call.

When she returns, she places her sleek Blackberry on the table with finality. “He’ll be here in five minutes.”

They finish their coffee, the air thick with unspoken questions. Jenny’s mind races, wondering who Blair had called. But she doesn’t have to wonder for long.

The elevator chimes again, and the sound of approaching footsteps fills the room. Jenny turns in her seat, her curiosity transforming into shock as she meets the piercing blue eyes of Nate Archibald.

For a moment, time seems to hang still. Nate’s gaze flicks between Jenny and Blair before he does a visible double-take. “So, clearly I’ve missed a chapter here. Does anyone want to bring me up to speed?”

Blair’s lips curl into a knowing smirk. “You’ve read the ‘Art of War’, Nate. Surely you remember the phrase: ‘Keep your friends close, your enemies even closer’.”

Chapter Text

Chapter Two | The Golden Boy, The Queen Bee, and The Gothic Barbie

It’s been a while since Jenny has seen Nate, and she can’t say she isn’t feeling awkward. She gives him a nervous smile as he takes the seat directly across from her and next to Blair. He doesn’t return her smile and simply stares back at her, suspicion evident in his eyes.

She doesn’t blame him. She did just sabotage his relationship mere months ago, and as they say in the upper east side, you can’t forgive without forgetting.

“Um,” she clears her throat, “what Blair means to say is, we’ve decided to put our differences aside for a bigger cause.”

“Oh, I’m sure you have.” His voice drips with sarcasm. “What ‘cause’ could possibly unite the two of you?”

Blair decides to run interference and waves a hand as if dismissing his concerns. “Trust us,” she says. “We know what we’re doing. Unlike the peace treaty I made with Chuck, this is a temporary truce that will no longer bind once the situation has been resolved.”

“I made no such agreements,” Jenny protests, but is ignored by Blair.

“The fact of the matter is, someone is trying to sabotage Serena, and we need to put a stop to it.”

Nate jerks his head in Jenny’s direction. “Are you referring to her?”

“Surprisingly, no. I’m actually referring to your latest fling,” Blair says as Jenny frowns at the accusation. She knows she made a mistake – okay, a massive one – but surely, he would let it go by now.

Nate doesn’t seem to share her sentiment. 

“So why do you need Jenny’s help? Wouldn’t it be counterproductive to ask the girl who tried sabotaging Serena before, to stop the new girl from sabotaging Serena now?”

“Ouch,” Jenny mutters.

Blair rolls her eyes. “That’s exactly why we need her help. She’s the only person who is just as skilled as me when it comes to manipulation. And no, Georgina doesn’t count because she’s bat-shit crazy.”

“And Chuck?” Nate asks. “Couldn’t you conspire with him instead?”

“You’re joking, right. After his display of humiliation at my birthday party, you really think I’d willingly talk to that Basshole? I’d choose Gothic Barbie over him any day.”

“Again, I’m right here,” Jenny interjects, but is once again ignored.

“Look, I know that it seemed as if he deliberately ruined your birthday party, but he swears it had nothing to do with him. And I believe him. Maybe you two should talk. I can arrange another round of negotiations for a peace treaty with a better outcome this time,” Nate says, adopting a diplomatic tone. “Don’t you think it’s time the two of you bury the hatchet?”

“The idea of being in the same room as him is insulting,” Blair scoffs, “and don’t try to change the subject. The only thing I’ll be burying is Juliet’s reputation once I’m through with her.” 

Nate sighs. “Okay, fine,” he says, leaning back in defeat. “But how do you know that Juliet is trying to sabotage Serena? She seems like a perfectly nice girl to me.”

Try as she may, Jenny can’t contain the snicker that escapes her mouth. She can feel the intensity of Nate’s gaze as she says, “That’s because you trust anyone. And that’s coming from me, a person who has actually betrayed your trust on multiple occasions.”

Blair almost looks proud of her. “Look, Archibald, since you won’t listen to her, you’ll just have to take my word for it. You know how credible my sources are,” she says.

“Alright, I’ll hear you out before making any final judgements,” Nate says with another painful sigh, his blue eyes still trained on Jenny. The blonde straightens her back, feeling self-conscious with all the attention.

“Wise decision,” Blair says as she checks the time on her custom designed wristwatch. “Right, we have exactly four hours until the ballet tonight. Little J, bring Golden Boy up to speed, will you.”

Rolling her eyes at the order, Jenny begins to fill Nate in, using the same rehearsed tidbits of information she fed Blair with earlier. Nate continues to watch her closely and visibly frowns when she mentions her phone call with Vanessa.

She pauses to ask if he’s okay.

“I don’t know,” he answers as his frown deepens. “It just doesn’t sound like something Vanessa or Juliet would do.”

Jenny grits her teeth but remains quiet. It’s obvious to her that Nate thinks Vanessa and Juliet are above the scheming and manipulation of the upper east side, a courtesy he’s never once extended to Jenny herself. Even though Vanessa has betrayed him time and time again, he always forgives her, but still can’t find it in him to forgive Jenny no matter how much she apologizes. 

A wave of resentment washes over her and she’s ready to give him a piece of her mind when Blair, once again, beats her to it.

“Are you kidding me?” Blair huffs indignantly. “You’re acting as if they’ve painted the stars and hung the moon. Newsflash, they didn’t.”

“Look, all I’m saying is that this doesn’t sound like anything they’d do. Doesn’t mean I don’t believe you both,” he says, running a hand through his hair. “I just don’t understand why they’d do all of this to turn Dan and I against Serena.”

“Well, that’s the part we’re stuck on too,” Blair says. “She clearly has a grudge against Serena, we just need to figure out what it is and why.”

“There has to be more to her story than we think,” Jenny says, shifting in her seat. Of course, she already knows the real reason behind Juliet’s vendetta but can’t disclose this without revealing her identity. She’ll just have to point them in the right direction and convince Blair that it was her idea.

“Agreed. We’ll have to do a lot more digging before we have anything concrete,” Blair says, before turning her head to look at Nate. “This is why I called you. We need you to distract Juliet for at least an hour so that we can look through her apartment for any clues.”

“What?” Nate exclaims. “First you tell me all about how evil she is, and now you want me to spend some quality time with her so that you can break into her apartment?”

Blair nods. “And we’ll need to get it done before the Ballet tonight. I’m in the mood to do an exposé in front of the entire Columbia Faculty.”

Nate’s expression resembles that of a lost puppy. “But how am I supposed to keep her distracted for an hour?” he asks. “Not to mention, breaking and entering is a felony!”

“Use your wiles,” Blair says dismissively, “and don’t worry, I don’t plan on any one of us getting caught.”

“I still don’t know why you wanted me to come with you. My family doesn’t even know that I’m in Manhattan. They all think I'm at school. I’ll have to return to Hudson before the evening ends,” Jenny tells Blair as they’re sitting inside a taxi across from Juliet’s apartment.

It’s been over ten minutes since they’ve arrived and they’re still waiting for Nate’s signal that the coast is clear.

“Well, for starters, you don’t actually expect me to dig through her second-class apartment, do you?” Blair says with a scoff. “I’m used to penthouses, not doghouses.”

“Just because she doesn’t live in the upper east side doesn’t mean her place is ‘second-class’. And people who live in Brooklyn aren’t animals.”

“They might as well be.”

Jenny spots Juliet stepping out of her apartment to leave and grabs Blair by the arm. Together, they crouch in their seats so as to not be seen.

“Look, I know we don’t like each other. Some may even say we despise each other. But I’ve always respected you. Can’t you at least show me the same courtesy?” she says, her voice tinged with frustration.

Blair retracts her arm and whispers harshly, “Respect is something that is earned. You’ve slept with my boyfriend. I think that speaks volumes of your character.”

“And I regret it,” she whispers back. “You think I don’t feel ashamed? Because I do. I was drunk and lonely, and Chuck was the only person there for me that night and I wasn’t thinking straight –”

Blair holds up her hand. “Save it,” she hisses. “I don’t want to hear it. We’re not here for a tête-à-tête. We have more important matters to attend to.”

Just as Jenny is about to respond, Blair’s phone chimes with a text from Nate.

“He says the coast is clear. Let’s go.”

They exit the taxi and head towards Juliet’s apartment. Jenny fishes out a hair pin and successfully picks the locks of the apartment. She notices Blair watching her with fascination and ushers the brunette inside before anyone can see them.

Blair opens her purse and produces a pair of gloves. At Jenny’s raised brows, she scoffs, “What? Like you actually expect me to touch anything? This place is crawling with an array of different germs for all we know.” She gives the apartment a once over and shudders dramatically.

“I didn’t realize you were such a clean freak,” Jenny remarks as she starts routing through Juliet’s shelves. 

“I’m not a clean freak,” Blair insists. “I'm allergic to second-hand items, which, judging by the location, the apartment is full of."

Jenny scoffs. “Sure, because that’s a perfectly normal allergy to have,” she says, her voice laced with sarcasm.

Ignoring her, Blair slips on her gloves and begins to inspect the living room shelves. Jenny decides to leave her to it and makes her way to the bedroom. Everyone knows that’s where the secrets really lie.

Jenny flicks on the overhead lamp as she steps into Juliet’s bedroom, her heart beating a little faster than she’ll ever admit to Blair. It’s not like this is her first covert mission—far from it, given her secret life as Gossip Girl—but it’s one thing to know everything from a distance and another to be right here, physically snooping through someone’s apartment.

She scans the neat room with a practiced eye. For someone who’s allegedly strapped for cash, Juliet certainly keeps her space pristine. Too pristine. Jenny suspects that means Juliet is paranoid about leaving evidence lying around—or just very good at hiding it.

Out in the living room, Blair’s exasperated heels click across the floor. Jenny hears a muffled groan, likely prompted by a “second-class” piece of furniture. She can’t help rolling her eyes.

Focus, she tells herself, taking a quick breath. I need Blair to see exactly what Juliet’s hiding… without realizing I already know.

Jenny opens the bedside table drawers, sifting through a half-filled notebook, lip gloss, and a random old receipt. Nothing scandalous. She briefly wonders if Juliet keeps paper trails somewhere else or if she’s entirely digital—something Jenny already suspects. She’s read enough Gossip Girl tips and done enough behind-the-scenes digging to know Juliet’s the type who archives her ammo electronically.

“Anything interesting in there?” Blair’s voice carries from the other room.

“Just your typical trifles,” Jenny calls back, letting her frustration seep through. “No sign of sabotage or blackmail stashes yet.”

Truthfully, Jenny’s itching to suggest they check for a laptop—she knows from her Gossip Girl posts that Juliet keeps most of her evidence digital. But she doesn’t want to be too obvious. She’s playing the part of reluctant ally here, not omniscient spy.

Jenny moves toward the closet, glances over the neat rows of shirts, then flips through them aimlessly. Nothing here. Instead, she hears Blair let out a triumphant, “Aha!” from the living room. Good—Blair must’ve stumbled on the device.

“Jenny! Come here. Now,” Blair hisses.

Perfect.

Jenny forces a curious frown onto her face before hurrying out. She finds Blair crouched behind a scuffed coffee table, Juliet’s laptop open and glowing. Jenny notices how Blair’s eyes flash with that familiar “I just found gossip gold” excitement, and it’s all she can do not to smirk.

“I can’t believe it was just lying here,” Blair says, tapping her manicure against the keyboard. She glances up at Jenny. “Juliet’s either careless or supremely arrogant.”

Jenny shrugs, feigning innocence. “So, what is it?” She leans in, carefully orchestrating her body language so she looks hesitant and curious, not like someone who’s already seen these files in Gossip Girl’s inbox.

Onscreen is a grainy photo of Serena—blonde hair lit by city lights—entangled in a kiss with Colin Forrester. Jenny knew about this tryst well before now, courtesy of anonymous tips clogging her server, but she makes a show of surprise, brow furrowing as she inhales sharply.

“Oh my God,” she breathes, letting her eyes linger on Colin’s face. “That’s… definitely Serena. Is that a professor? From Columbia?”

Blair’s lips twist into a victorious scowl. “Yes, and if I had to guess, it’s from outside his apartment or near some fancy gala. Either way, it spells scandal if the wrong people see it.” She clucks her tongue. “She’s always playing with fire.”

Jenny pretends to scrutinize the screen, though her thoughts are already racing. She knows exactly how explosive this photo could be: it could potentially get Serena expelled—or worse, subject her to social ruin. On the other hand, it would draw a ton of traffic to Gossip Girl. Still, Jenny doesn’t want her step-sister (and sometimes rival) to suffer that badly. She can’t quite shake the guilt that she’s known about this all along.

“So this is what Juliet’s been keeping under wraps,” Jenny says, shaking her head. “Not good. She could leak it at any time.”

“She probably plans to.” Blair clicks around some of the folders, eyes skimming file names. “She labeled the picture ‘Expose_Serena.jpg.’ Subtle as a chainsaw. It’s obviously blackmail material.”

Jenny tries not to flinch. The fact that Juliet saved it in such an obvious way is comedic—though typical of the less-experienced saboteurs. “We can’t let her get away with this. Especially not tonight at the ballet,” she says, carefully prompting Blair. “She could email it to the entire Columbia faculty mid-performance.”

“Exactly.” Blair snaps the laptop shut with a flourish, pressing it to her side. “We can’t risk letting her hold onto this. We take the laptop.”

Jenny feigns alarm. “Juliet will definitely notice if her laptop’s gone. That’ll blow our entire plan.”

“Then do you have a better idea, Little J?” Blair demands, arching a brow.

Suppressing an eye roll, Jenny forces a composed sigh. “Yes. We copy the file onto a flash drive, then wipe it from her system. She won’t know what’s missing until it’s too late.”

Blair gives a reluctant nod. “Make it quick before I contract a disease from these plebeian surroundings.”

Classic Blair.

Jenny carefully reopens the laptop and slides a flash drive from her purse. She’s hyper-aware that she has to look like she’s done this once or twice, but not enough to make Blair suspicious. After all, the last thing she needs is for Blair to realize how computer-savvy she truly is—or that she’s been archiving Manhattan secrets for ages.

Blair paces the room while Jenny clicks, drumming her fingers against the edge of a chipped countertop. Jenny navigates Juliet’s folders with ease, quietly transferring “Expose_Serena.jpg” onto her flash drive. If only you knew how many times I’ve done this behind a screen, she thinks, biting her lip to hide a knowing grin.

“Done,” Jenny whispers, pressing ‘Delete’ and emptying the Recycle Bin. It’s not foolproof—someone with enough tech skills could restore it—but Juliet doesn’t strike her as a digital whiz. “Let’s hope Juliet isn’t savvy enough to run a recovery program.”

“We’ll cross that bridge if we come to it,” Blair says. She slings her purse over her shoulder and motions imperiously toward the door. “Now, let’s get out of here before Nate’s luck runs out.”

Jenny sets the laptop back exactly where Blair found it. “Agreed. In and out—like we were never here.”

They slip into the hallway, shutting the door behind them as quietly as possible. Jenny’s heart thuds in her chest, a mix of excitement and anxiety swirling in her stomach. So far, so good. Not only did they secure the evidence, but Blair still has no clue Jenny already knew about the photo.

Blair exhales a dramatic breath, looking oddly triumphant. “I need to sanitize my hands. That was so… dirty.”

Jenny can’t help a smirk tugging at her lips. “I’m pretty sure Juliet’s apartment won’t give you the plague, Blair.”

Blair narrows her eyes. “I’m taking zero chances. My minions aren’t around to douse me in hand sanitizer, so I’ll have to do it myself.”

A small laugh escapes Jenny—something she never thought she’d do in Blair’s presence. “What now?” she asks, tucking the flash drive safely into her bag. “We have the evidence, but Juliet has plenty of other moves, I’m sure.”

Blair lifts her chin, steel in her gaze. “I’m counting on that. Tonight, we’ll sabotage her sabotage. And when Juliet’s forced into the open, we’ll destroy her. No one threatens Serena on my watch.”

Jenny nods, thoughts already swirling with the next steps. She’s got more than enough insider knowledge to feed Blair the right leads without getting caught in her own web. But one crisis at a time.

“Then let’s hope Nate’s bought us enough time.” Jenny sets off down the hall, Blair’s heels clacking close behind. “We still have to meet him before the ballet.”

“And I need to come up with the perfect exposé,” Blair mutters, half to herself, half to Jenny. “If all goes well, Juliet Sharp will regret ever setting foot in Manhattan.”

If all goes well, no one will discover I’ve known everything from the start, Jenny thinks, hugging her purse tighter. She glances at Blair, a wary alliance flickering between them. “On that note, let’s make sure tonight is one Juliet will never forget.”

They disappear into the elevator just as footsteps echo from the stairwell—Juliet returning early, perhaps. But the doors close in time, and Jenny forces herself to breathe. For all the secrecy and tension, she can’t deny the surge of adrenaline coursing through her.

She was Gossip Girl, after all—and this is what she does best.

Jenny lowers herself into the worn, vinyl seat of the late-afternoon train bound for Hudson. She releases a slow breath, the hum of the engine beneath her feet a comforting white noise after the whirlwind day. She glances at her phone—it’s past six. If she’s lucky, no one in Hudson will notice she’s been gone. Her mom might be too caught up in her newfound artistic bliss to wonder why she’s back so late.

Just keep your head down, Humphrey, she tells herself. No more drama for today.

But the universe clearly has other plans. Her phone buzzes—four, five, six times in a row.

Here we go.

For a split second, she simply stares at the screen. She contemplates ignoring it—maybe she deserves a break from the backstabbing and scandal. Yet the pull of her old life is too strong. Sighing, she unlocks her phone.

The Gossip Girl inbox has exploded, as it always does whenever there’s an event on the Upper East Side. Tips pour in from nameless sources claiming to have the latest scandal: Chuck spotted leaving a hotel at 3 a.m.; Serena rumored to be flunking classes; Blair apparently orchestrating a sabotage of her own. Jenny feels the familiar rush—equal parts adrenaline and dread—rise in her chest.

She bites her lip, recalling all the times she would have posted every salacious rumor without question. When you’re Gossip Girl, she thinks, nothing’s off-limits. Except, now it feels different. She’s seen the damage one well-timed tip can do. She’s been the victim of it herself, and she’s caused it for others.

But old habits die hard. Her thumb hovers over the first unread tip: Spotted: Chuck Bass making side deals with an investor at The Empire bar. Where’s Eva now?

In the past, Jenny would’ve posted that in a heartbeat—piling onto Chuck’s misfortunes without a second thought. A small pang of conscience twists in her gut. She can’t deny some petty part of her would enjoy seeing Chuck squirm, especially after the events that had caused her public exile from Manhattan. But she recalls the wreckage from her last scheme: how easily a snippet of gossip could ruin livelihoods—or worse, reputations people worked their whole lives to build.

Her hand slides to the ‘Delete’ button. “No,” she whispers under her breath. “I’m better than this.”

She scans the next tip: Word on the street is Serena’s been spotted playing games with two guys at once. Could be trouble in paradise?

“Typical,” she mutters. She’s already aware of the complicated Dan/Nate/Serena triangle. And as if Serena needs more trouble right now. Tension squeezes Jenny’s chest when she remembers the photo of Serena and Colin, how easily it could be weaponized.

She closes her eyes, letting out a slow exhale, then taps ‘Delete’ again. I’m not fueling that fire.

A third tip: Blair Waldorf tried to sabotage Juliet Sharp at the ballet… but nothing came of it. Boring! Next time up your game, Queen B.

Jenny can’t help a faint smile. If only they knew what really went on. She wants to snark back—something about how Blair’s “game” is far from over—but she catches herself. Gossip Girl might thrive on drama, but Jenny’s tired of being the puppet-master.

She trashes that tip, too, then notices a follow-up from the same anonymous source, more malicious in tone, speculating about Blair’s finances. The vitriol makes her stomach churn. If she posts it, it’ll undoubtedly create a frenzy, but at what cost? Blair was the devil on her shoulder for so long, yet today, she was a reluctant ally. A messy ally, but an ally nonetheless. So Jenny discards that tip as well.

A tightness she didn’t realize she was holding in her shoulders eases. I guess my moral compass isn’t completely broken.

The tension easing from her shoulders is short-lived, however, because her phone pings again. This time, it’s not a Gossip Girl tip but a direct text from Eric:

E: Are you purposely ignoring all the UES drama today? Just noticed you trashed a bunch of tips…

Jenny’s stomach flips. Right. I’m not the only one who checks the inbox. She and Eric had quietly formed a partnership in running Gossip Girl—an alliance born of necessity after the constant threats they received during their time together at Constance and St. Jude's.

She quickly types back: J: Just don’t think we need to nuke them—yet. I’ll catch you up soon.

Her mind whirls with the reminder that she’s not alone in this. Eric can see every move she makes, every tip she deletes, every line of gossip she chooses to spare. For a moment, Jenny wonders if she’s risking their entire operation by letting personal feelings affect her decisions.

She’s still mulling this over when another text comes in, this one from Blair:

B: Well, that was anticlimactic. Ballet was uneventful—Juliet pinned everything on Vanessa. Typical. I’ll fill you in later.

Jenny can practically hear Blair’s exasperated sigh, and she imagines the perfectionist scowl that must be etched across her face. No bombshell reveal at the ballet, no epic meltdown from Juliet. Blair hates when her dramatic takedowns turn into a non-event. And Juliet blaming Vanessa? That’s a deflection no one saw coming—except maybe me, if I’d read the signs closer.

She types a quick reply, choosing each word carefully. J: That’s… unexpected. Good luck dealing with the fallout. Let me know if you need anything else.

She hesitates before hitting send. Any chance Blair suspects me? No… she’s too occupied with her war on Chuck. Jenny’s heart gives a jump as she realizes how easily she’s fallen back into the Upper East Side conspiracies—snooping in apartments, forging alliances, deciding what gossip to leak or bury. A part of her wonders if she’ll ever truly break away.

But for now, she slips her phone into her bag and turns to stare out the window. The city skyline shrinks in the distance, replaced by suburban stretches of green and quiet neighborhoods. A pang of longing tugs at her. There’s still time to walk away from all of this, she tells herself.

The train lurches slightly, and Jenny tries to focus on the flicker of telephone poles zipping by. She made the choice to delete those tips, to spare Blair, Chuck, and Serena—for now. I’m not the same Little J I used to be. Yet the hush of the train car does nothing to quiet the question echoing in her mind:

Can I keep playing Gossip Girl and stay the person I’m trying to become?

She doesn’t have an answer yet. But as she feels the weight of the flash drive in her purse—still holding that damning photo of Serena and Colin—she knows her double life is only getting more complicated. With Juliet on the warpath and Blair expecting her help, Jenny Humphrey’s return to Manhattan may have only just begun.

Chapter Text

Chapter Three | Mind Games

Jenny quietly leans on the island counter in the bright, expensive kitchen of the Van der Woodsen penthouse. She spent the night here after catching a late train from Hudson, under the pretense of a quick, family-oriented trip. Of course, her real reason is more complicated: she's meeting Tim Gunn today, hoping for an endorsement that might secure her a spot at Parson’s.

Around her, the hum of the city drifts through the windows—cars honking, footsteps on sidewalks. It's strange to be back in the heart of Manhattan, especially in this gilded penthouse that once felt like home. Jenny glances toward the living room, where her father, Rufus, is on a call, and Lily is reading the paper. She can hear Eric somewhere upstairs, rummaging through drawers. Even without Serena or Dan present, the penthouse still feels hectic in that familiar Upper East Side way.

Rufus finally ends his call and walks over to Jenny, placing a comforting hand on her shoulder. “Big day ahead?”

Jenny nods. “I’m meeting Tim Gunn in a couple of hours. He asked to see more of my designs. He might put in a good word for me at Parson’s.”

“That’s fantastic,” Rufus says. There is genuine pride in his eyes, but it's also tinged with concern. “You sure you’re okay being back here—after everything?”

He doesn't have to say it out loud: the banishment, the heartbreak, the endless drama. Jenny tries a brave smile. “I’ll be fine, Dad. I’m just focusing on meeting him. Then I’m back on a train to Hudson.”

Before Rufus can press further, Jenny’s phone buzzes with the distinctive tone of a Gossip Girl alert. She frowns. Coming back into the city always means stepping into a minefield of secrets and sabotage, and Gossip Girl blasts rarely brought good news.

She reluctantly swipes her screen. The new post hints at fresh drama involving Constance —rumors of sabotage, hints of insider blackmail regarding the new Queen Bee. Jenny’s stomach gives a nervous flutter.

She remembers how cutthroat and vicious the inner circle at Constance was during her short stint as Queen Bee. There was always someone to trying to sabotage the Queen, always someone trying to topple the hierarchy. She finds that she can't blame them, not anymore.

Jenny studies the blast and finds there's talk of potential “evidence” that could damage the new Queen Bee academically.

She sets her phone aside, uneasy. I’m not going to get dragged into this, she tells herself, even though she suspects fate has other ideas.

Lily enters the kitchen, smiling. “It’s nice to have you here, Jenny. Are you hungry? We have fresh croissants.”

Jenny forces a polite nod. “Thank you, Lily. I’ll just grab coffee—my appetite’s not great in the mornings.”

Lily offers a sympathetic look, perhaps sensing the tension that hovers around Jenny’s visits. Rufus clears his throat. “I can drop you at your meeting if you’d like.”

“That’s okay,” Jenny says. “I’ll take a cab. I don’t want to make a big deal of it.”

It almost feels normal for a moment—Eric descends the stairs, yawning, complaining about classes at St. Jude's, while Lily and Rufus discuss an upcoming charity benefit. Jenny sips her coffee, wishing she can freeze this slice of family life, untainted by drama or scandal. But deep down, she knows the Upper East Side won’t let her off that easily.

Eric plops onto a stool beside her. “So, we finally get you back for a day,” he teases. “And you’re already leaving for some fashion thing?”

“Meeting Tim Gunn,” Jenny clarifies, cheeks warming with excitement at the mention. “It’s sort of a big deal.”

“Sure is,” Eric says, shooting her a grin. "You'll knock it right out of the park, I know you will."

Jenny smiles gratefully at him, her nerves easing slightly, when suddenly the elevator dings, shattering her fragile peace. Her heart leaps anxiously the moment she hears Chuck Bass’s smooth voice drifting from the foyer. She grips her coffee, pulse racing uncontrollably. Despite everything, despite her mental preparations, she isn’t remotely ready to face him again. Their last encounter, still raw in her memory, is saturated with guilt, regret, and shame—the one night she’ll give anything to erase.

From her uneasy vantage point behind the kitchen island, Jenny watches Chuck exchange polite pleasantries with Lily. His face remains impassive, carefully masking whatever intent brought him here. The Upper East Side always finds ways to draw them all back into its tangled web, no matter how desperately Jenny tries to escape its pull.

Spread out carefully on the breakfast table in front of her is Jenny’s prized portfolio—her sketches meticulously prepared for Tim Gunn’s scrutiny. She planned quick revisions after coffee before heading out. Each design represents a lifeline, tangible proof of her worth and her future.

Chuck steps toward the kitchen, and Jenny instinctively shifts closer to Eric, desperate for his steadying presence. But Eric’s phone rings urgently, and with an apologetic glance, he excuses himself and heads upstairs, leaving her vulnerable and alone.

“Jenny,” Chuck greets evenly, his voice cool and controlled. “I heard you were back in town.”

She straightens her shoulders, fighting down the knot of awkwardness lodged firmly in her throat. Their shared past still hovers in the air, unspoken yet palpable. "I'm just here for a meeting," she replies cautiously, glancing at her sketches. "With Tim Gunn, actually."

Chuck moves toward the table, gently running his fingers over the edge of her portfolio. Jenny's stomach tightens further, sensing danger. "Parson’s, I assume?" he asks.

She nods stiffly, eager for this interaction to be over. "Yes, it's important. So if you don't mind—"

Before she can finish, Chuck smoothly scoops up her portfolio, flipping open the cover as though it were the most natural thing in the world. "Impressive," he remarks casually, leafing through the pages. 

Jenny tilts her chin defiantly, narrowing her eyes. “You’re giving me compliments now? Should I be flattered or frightened?”

“A bit of both, perhaps,” Chuck says smoothly. His eyes dance over her sketches, expression unreadable. “These are good. You've grown beyond Blair’s old hand-me-down headbands.”

Jenny’s cheeks flush slightly, but she hides it beneath a confident smirk. “I’ve had time to improve, without you or Blair getting in my way.”

Chuck raises an amused brow, seemingly impressed by her sass. “Touché. Still, you must admit, you’ve missed our little games.”

“I missed them about as much as a root canal,” she shoots back, eyes glinting playfully. “Now, could you kindly stop pawing through my future?”

Chuck snaps the binder shut with deliberate calm, holding it securely under his arm. “You know, these sketches really are perfect.”

Jenny narrows her eyes, heart thudding uncomfortably. "Perfect for what?"

He glances up, and in that moment, Jenny understands. It isn't personal—at least, not against her. She can see it clearly: this isn't about her designs, or even about her. It's about Blair. She's always known Chuck and Blair's games were intricate and unforgiving, but she didn't expect to be dragged back into them again.

Chuck tilts his head slightly, offering a small, conspiratorial smile. "You see, Jenny, Blair tends to react strongly whenever you're involved. And lately, I find myself needing her attention."

Jenny's stomach drops. She crosses her arms defensively. "You're seriously stealing my sketches just to get Blair to notice you?"

Chuck's expression shifts subtly—almost regretful for a brief moment, before settling back into practiced indifference. "Consider yourself a pawn in a much bigger game," he replies, his voice gentle but firm. "It's nothing personal."

Jenny crosses her arms, frustration and intrigue mingling in her expression. “So, what? I’m a shiny toy you wave around when Blair isn’t giving you enough attention?”

Chuck’s lips twitch in amusement. “You underestimate yourself, Jenny. You’re much more effective than a mere toy.”

She takes a step closer, narrowing her gaze dangerously, a challenge in her voice. “I almost forgot how charmingly manipulative you can be.”

He leans in slightly, voice dropping low and intimate. “Careful, Humphrey. That almost sounded like admiration.”

“Don’t flatter yourself, Bass,” she fires back instantly, her eyes glittering mischievously. “Now, give me back my sketches before this gets messy.”

He smirks softly, clearly entertained. “I’m afraid not. This method has the benefit of being immediate and effective. If you want these back," he gestures with the portfolio, "you'll need to retrieve them yourself. The Empire. Suite 1812."

The memory of her last time there floods her senses—the guilt, the confusion, the shame that had followed. Her jaw tightens, but she swallowed back the surge of emotions. "Chuck, please," she tries a different approach, softer this time. "Don't do this. This portfolio is my only ticket to the college of my dreams."

He seems to hesitate for a split second, a flicker of conflict passing through his dark gaze. But as quickly as it appeared, it vanishes. "I'll see you soon, Jenny," he murmurs, turning smoothly toward the elevator.

The soft ding of the elevator doors closing punctuates her panic. Jenny stands rooted in place, pulse racing, watching helplessly as Chuck disappears—with her sketches, her future, and any chance of escaping the Upper East Side unscathed. A sharp memory surfaces: the Empire suite, the quiet shame when she found the ring, the painful realization of how much she’d lost that night.

She closes her eyes briefly, fighting the turmoil rising in her chest. But beneath her panic lies a quiet resolve. 

She refuses to be collateral damage—pawn or not—in a war she wants no part in.

She'll go meet Tim Gunn without her portfolio, and try to impress him some other way. She was Jenny Humphrey, after all, and her passion for fashion knows no bounds.

Later that day, Jenny sits tensely at the corner table of a sophisticated café tucked quietly within Midtown Manhattan. Soft classical music hums from discreetly placed speakers, and around her, conversations buzz gently beneath the rhythmic clinking of porcelain cups. This serene atmosphere should ease her nerves, but instead it only heightens her anxiety. Her portfolio is nowhere to be found, stolen earlier this morning by Chuck, and Tim Gunn is due any second now.

She nervously checks her phone for the third time, biting her lip in frustration. If Chuck Bass ruins this for me, I swear…

"Jenny Humphrey?" a gentle, refined voice cuts through her spiraling thoughts. Jenny looks up abruptly, her heart skipping a beat as Tim Gunn himself, impeccably dressed in a tailored suit and tortoiseshell glasses, stands smiling politely down at her.

She quickly rises, offering a polite but nervous smile, extending her hand. "Mr. Gunn. Thank you so much for meeting me."

Tim Gunn gently shakes her hand, settling gracefully into the seat across from her. "Please, call me Tim. And of course, I’m happy to meet with you as a favor to Lily Van der Woodsen. She spoke very highly of you."

Jenny feels a pang of gratitude toward Lily, though the mention of her stepmother's favor also tightens the invisible knot of pressure around her chest. "I'm grateful to her, and to you," she replies earnestly. "I know you're very busy."

"Well," Tim says kindly, setting his espresso carefully onto the table, "I always make time to nurture promising talent. Lily assured me I'd be impressed by your latest designs. May I take a look?"

Jenny's pulse accelerates. She swallows the lump of panic rising in her throat, forcing her voice into an even, steady tone. "Actually, Tim, I—there’s a bit of a problem. My portfolio isn't... ready today." Her voice falters slightly as she tries desperately to hide her embarrassment.

Tim raises his eyebrows gently, expression carefully neutral. "I see," he says, clearly taken aback but too polite to show overt disappointment. "Lily mentioned you’d been preparing diligently."

"I was. I mean—I am," Jenny rushes to explain, anxiety prickling at her palms. "There was just... an unexpected complication." She feels her cheeks flush, her mind angrily replaying the smug smirk on Chuck’s face as he disappeared with her sketches.

Tim studies her for a moment, thoughtful and calm. "Complications happen. But you must understand, Jenny, Parson’s is fiercely competitive. It’s crucial to demonstrate reliability and professionalism, especially if I’m to advocate for you."

Jenny nods quickly, desperation seeping into her tone. "Absolutely. I completely understand. My designs are ready, and I promise they're good. It’s just...they were taken, briefly, by someone who thought it’d be amusing. A cruel joke," she adds softly, trying not to let her bitterness show too plainly.

Tim considers this revelation, clearly weighing her sincerity. After a moment, he sighs, adjusting his glasses thoughtfully. "Jenny, I see genuine potential in you. Lily wouldn't have reached out if she didn't wholeheartedly believe in your talent. Fortunately, I anticipated we might need a contingency. I've arranged for a formal interview at Parson’s tomorrow afternoon."

Jenny's eyes widen, hope swelling painfully in her chest. "Tomorrow?"

"Yes," he confirms firmly, leaning in slightly for emphasis. "And tomorrow, you'll need your complete portfolio without exception. This will be your opportunity to show Parson’s exactly what you're made of."

"I understand," Jenny breathes, relief mixing with renewed anxiety as the reality sinks in. I have less than twenty-four hours to get those sketches back from Chuck.

Tim rises gracefully, offering her an encouraging, professional smile. "I sincerely hope you manage to resolve your ‘complication’ promptly. You're talented, Jenny, but fashion rewards preparation as much as creativity. Don't disappoint yourself."

Jenny nods earnestly, managing a confident expression despite her fluttering nerves. "Thank you, Tim. I won't let you—or myself—down."

With a polite nod, Tim leaves her alone at the café table, the weight of her dreams resting firmly on her shoulders. Jenny exhales sharply, reaching immediately for her phone, only to find a text from Blair.

B: Drop what ever it is you're doing and meet me at Nate's apartment. We need to talk about the masquerade.

She hesitates briefly before replying, carefully crafting a believable lie.

J: Can't today, sorry. Have family plans I can't get out of. Let's regroup tomorrow.

Jenny knows it's risky to lie, but Blair can’t find out about her dealings with Chuck—not yet. She’s barely regained Blair’s tentative approval, and if she plays her cards right, she might finally lift the banishment that still hangs over her. Chuck remains a sore point in their fragile truce, and Jenny knows Blair would waste no time choosing sides—Chuck's side.

With a heavy sigh, she slips her phone away, stands from the table, and lifts her chin confidently. She strides purposefully out into the bustling Manhattan street, determination fueling every step. Hailing a cab, Jenny sets her sights firmly on the Empire Hotel.

Jenny steps out of the cab, gazing up at the towering luxury of the Empire Hotel. The familiar sight sends an uncomfortable chill down her spine. She stands frozen for a moment, memories flooding in, an uncomfortable swirl of regret, embarrassment, and something she’d rather not admit.

She shakes her head lightly, pushing those memories aside, and squares her shoulders defiantly. Just get the sketches and get out. Simple.

With her head held high, she walks purposefully through the lobby, her high-heeled boots clicking firmly against the polished marble floors. She ignores the curious glances from hotel staff, pressing the elevator button firmly. When the elevator finally arrives with a soft ding, she steps inside and taps the button for the eighteenth floor.

The numbers tick upward, each illuminated digit increasing her anxiety. Finally, the elevator stops, and Jenny steps out onto the plush carpeted hallway. She hesitates briefly outside suite 1812, her heart thudding in her chest. After a calming breath, she knocks sharply on the door.

A moment later, the door swings open, revealing Chuck leaning casually against the doorway. A smug, satisfied smile spreads across his lips as he meets her eyes.

"Well," Chuck drawls smoothly, eyes glittering with amusement, "I wondered how long it would take for you to come running."

Jenny crosses her arms defensively, lifting her chin with defiant sass. "Don't flatter yourself, Chuck. I'm only here because you stole something of mine."

He raises an eyebrow teasingly, stepping aside to let her into the suite. "Your sketches, of course. Excellent work, by the way, though your color palette could use some refinement."

Jenny breezes past him, rolling her eyes dramatically as she surveys the luxurious room. Her sketches rest deliberately on a nearby coffee table, arranged as if awaiting her inspection. She glares pointedly at Chuck. "Funny, I don't remember asking for a critique."

Chuck closes the door quietly, leaning against it with practiced ease. "Just offering friendly advice. After all, I’m helping you impress Tim Gunn. Aren't you grateful?"

She scoffs incredulously, snatching the portfolio off the table. "Grateful? You practically sabotaged me. And let’s be clear, your little plan to use me as bait for Blair isn’t going to work."

Chuck steps closer, voice low, amused yet oddly sincere. "Oh, Jenny, we both know Blair can’t resist reacting when you’re involved. You’re the perfect distraction."

Jenny's cheeks flush hotly, frustration and annoyance blending with reluctant admiration. "You really can’t help yourself, can you?"

Chuck shrugs elegantly, eyes dancing mischievously. "Admit it, you've missed being at the center of Upper East Side drama."

Jenny smiles bitterly, clutching her sketches protectively to her chest. "Sorry to disappoint, but these days, I'd rather be the one watching the drama, not causing it."

Chuck chuckles softly, stepping even closer. His voice lowers intimately, eyes locking onto hers. "Careful, Humphrey. Drama has a habit of finding you—no matter how far you run."

She holds her ground defiantly, though her heart quickens traitorously. "Only because people like you can’t seem to let me go."

Chuck opens his mouth to respond, a genuine intensity flickering in his gaze, but before the words can leave his lips, the suite door bursts open sharply, interrupting the charged atmosphere.

Both Jenny and Chuck whirl around as Blair Waldorf storms into the suite, eyes blazing with fury. Her piercing gaze flicks from Jenny—still clutching her portfolio—to Chuck, lips curling into an icy sneer.

"Well, isn't this cozy," Blair spits venomously. "Really, Jenny? You’re back barely a day, and already you’re with him? Family plans, my ass."

Jenny instantly steps away from Chuck, panic flooding her veins. "Blair, wait, it’s not what it looks like."

Blair's eyes flash dangerously, attention snapping to Chuck. "Oh, I know exactly what this is. You're both pathetically predictable. Although frankly, Bass, I thought your standards had risen slightly."

Chuck calmly folds his arms, seemingly unruffled, the corner of his mouth curving upward. "Come now, Blair. Jealousy doesn't become you."

"Jealousy?" Blair scoffs disdainfully. "Of Little J? Spare me. If you two insist on these juvenile games, do it without me. I’m done playing."

Jenny quickly steps forward, trying to reason. "Blair, please. Chuck took my sketches just to provoke you—"

Blair cuts her off sharply. "Save your breath, Jenny. I actually believed you'd changed. Clearly, that was a mistake."

Anger sparks within Jenny, mingling with hurt and frustration. "If you'd stop being stubborn for two seconds, you'd realize I have no interest in your twisted games!"

Blair’s expression darkens, fury now fully directed at Chuck. "You just couldn't resist, could you? Always stirring the pot, even if it means dragging her back into this."

Chuck remains coolly composed, lifting an eyebrow knowingly. "Please, Waldorf. Don't pretend you didn't secretly want this to happen."

Jenny takes a sharp breath, patience snapping like a frayed thread. "Enough," she interjects sharply, her voice strong and clear. "Yes, Chuck set this up—but I'm done being the pawn in both your games."

She shifts her intense gaze between Chuck and Blair, standing tall despite the tension in the air. "Unlike you two, I actually have something real beyond these twisted schemes. So fight your battles without me."

She moves swiftly toward the exit, pausing briefly at the threshold to throw Chuck one last defiant glare. "Find yourself a new puppet, Bass. This one's cutting the strings."

Without waiting for their responses, Jenny strides confidently down the hallway to the elevator. The doors slide closed behind her, and she leans heavily against the mirrored wall, heart hammering as the elevator descends. Anger, hurt, and betrayal swirl inside her, but beneath it all, there's something else: fierce, newfound pride.

She'd walked into Chuck’s game and left on her own terms. The Upper East Side could burn itself to the ground for all she cared. Right now, had a future to secure—and nothing would stop her.

Jenny sits poised and confident across from Tim Gunn and the esteemed Parsons panel, clutching her leather-bound sketch portfolio like a lifeline. She’s dressed impeccably, her carefully curated ensemble projecting exactly the kind of sophisticated yet edgy flair that defines her as a designer. The room is brightly lit, elegant, and professional, filled with polished wood, white surfaces, and a tangible air of anticipation.

"As you can see," Jenny continues, flipping carefully through her portfolio, "I’m heavily inspired by a blend of classic silhouettes and contemporary street style. I love combining textures and pushing boundaries while keeping the designs wearable."

Tim Gunn leans forward slightly, smiling warmly. "Very impressive, Jenny. Your vision is fresh, mature, and distinctly personal."

The panel members exchange approving nods, one woman jotting quick notes with an appreciative smile. Jenny’s heart races pleasantly. Maybe, after everything, this was truly her moment.

Tim gestures gently toward the garment bag beside her chair. "I think we’re ready to see your pieces now. Sketches are one thing, but execution is everything."

Jenny’s pulse quickens slightly, excitement fluttering in her chest. "Absolutely," she says confidently, rising and reaching for the garment bag. "I brought three garments that I feel best showcase my skills."

She carefully places the bag onto the presentation table, unzipping it slowly. "These are—"

Her words cut off abruptly as shock and horror flash across her face. Her hands freeze mid-motion, trembling slightly as her eyes widen. Her meticulously crafted garments—beautifully tailored dresses, jackets, and skirts—are marred with glaring red spray paint. Ugly words slash brutally across the expensive fabric:

"Bitch."

"Cheater."

"Social-climber."

And worst of all, right across her proudest creation, a black satin evening gown she had spent countless sleepless nights perfecting, the phrase: "Little J."

Her heart plummets painfully. The world seems to tilt, panic and humiliation battling for dominance. Jenny’s face flushes hot, embarrassment scorching her cheeks. Blair Waldorf’s fingerprints are all over this, even if they’re not literally visible. Only Blair could wield cruelty this elegant, this precise.

"Jenny?" Tim’s voice is gentle yet startled. The panel members exchange worried, uncomfortable glances. "Is everything alright?"

She tries desperately to collect herself, turning slightly to block their view as she frantically tries to rearrange the ruined garments. "I—I don’t understand. This wasn’t—these weren’t like this before…"

Tim rises slowly from his seat, concern evident in his eyes. "Jenny, if something’s happened, we can talk about it."

Her hands tremble as she desperately tries to smooth the creases of the vandalized silk, her vision blurred by tears she refuses to let fall. Suddenly, a tiny slip of stationery flutters out from within the layers of fabric, landing softly onto the polished table.

Jenny’s breath catches. She swiftly picks it up, dread filling her chest as she unfolds the elegant paper, the handwriting unmistakably Blair’s:

"Welcome back, Little J. Consider this a lesson in knowing your place. Our truce is off. xoxo."

Anger floods her veins, momentarily drowning out the humiliation. Her jaw clenches, but she knows there's nothing she can say that won’t sound petty or childish. Tim Gunn’s voice gently interrupts her spiraling thoughts.

"Jenny," he says softly, genuine regret coloring his tone, "Perhaps it's best if we take a break. Clearly something unexpected has occurred."

She nods numbly, quickly folding the ruined garments back into the garment bag, unable to meet their disappointed gazes. "I'm so sorry," she manages quietly. "I—I understand."

"Thank you for coming in, Jenny," Tim says, compassion still evident in his tone. "We'll…be in touch."

Jenny gathers her things quietly, head held high despite the shame burning through her veins.

She leaves the room swiftly, stepping out into the bright hallway of Parson's with a shaky breath. Tears burn her eyes, and she grips Blair’s cruel note so tightly it nearly crumples in her hand.

But beneath the sharp sting of humiliation lies something deeper and more troubling. Her truce with Blair is clearly over—and that realization brings another wave of dread.

Blair’s refusal to trust her now means Jenny can't warn her about Juliet's true agenda and scheme against Serena. Without Blair’s help, Juliet's twisted plan might succeed, and Serena could pay the price for their renewed feud.

Stepping outside onto the bustling Manhattan street, Jenny leans against the cool stone of the building, her heart heavy. Blair may have intended only to sabotage Jenny's future—but inadvertently, she might have just endangered Serena’s as well.

Jenny swallows hard, determination returning even stronger despite the hurt.

She can't give up—not now. Serena’s safety depends on it. She'll have to take matters into her own hands, starting with the masquerade ball.

Chapter Text

Chapter Four | Hidden In Plain Sight

The Van der Woodsen penthouse still smells like whatever Diptyque candle Serena has most recently decided represents her inner truth. Tonight, it's something with notes of “Italian Cypress” and “French aristocracy.” Jenny barely notices it.

She's too busy praying the elevator won't ding.

But it does.

Soft and accusing.

She steps out like a ghost, black hoodie zipped halfway up, dufflebag in hand. Her boots barely make a sound on the marble floor — a skill she’s picked up in the kind of houses that have more cameras than people. She’s rehearsed this part. Calm. Quiet. Fast. No drama.

Unfortunately, Serena van der Woodsen isn’t someone you can sneak up on.

“What the hell—” Serena turns from the hallway mirror, still halfway through curling the third section of her perfectly golden hair. Her eyes widen as she catches sight of the girl in black standing where Vanya the doorman should’ve buzzed first. “Jenny?”

Jenny freezes. The script in her head instantly evaporates.

“Hi Serena,” she says, quiet and steady. “Don’t freak out.”

“Oh, I will,” Serena says, already moving. “Are you stalking me now? You’re not supposed to be anywhere near this building—hell, this borough!”

“I—” Jenny tries, then swallows. “I had to come.”

“You’re not supposed to be here,” Serena snaps again, mascara wand still in hand. “You're not even allowed in Manhattan right now. What, did Blair forget to send out the restraining order this time?”

Jenny clenches her fists around the dufflebag. “You’re in danger.”

Serena actually laughs. A short, sharp, you’ve got to be kidding me sound.

“Wow. It took, what, fifteen seconds? That’s a new record even for you.” She turns back to the mirror like this is just another minor inconvenience in her shiny, tragic life. “Let me guess. This is about the masquerade? You saw the GG blast and got jealous? What—you couldn’t stand being irrelevant for one more night?”

Jenny stares at her reflection in the mirror. Tall, glowing, every strand of hair is arranged like a conspiracy. Serena doesn’t look scared. She looks annoyed.

“It's Juliet,” Jenny says, low and steady. “She's planning something. At the masquerade. Something bad. I think she wants to ruin you. And she has all the ammunition to succeed this time.”

Serena’s mascara pauses mid-swipe. She doesn’t say anything for a second — and for a moment, Jenny thinks that maybe she's getting through. But then Serena blinks and gives a soft, scornful smile.

“Oh, that’s rich,” she huffs. “Reinvention season really hit, huh? Jenny Humphrey, guardian angel. Coming to save me from the consequences of being hotter than Juliet Sharp.”

“It’s not jealousy,” Jenny bites out. “It’s a setup.”

“Right. And I’m supposed to believe you care what happens to me?”

Jenny’s chest starts to ache. She isn’t even angry. Not really. Just… tired.

“I wouldn’t be here if I didn’t.”

That makes Serena pause. But only for a second. “No,” she says. “You’re here because you can’t stand it. That no matter how much damage you cause, somehow I still get invited to the ball and you don’t. That people still talk about me. That they don’t talk about you at all.”

That one stings. Because it isn’t entirely wrong.

Jenny exhales slowly. “You really think I’d come all this way just to sabotage you again? No—I came to stop you from getting hurt.”

“You’ve already hurt me,” Serena snaps, stepping closer. “Do you even remember what you did last year? Or are we just wiping the slate clean every time you get a new eyeliner look?”

Jenny’s fingers tighten around her bag. “You think I don’t feel guilty?”

“I think you don’t feel anything unless it gets you attention.”

“That’s not fair.”

“Oh, please.” Serena rolls her eyes, mascara wand still in hand like a weapon. “You’re obsessed with me. You always have been. You wish you were me.”

“I used to,” Jenny admits, blunt. “But now I just want to keep you alive.”

“What are you even talking about?”

“Juliet and Vanessa—”

“Oh, of course. Vanessa’s involved.” Serena laughs again, but it's sharp now. Bitter. “What is this, the Revenge of the Underdogs? You’re all so desperate to matter.”

Jenny steps forward. “You need to stay home tonight.”

“No. You don’t get to tell me what to do. Not now. Not ever.”

“I’m trying to save your life.”

“You’re trying to rewrite history. But guess what?” Serena tosses her hair over one shoulder. “I’m not your redemption arc.”

Jenny’s jaw clenches. “I don’t need redemption from you.”

Serena doesn’t answer. She reaches for her phone.

Jenny’s body moves before her brain does. She grabs the phone first, quick and clean, and slides it into her hoodie pocket. Serena blinks like she can’t process what just happened.

“What are you doing?” she snaps. “Give that back!”

“I can’t let you go,” Jenny says. “They’ll hurt you. Or worse.”

For a split second, Serena looks almost… scared. But then she remembers who is standing in front of her. “I can take care of myself.”

“No, you can’t,” Jenny snaps back. “Because you still think every threat is about who gets to sit next to Anne Archibald at lunch. You don’t know how bad this is.”

Serena looks at her like she's disgusting. “You don’t get to do this. You don’t get to pretend to be the hero.”

Jenny steps back. “I’m not trying to be.”

“Then what are you trying to be?” Serena hisses. “Relevant? Pitiful? Or just me, again?”

Jenny stares at her for a long time.

“You know what’s sad?” Jenny says quietly. “You think everyone’s obsessed with you, but the only one who keeps making it about Serena van der Woodsen is Serena van der Woodsen.”

That does it. Serena’s face hardens. She sets down the mascara wand with precision, like someone preparing to throw a knife. “You’re a toxic little parasite,” she says flatly. “You ruin everything you touch. You ruined Nate. You ruined my family. You ruined—”

“Myself,” Jenny cuts in, her voice rising. “Yeah, I know. I’ve heard the speech. Congratulations, you can rehearse it for Vanity Fair next.”

Serena lunges forward and tries to snatch her phone back. “Give it to me, Jenny!” she shouts, grabbing for her wrist. The two of them collide — a flash of blonde and black, perfume and panic — shoving against the marble counter. Jenny’s elbow knocks into a glass perfume bottle; it crashes to the floor, shattering between them.

“Stop it!” Jenny gasps, twisting out of Serena’s grip. “You don’t understand—”

Serena shoves her again, harder this time. “You’re insane! You need help!”

Jenny catches her wrist, adrenaline surging. “You’re not going to that party.”

“Watch me!” Serena jerks free, spinning toward the door.

Jenny doesn’t think. She just moves.

In two quick strides she reaches the hallway ahead of her and throws the bathroom door open, yanking Serena inside by the arm. Serena’s gasp echoes like a gunshot—equal parts fury and disbelief—before Jenny shoves her all the way in and slams the door shut. The lock clicks. Hard.

Instantly, Serena pounds against it. “Jenny? Are you seriously—JENNY—OPEN THIS—”

Jenny doesn’t answer. She doesn’t move.

Inside the bathroom, Serena is screaming now, threats echoing off the tiled walls.

“You’re insane! You’re going to regret this! You’ll regret this!”

Maybe. But not tonight.

Jenny steps into the dressing room and unzips the garment bag hanging on the back of the door. She’s seen it earlier—pale blue satin, floor-length, off-the-shoulder, classic Serena. The mask is hanging beside it, sapphire and delicate like a crown someone forgot to finish. It shimmers even in the dim light.

She pulls the dress over her head and lets it settle on her frame. She isn’t as modelesque. Won’t be as graceful. But in heels, behind a mask, under the right lighting?

It should be enough.

Jenny moves to the mirror and stares at herself. She looks ridiculous. And terrifying. And perfect.

She takes a shaky breath.

“I’m sorry,” she whispers again. Not to Serena. To herself. 

To the version of herself that she really did want to become, but that won't see the light of day.

Then she dumps her dufflebag and slips Serena’s phone deeper into the matching clutch before walking out the front door, not looking back.

Behind her, Serena is still shouting.

And for once, Jenny doesn’t answer.

Outside, the night air hits her like a slap—cold, glittering, full of promise and ruin. She opens her own phone, thumb trembling only once before she steadies it. The Gossip Girl submission box waits, hungry as ever.

She types, then hits send.

Spotted: Dan and Nate at war over S. But who will she choose at the Masquerade? Let the games (and the gossip) begin.

She attaches the video—her in Serena’s gown, descending the Van der Woodsen staircase like she owns the city—and watches the upload bar crawl to completion.

One second later, she feels Serena's phone buzz. The blast is live.

If this is the only way to keep Juliet’s eyes on her, fine. She'll get her hands dirty for one more night.

Jenny slips the device back into Serena's clutch, pulls up the hood of her borrowed coat, and steps into the waiting car.

By the time the city realizes what it has seen, it will already be too late.

The Empire has always smelled like new money pretending to be old.

Tonight it’s bergamot and bourbon and a hundred bodies moving like a rumor. Strings sob softly over the speakers while a DJ pretends he isn’t being paid triple to keep it classy. Chandeliers throw diamonds onto the marble, and masks turn friends into strangers, turn strangers into threats. It’s perfect. It’s awful. It’s the Upper East Side in a single breath.

Jenny steps out of the car in Serena’s pale blue and feels the whole city hold a mirror up to her. Heads turn. Security glances at the guest list, then at the mask, then at the dress, and open the velvet rope without asking a single question. Of course. Status is an outfit in this town.

The ballroom swallows her. A thousand low conversations braid together. Waiters drift like patient sharks. A photographer pops a flash at the wrong moment and apologizes in a whisper no one hears. 

She holds Serena’s clutch like a detonator and keeps moving.

She isn’t here for the party. She’s here to find Juliet.

Juliet Sharp, the girl with a smile as fake as her supposed trust fund. The one who made a sport out of Serena’s destruction and dragged everyone else down with her. Jenny knows she’s here somewhere, hidden in plain sight. That’s what makes her dangerous. And that’s why Jenny came. To stop her.

From the upper floor balconies, light scatters down like diamonds in water. Below, the ballroom glows—gold, white, and venomous. Jenny scans faces beneath masks, looking for a tell. Then she sees her: blonde, gleaming, Serena-shaped. Her heart lurches. For a split second she thinks it’s the real thing, that Serena somehow escaped. But the posture is wrong. The laughter too practiced. That isn’t Serena. That’s Juliet.

Juliet moves like she owns the night, her imitation perfect—hair curled, dress identical, the exact shade of effortless deception. She leans into Nate’s arm near the bar, then drifts toward Dan by the orchestra pit, switching masks between them like an actress hitting marks. Two Serenas in one room. Jenny’s blood runs cold. The plan is worse than she thought. Juliet’s making them both believe they’re the one.

Jenny adjusts the sapphire mask. She walks slower to make herself visible, to make the decoy believable. If Juliet thinks Serena’s already here, maybe she’ll make a mistake.

A gloved hand brushes her arm. “Serena,” Vanessa’s voice purrs, smugly familiar, “you look stunning.”

Jenny tilts her head, gives her Serena’s soft, amused smile, the one you use on boutique clerks and ex-boyfriends. “Funny,” she says, letting her voice float, warmer than it feels. “You too.”

Vanessa’s eyes narrow, scanning her posture for a tell—but the illusion holds. Satisfied, Vanessa nods politely and drifts away, already pulling out her phone to text someone. Jenny doesn’t need to guess who.

Good. Keep texting her, Vanessa. Keep feeding her updates. The longer you two think I’m Serena, the more time I have to stop whatever you’re planning.

A burst of laughter ripples across the room. KC’s voice cuts the air from somewhere near the dais, bright and bored: “Welcome, saints and sinners—behave yourselves accordingly.” 

Another titter; a waiter swings past balancing a tray of champagne like a halo. Jenny takes one, more for camouflage than courage. The flute’s stem is cool in Serena’s hand. No—hers. She tries not to think about the bathroom door. Tries not to think about Serena’s voice ricocheting off tile. You’re going to regret this. Later.

And then—of course—Blair Waldorf, stitched like a threat in red velvet, appears out of a cloud of perfume and disdain.

“Trying subtlety now, Serena?” Blair’s tone is bright and vicious, a pretty ribbon around barbed wire. “How refreshing.”

Jenny manages to turn exactly the way Serena would: chin lifted a quarter inch, bored, pretty. Serena never drops her head to meet you; you raise yours and hope she notices. Jenny gives Blair the briefest, coldest sweep of a glance and then keeps walking.

It’s a small thing. It detonates like a bomb.

“Excuse me?” Blair’s smile doesn’t move; her voice fractures. “Did you just—” She angles herself into the path of the dress, into the path of the myth, unwilling to be ignored on her own battlefield. “Serena.”

“Blair,” Jenny finally says, pulse racing. She makes the mistake of liking how the word tastes when she isn’t afraid.

“Your new thing is walking away, I see,” Blair purrs, drifting closer, letting the lace of her glove trail the air near Jenny’s bare arm without touching it. “Very chic. Very… grown. Almost as if you learned not to cause a scene.”

Jenny’s eyes flick over Blair’s shoulder — searching the crowd, scanning for another glimpse of Juliet. She spots the second blonde shadow moving near the punch bowl, laughing too loudly with Dan. Still pretending. Still perfect. The sight makes Jenny’s pulse sharpen. Blair is a distraction she can’t afford right now.

She could cut Blair with a hundred words. She swallows instead. “Excuse me,” she says, and steps to the side. She doesn't have time for this.

Blair’s smile tenses. “Excused,” she says sweetly, then leans in, breath brushing Jenny’s mask. “Try not to spill anything tonight. Literally or figuratively. I'm not in the mood to clean up one of your messes, S.”

It lands. It always does. Jenny’s chest tightens with heat she doesn’t want to examine—shame, anger, the memory of silk ruined by red spray paint. She doesn’t give Blair the pleasure. She tips the champagne, sips nothing, and keeps moving.

“Mm,” Blair says, louder now. “Subtle. Refreshing. Looks good on you, Serena. I'm impressed.”

Jenny lets the words follow her into the crowd and die there. She doesn’t look back. If she does, she is not Serena. She moves into the glitter, into the swell of strings, into a world that would eat the real her for lunch and ask for dessert. She lets the music pin her body upright, lets the dress choreograph her breath, lets the city believe its favorite lie.

She makes a point of being seen and not seen. Of being Serena and not Serena. Of existing just enough to pull every eye that matters toward her and away from a bathroom door at the penthouse on Fifty Fifth Street.

Jenny keeps moving, tracing Juliet’s path from afar. She watches Juliet whisper something into Nate’s ear, sees him smile like he’s hearing an old secret, then watches her drift toward Dan again, a chameleon in heels. Jenny’s jaw locks. If she can just intercept her, just confront her, maybe she can stop whatever’s about to happen. But before she can close the distance, a cluster of photographers cuts across the floor, blinding her with flash. When her vision clears, Juliet’s gone.

Up the grand staircase—she drifts like mist. The second level is less crowded, the air thinner, the music slightly muffled, like someone draped velvet over a speaker. From here the ballroom looks like a jewel box full of ants. The balcony rail is draped with gauze and midnight-blue velvet, a theatrical flourish designed for dramatic speeches and private sins.

Juliet is nowhere in sight. Just Vanessa, still on her phone. Jenny curses under her breath. She’s losing time. Then she hears voices from behind the velvet curtain—familiar ones—and for one dangerous moment, she forgets why she came.

Jenny doesn’t mean to find them. She just means to breathe. But the curtains on the far side of the balcony are imperfectly closed, one edge furled back by a lazy draft, and voices drift through in a cadence she knows better than she wants to.

“…and you’ll tell me again it was nothing,” a woman says, brisk and careful, like she is defusing a bomb and refuses to say the word bomb out loud.

“And you’ll pretend it mattered less because I said it during sex,” a man replies, wry and weary, the vowels dipped in smoke.

Blair. Chuck.

Jenny freezes, as if the syllables have teeth.

Through the slit in the curtains, she sees only fragments: the clean angle of a jaw, the perverse glint of a cufflink, Blair’s hand resting on a table littered with the kind of champagne coupes no one actually enjoys. Private suite energy—someone’s tried to make two chairs and a small table feel like a confessional.

“I’m not pretending anything,” Blair says, and the words land like a door left gently open. “I heard you. I’m not crazy.”

“Not about this,” Chuck says softly. It’s almost kind. It would be romantic if it didn’t make Jenny want to throw something off the balcony and count the seconds before it hits the marble.

Blair’s fingers flex like brief lightning. “Did you mean it?”

Silence digs its heels in.

Jenny’s pulse climbs her throat. It’s ridiculous that she cares. It’s ridiculous that this—two people who built a world entirely out of cruelty and gifts—can make her feel something like vertigo.

Chuck clears his throat as if the words weigh more than the glass in his hand. “Yes.”

A beat. The music below licks at the silence, uncertain. Jenny imagines the chandelier holding its breath.

Blair exhales in a ragged little laugh that tries very hard to be smooth. “Well. That was… injudicious.”

“Blair,” he says, and she hates that his voice knows how to say it. “It wasn’t a tactic.”

“That would almost be worse if I believed you,” she says. She sounds exhausted. She sounds young. Jenny hates that, too.

“I meant it,” he repeats, and there’s something in the sentence that sounds like surrender. “I mean it.”

Jenny’s skin prickles. The old anger rises, slow and oceanic. They ruin her for sport—blowtorch her future because a room full of strangers needed a show—and here they are, snatching at something pure like it’s a silk ribbon they get to tie around their own throats for fun. A gift. A private grammar of tenderness. Something they would deny others but allow themselves. Of course.

Blair’s mask is off inside the little alcove. Jenny sees her profile, sharp and beloved by cameras, soften like wax under a match. “Then say it to me,” she says, almost whispering, like she doesn’t want to. “Not to the room. Not to the game. To me.”

Chuck’s hand trembles where it rests on the table. He’s quieter than she’s ever heard him. “I love you.”

Jenny’s mouth goes dry. The words tilt the floor.

Blair closes her eyes. It takes her one second, two, to find breath again, to put her mask back on with muscle memory alone. “Then we accept the consequences,” she says, composure snapping back into place like a bracelet. “Whatever they are.”

“Together,” he offers, reckless, hungry.

“Don’t get sentimental,” she says mildly. “It doesn’t suit you.”

Jenny steps closer before she knows she’s moving, toes at the edge of the velvet, breath held like a fist. Below, the ballroom churns, oblivious. Above, two people tell themselves a story where they are the only two people alive. She hates it. She hates them. She hates the part of her that wants to believe anyone gets to have that without cost.

Her hand finds the curtain.

This is petty. This is childish. This is wrong.

She thinks of the black satin gown wrecked by a spray can, of Tim Gunn’s kind eyes tilting with disappointment, of the way Blair’s note cut like silk and left a welt. Welcome back, Little J. Know your place. Of Chuck’s fingers skimming her portfolio as if it were his to move, his to decide, as if he could bend her future into a bouquet to carry to Blair. She thinks of Serena pounding the bathroom door with words she will regret later and might never apologize for. She thinks of choosing to be the lightning rod so someone else doesn’t burn.

Consequences.

Jenny slips her fingers under the velvet and yanks.

The gauze screams on its track. The curtain flies back, a rip of midnight pouring daylight onto a secret. The private alcove becomes a stage. Blair and Chuck are revealed in a frame of embarrassed gold: her mask in hand, his mouth half-open, both caught between intimacy and performance, between before and after.

Silence rolls over the balcony like weather.

Then the ballroom below inhales as one.

A hundred phones lift, moths to the flame. Anne Archibald is a perfect oval of appalled at the foot of the stairs, pearls stiff at her throat, hand halfway up as if she’d been mid-charming wave and forgot what to do with her wrist when reality arrived. KC is already calculating angles. A journalist tries not to smile and fails behind a napkin.

Jenny doesn’t breathe. She doesn’t move. The world has that crisp, winter-morning sound where everything is louder because it’s too quiet.

Blair is the first to recover. She does it like a queen in an execution painting, calm and inevitable. The mask goes on in one graceful motion. She rises. She turns. She descends one step as if she’s practicing for a coronation she just learned she cannot have.

“Anne,” she says, sugar and steel. “What a pleasant surprise.”

Anne blinks. Her smile is polite acid. “Blair.”

Chuck steps forward, untouchable smile in place—expensive suit, expensive face, expensive damage. His gaze cuts the crowd like he’s choosing who to forgive first. “Ladies and gentlemen,” he calls, lazily amused, “welcome to the moment you were promised.”

Laughter bubbles, uncertain. It’s what the room wanted, and it’s what the room will punish.

Jenny stays in shadow, mask a mirror, heart a hammer.

“Now we’re even,” she whispers to herself, and it isn’t triumph. It’s something colder and sadder that tastes like surrender.

Blair reaches Anne; the crowd parts for her like it always will until it won’t. Jenny can’t hear the first sentence, only the shape of an explanation—composure stretched thin over panic. Anne shakes her head once, sharply, the way you shoo a fly. Jenny hears this part: “Your image, dear. The board… it simply isn’t compatible.” It lands like a judge tapping a gavel with a smile.

Blair’s chin lifts half an inch, the imperceptible recalibration of someone who refuses to be seen falling. “I understand,” she says, and means I will destroy you later and you will thank me for it.

Chuck says something to KC. Cameras pop like gunfire. On the far side of the floor, Vanessa keeps her phone low, thumbs moving fast—likely reporting to Juliet who is still lurking somewhere. Jenny watches her just long enough to know that whatever’s coming next, the pieces are still in motion.

Jenny makes herself small. The balcony railing presses into her ribs. For a second, she thinks she might be sick. Not from the guilt—fine, there’s a sliver of it, a hairline fracture under the pride—but from the sudden, dizzying tilt of all that glitter pointing back at her. She did this. She chose this. She pulled a thread and the dress fell off the mannequin in front of everyone. The room hums, hungry. It will need another bite soon.

Fine. Let it chew on them. She has other work.

She doesn’t see the waiter until the tray kisses her shoulder.

A flash of red—cold, sticky. Liquid arcs, a single crimson ribbon catching the light before it meets silk. The punch blooms across Jenny’s mask, splattering the sapphire like a crime scene.

“Oh my God,” Vanessa gasps, hand flying to her mouth. It’s too fast to be an accident and too smooth to be anything else. “Serena, I am so, so—” She reaches for a napkin she doesn’t offer. “Let me help—”

“I’ve got it,” Jenny says, steady and dry, even as sugar syrup clings to the filigree and drips off her jaw. The mask is wet against her skin now, fruity and wrong.

“Humidity in here is a killer,” another voice purrs, arriving with the confidence of a queen wave. Juliet. In a different dress and mask now. She materializes at Jenny’s elbow as if she were always meant to be there and smiles like a key fitting a lock. “Good thing I brought a spare.”

She holds up a velvet mask—midnight blue, identical cut, identical sparkle. Or nearly. Jenny can’t tell if the difference is in the dye or in the way Juliet’s eyes gleam when she says, “Fresh start?”

The joke is obvious. The threat is casual. It’s a trap wrapped in courtesy. Jenny could walk away. She could say no. She could. But Serena’s phone is a weight in her clutch, and Juliet is watching for flinch and guilt, and Vanessa’s eyes are already slick with the thrill of a trap working. The only way out is through; the only way to keep them convinced is to drown properly.

Jenny takes the mask. The velvet is cool in her gloved hand. “Thanks.”

Juliet leans closer, the fake intimacy of girlfriends in public. “I’d hate for your night to be ruined,” she says, soft and bright. “Wouldn’t you?”

Vanessa’s eyes are steady now, the tremble gone. “We should get you cleaned up,” she adds. “KC wants to pull you onstage for a toast, remember?” A lie that sounds true because this room was built to flatter it.

Jenny nods like Serena would: bored, accommodating, already elsewhere. She turns so they can't see her face as she lifts the drenched mask, and for a split second the sugary scent spikes—thick, artificial, something beneath it that isn’t fruit at all. A chemical sweetness that isn’t a flavor so much as a warning.

She swaps them. The spare slides into place.

The first breath is fine.

The second is not.

It happens in layers, like a curtain lowering in slow motion. The perfume in the room tips toward metallic; the strings in the speakers sound watery, as if the bow is cutting through fog. The chandelier above her doubles, then triples, then smears into a galaxy she didn’t ask for. Her skin goes hot, then cold. The floor tilts half a degree and refuses to correct itself.

“Better?” Juliet asks, and her face is too close to make sense.

“Perfect,” Jenny hears herself say. Her voice sounds like it came from the next room.

She tries to step left—toward the nearest pillar, toward air, toward control—but her heel snags on nothing and her knee doesn’t get the message. The crowd becomes a blur of generous strangers and eager witnesses. Someone laughs; someone else says Serena's name in the wrong key. The mask is the only thing holding her face together.

Juliet’s hand lands on her elbow with the exact right amount of pressure to look like kindness. Vanessa appears at her other side, already murmuring something soothing that could double as instructions. “Let’s get you backstage. You don’t want photographs like this.”

Like this. Dizzy. Ruined. Vulnerable.

Jenny’s stomach rolls. She swallows hard and tastes sugar and a hint of something metallic. She grips Serena’s clutch so tightly her palm hurts. She thinks, Phone. She thinks, Door. She thinks, Breathe.

Somewhere, a phone vibrates with a location pin pulsing like a heartbeat.

They shepherd her through a seam in the crowd and along the wall—past the floral arch, past the DJ, past the place where power pretends to stand still. The service corridor yawns open, cooler air brushing her bare shoulders like a mercy. The music dims to a distant heartbeat. The carpet underfoot gives way to rougher flooring; her steps make a more honest sound.

“Almost there,” Vanessa says.

“Fresh air,” Juliet adds. “You’ll feel better in a minute.”

The hallway tilts again. The lights overhead hum. Jenny blinks hard, tries to focus on something fixed—the EXIT sign, the red slash of it. Her vision stutters. For a brief, brilliant second, the mask slips a fraction on her cheekbone and she sees Vanessa’s face change.

Not pity. Not triumph.

Recognition.

Vanessa’s eyes sharpen. A flare. The kind you get when the math suddenly stops adding up. “Wait,” she says, too soft for anyone else. “That’s—”

“Keep walking,” Juliet hisses, but it’s not to Jenny, and no amount of horror on Vanessa’s face adds up to conscience. “Now.”

Jenny’s heel skids. Her shoulder hits the wall. She drags air through her teeth and it tastes like dust and endings.

“She—Juliet, that’s Jen—”

“Do you want to stand here and get caught? Or do you want to live?”

For a heartbeat Vanessa looks like the kind of person she thinks she is. Then, she looks like the kind of person she is with Juliet in the room. She nods. They turn. Their skirts whisper like rumor. They’re gone, already birds flying low.

Jenny takes the first step because falling is just walking with worse PR. She thinks, At least Serena’s safe. It feels like a prayer and a lie and a promise.

The alley is a different city: wet brick, trash sweet as rot, a sky the color of a bruise. The door hums shut behind her. The cold hits like a hand to the face; it helps for exactly one second and then the floor decides it would prefer to be the ceiling. She makes it three steps into the dark and the dark steps back.

Her back finds the wall. Her knees decide not to participate in upright living. She slides down, silk arguing with asphalt, palms scraping old rain. Her breath goes shallow, quiet. She can still hear the party—muffled hysteria, distant applause, Manhattan saying more, more to itself like a spell.

Her clutch is under her fingers. Serena’s phone is a weight like fate. She thinks about unlocking it, typing something that proves she was here. She thinks about doing nothing at all. Her vision stutters—on, off, like a bad light. Sirens somewhere. A car door. Laughter ringing, wrong.

Her last clean thought is an apology she doesn’t know who to send to: Serena? Herself? The part of her that still wants to live someplace where dresses don’t get you killed?

Heels slice the quiet.

Not Juliet’s staccato. Not Vanessa’s hesitant shuffle. Faster. Familiar.

“Jenny?”

A voice breaks on her name. Not elegant. Real.

She tries to lift her head; the world tilts again. The mask has slipped to her cheek, ridiculous and tender. Warm hands catch her shoulders, grip steady, shaking. Perfume that isn’t Diptyque, for once. Something floral and human.

“Oh my God—Jenny.” Closer now, threaded with panic. “Hey. Hey, look at me. Please.”

Jenny blinks. The alley rearranges itself around the voice. Her vision keeps trying to turn off, but she drags it open, stubborn. Blonde hair. A face she used to envy like it was a career path and a life she used to want like addiction.

“You weren’t supposed to be here,” she breathes, words slurring into each other like they prefer to be quiet.

“And you weren’t supposed to save me,” Serena says, and for the first time all night, there’s nothing cruel in it. Only fear. Only fury—for Jenny, not at her. “I should have believed you. I'm so sorry. I’ve got you. Do you hear me? I’ve got you.”

Jenny lets her eyes fall shut because the city won’t stop spinning and Serena’s voice sounds like an ambulance that knows her name.

The dress is cold. The hands are warm. The night finally stops pretending to be glamorous and just is dark.

The world goes dim. Then it goes.

Chapter Text

Chapter Five | A Friend

The world comes back as a hum.

Not voices. Not faces. Just that sterile electric sound that makes everything feel like it’s happening in a fishbowl—white light pressing down, sheets too stiff to be kind, the quiet beep that insists a heart is doing its job even when its owner isn’t sure she wants it to.

Her mouth tastes like sugar and pennies.

Jenny opens her eyes to ceiling tiles that look like graph paper and blinks until the corners stop strobing. The memory hits out of order: velvet, chandeliers, the weight of blue satin; an alley that tasted like rain and asphalt; a mask that smelled wrong, sweet and chemical like fruit that forgot how to be food. And a voice—not her own.

I’ve got you. Do you hear me? I’ve got you.

Serena. Not a dream, then. She didn’t imagine the bathroom door slamming, the lock clicking, the way Serena’s fists made fireworks on the other side of painted wood while Jenny climbed into a life that wasn’t hers to save the one that was.

The room is too white to be honest. The kind of white that pretends nothing bad happens here if it’s documented in the right font.

On the rolling tray: a copy of The Spectator, folded so the headline leans at her like a dare—“Ballroom Secrets: Billionaire Heir and Socialite Caught in Masquerade Mayhem".

Cute.

A vase of lilies sits on the windowsill, elegant as an apology. Lily’s attempt at calm, bottled in glass and water.

Jenny swallows. Her throat burns. The beep keeps time. She flexes her fingers just to prove she can and feels the tug of tape and IV and consequence.

“Ugh,” she rasps to no one, “I feel like shit.”

The monitor agrees—cheerful little beeps like congratulations on your poor decisions—and somewhere in the hallway, someone laughs. The sound doesn’t feel like it belongs to this floor. It belongs to parties and marble and girls wearing other girls’ faces.

Jenny forces a swallow and her tongue drags over the roof of her mouth like it’s still made of velvet. A nurse she doesn’t know appears and disappears like a well-meaning ghost, checking her chart, her pupils, the tape on her IV. She says a cluster of words—lucky, stable, rest—and leaves Jenny with a cup of water and a permission slip for pain if she wants it.

She doesn’t know how long she stares at the lilies before she realizes the air in the doorway is different, charged with a particular kind of chaos she could identify in her sleep. Family.

They file in like a funeral procession that lost the map.

Serena first—mascara smudged into something almost human, golden hair pulled into a messy knot as if vanity learned how to prioritize. Her eyes are wide and dry in the way of someone who ran out of tears on the ride over and decided to save face for later.

Lily behind her, perfect posture, perfect coat, perfectly trembling hands tucked into the sleeves so no one can see them shake.

Rufus takes the foot of the bed like a position, arms crossed so tight you could bounce a quarter off his jaw.

Eric hovers like a low, kind lighthouse—present without crowding, making sure everyone sees the rocks before they hit them.

Dan leans on the wall the way only a Brooklyn boy can, trying very hard not to hover and absolutely hovering anyway.

“You scared the hell out of us, Jenny.” Rufus doesn’t shout. He doesn’t need to. “One minute, as far as I’m aware, you’re in Hudson with your mom, the next I’m getting a call saying you were found in an alley in Manhattan—” He stops. He doesn’t say wearing Serena’s dress. Jenny can hear it anyway. “—unconscious.”

“Hi, Dad.” Her voice scrapes like sandpaper. “I didn’t mean for any of this to happen.”

Serena drags the chair closer without asking and sits, the metal legs squeaking against tile. “You locked me in a bathroom,” she says softly, like she’s trying out the sentence to see if it fits in her mouth.

“I was trying to save you.” Jenny's fingers worry at a loose edge of tape on the IV before she remembers not to be an idiot and flattens her hand over her thigh instead. “I know that’s not going to sound—”

“You did,” Serena says, and a small disbelieving laugh breaks across her face. Her eyes flash wet and clear at the same time—Serena’s favorite trick. She shakes her head a little like she can dislodge the last twelve hours. “You did.”

That’s as far as anyone gets for a minute. The room is crowded with the weight of all the things they don’t say in this family because they’re too busy performing for each other—what they mean to do, what they shouldn’t have done, who they wish they were.

Eric sidles closer to Jenny's other side and sets a hand, warm and careful, over the thin blanket. “You look like shit,” he says, voice soft enough to be a blanket itself.

Jenny huffs a laugh that hurts. “Wow. Tell me how you really feel.”

“That is how I really feel. I say it with love.”

“I’ll take it.”

Lily clears her throat—ladylike, controlled—as if she can smooth the air with etiquette. “We’re grateful you’re awake,” she says, and somehow makes it sound like a prayer she’s folding in with her napkin. “The doctor said there were…substances in your system. Nothing fatal,” she adds quickly, catching Rufus’s flinch, “but enough to make you very ill.”

“Yeah.” Jenny closes her eyes and the room tilts for half a second. “That’s because Juliet drugged the mask.” She open them again and let the words fall into the space they’ve cleared. “She thought I was Serena.”

Serena stiffens.

“I took your phone and your dress,” Jenny reminds her, because she knows Serena remembers and she hates herself anyway. “I needed Juliet to look at me and see you. That was the point. But the mask—she swapped it on the balcony. It smelled like perfume and something else. And then…” Jenny makes a small gesture with her hand, like she can mime the floor tilting out from under her. “Ta-da.”

“You shouldn’t have been there at all,” Rufus says, and the line of his mouth can cut glass.

“Dad,” Dan warns, but there’s something dark in his eyes too, something he’s saving for Vanessa.

Serena’s staring at her like she can rewind the night and fix it with sheer disapproval. Then her face changes—some private math clicking into place. 

“I only found you because you took my phone,” she says, and Jenny swears the heart monitor gets louder, ratting her words into a rhythm. She glances at The Spectator, ashamed and annoyed at the same time, which is also one of Serena’s favorite tricks. 

“You—” She breaks off, shakes her head like it’s rude to make Jenny relive her own walk of shame. “It doesn’t matter. I got out of the bathroom. I used a bobby pin,” she says, dry, and tilts her head toward Eric. “He had to talk me through it outside the door like a YouTube tutorial for petty criminals.”

Eric lifts a hand, saintly and smug. “Thank you. I accept this award on behalf of every gay kid who learned to break into a bathroom because the straight girl crying on the other side couldn’t even pick an outfit.”

“Hey,” Serena says, but with a smile. She looks back at Jenny. “The minute I had a phone again, I tracked mine. I thought—God, I don’t know what I thought. That you were being dramatic? That you wanted attention?” 

She scrubs a hand over her face and smears whatever was left of her mascara. “I was wrong. I saw you in the alley. I heard you. I didn’t—” Her voice cracks and she swallows it like a pill. “I’m sorry I didn’t believe you.”

The thing about Serena is she makes apologies like a debut—full eye contact, a little breathless, sincere enough to make the rest of the room soften without permission. It could be a skill or a flaw. Today it feels like a lifeline.

“I’m not great at asking for belief,” Jenny says, trying for dry and mostly landing on tired. “I kind of burnt through the trust of everyone in this city.”

“You also kind of wore my dress,” Serena says, and the corner of her mouth lifts. “We’re… fine. We’re fine.”

“Stop saying ‘we’re fine’ like you’re daring the universe to disagree,” Eric mutters, and Serena swats at him, missing by design.

Rufus is still standing like a man waiting for a verdict he already knows he hates. He drags a hand through his hair. “Juliet drugged you,” he says, like if he names it, he can contain it. “And Vanessa helped her.”

“Vanessa helped her,” Dan repeats, every syllable neat as a staple. “Of course she did.” He pushes off the wall, scrubs a hand down his face, and laughs a short, humorless thing that makes Jenny want to fix everything Vanessa broke in him when she crashed into his life and tried to drag him down with her. “Did she also draft a manifesto about how it was for the greater good? Because if I know Vanessa—”

“—she wrote it on recycled paper and signed it with a heart,” Eric says. “Sorry. Too soon?”

“Never,” Dan says. “It’s never too soon to roast my ex for attempted manslaughter.”

“Attempted manslaughter isn’t a thing,” Serena murmurs, because she can’t not be the centre of attention even when she’s bleeding sincerity. “That’s just… you know what, it doesn’t matter. She’s awful.”

“I’m willing to make it a thing,” Dan says, steady again, mouth twitching. He looks back at his little sister and the sarcasm leaves his eyes like a tide going out. “Are you okay?”

The question is stupid and necessary. Jenny nods anyway. “I will be.”

“Good,” he says. “Then maybe later we can talk about your newfound passion for method acting.”

“I wore a dress and a mask. I didn’t join a cult.”

“You locked Serena in a bathroom.”

“Fine,” Jenny concedes. “A small bathroom cult.”

Eric makes a scandalized noise that turns into a laugh he tries to smother. Lily gives him a look that says not in the hospital and fails to suppress the glint in her own eyes. Even Rufus cracks at the edges.

“You saw them,” Jenny says to Serena, because the room is getting too light for the truth they still need. “You said you heard something.”

Her nod is sharp. “Yes. After I tracked my phone and found you, I doubled back inside to get help. I was on the mezzanine when I heard them. Juliet and Vanessa. They were moving fast. I don’t think they saw me.” She stops, and the anger that moves across her face is clean, almost clinical, like the moment a doctor decides on surgery. 

“Vanessa said, ‘That wasn’t Serena.’ Juliet said, ‘It doesn’t matter. No one will know until it’s too late.’ And then—” She looks at Jenny and there’s apology layered under the fury—at herself, at the world, Jenny isn't sure. “Juliet laughed. Like it was a joke. She said, ‘Fresh air will do her good.’”

“Oh my God,” Lily says quietly, hand bracing on the back of Serena’s chair like she can hold her daughter and the world upright at the same time. “They intended to harm you. Deliberately.”

“Welcome to Manhattan,” Jenny says, and immediately hates that her mouth still makes jokes in the dark.

Eric squeezes her hand through the blanket. “You’ve been in Manhattan, like, twice this month and you have one dramatic event left on your punch card. Please be more boring.”

“I tried boring.” Jenny deadpans. “It didn’t take.”

Rufus exhales like he’s been holding his breath since she was born. “We’re going to the police.”

“And say what?” Jenny asks. “That the girl who hates my step-sister handed me—dressed as said step-sister—a mask that happened to make me collapse? There’s no proof. It was a ballroom full of masks.”

“We have eyewitness testimony,” Rufus argues, chin up.

“From Serena. In a room where half the guests have her face on their vision boards,” Jenny shoots back, gentler than it reads. “Juliet’s smart. Vanessa’s… thorough. If there’s anything physical, it won’t be obvious.”

“We can have the mask tested,” Lily says, frowning into the middle distance that must be full of donors and favors. “I can make calls.”

“I didn’t keep it,” Jenny says, hating how small her voice goes when she has to disappoint her step-mom. “I dropped it somewhere between the elevator and the floor deciding it wanted to be my best friend.”

“Of course,” Lily murmurs. “Of course.”

Silence folds over them for a breath. The monitor keeps score. Outside the door, a cart rattles past with the rattle of an ordinary life Jenny doesn’t remember how to live.

She looks down at her wrist and the tape and the bruise blooming underneath and thinks of all the other marks she's left on people—sharpie and lipstick, rumor and truth. She built a machine that's chewed up girls like herself and then stepped into its mouth and dared it to bite.

“You said the mask was switched,” Dan says, and the way he says it, careful and measured, tells her he is building a case whether he admits it or not. “Where?”

“Upstairs. Balcony.” She hears the music in her head again, varnished and vicious. “Vanessa got a waiter to deliberately bump into me. She made a show of spilling something and apologizing and then—” She mimes the gesture, a little flick, a magician’s trick. “Juliet was there with a ‘spare.’ The first breath was fine.”

“And the second?” Eric asks.

“Wasn’t,” She says, and they don’t need more than that.

Rufus looks like someone rearranged his bones into a man who fails his children. “You’re coming home,” he says abruptly, voice flattening, father’s authority doing what it does when it doesn’t know what else to do. “I’m not letting you stay here another night after—after all this. And you're definitely not going back to Hudson where your mom apparently lets you run around loose.”

“Rufus,” Lily says gently, “she needs medical rest, not confinement.”

“She needs boundaries, Lily. Look where not having any got her.”

“This isn’t about blame—” Serena starts.

“It’s about responsibility, Serena,” he snaps, and then guilt comes crashing in right behind it.

“I’m right here, you know.” Jenny doesn’t raise her voice. She doesn’t have to. It threads into the space exactly where it hurts. “You can talk to me, not about me.”

Something in Rufus’s face falls open and you can see the man who never expected to be anyone’s father and then became one twice. He scrubs his knuckles against his mouth and stares up at the fluorescent lights like they might have advice.

Dan steps forward, soft enough to slip under the fight. “Dad, she nearly died. Maybe we can save the lectures for when she isn’t hooked up to an IV.”

“You think I don’t know that?” Rufus says, and it comes out like a plea.

“I think you’re scared,” Dan says, and then he looks at Jenny, and his voice gentles in a way that always makes her feel five and safe and seventeen and furious, all at once. “And she’s scared. And we’re all pretending yelling makes it better.”

The silence that follows is heavier than shouting. Lily reaches over and takes Rufus’s hand and squeezes, a small clean thing that feels like a truce. He squeezes back.

Dan turns back to Jenny and lifts a shoulder like he’s trying to dislodge the last twelve months. “You did what you thought you had to do,” he says. “I don’t agree with how, but… I get why.”

“You believe me?” she asks, even though he just said he did, even though desperate isn’t a color she wears well.

“Always have.” He gives her a crooked approximation of a smile. “Even when I wish I didn’t.”

The laugh that bubbles out of Jenny surprises her ribs. “That’s extremely rude.”

“Good,” he says. “I’m aiming for consistent.” He glances at Serena, then back to Jenny. “Just… next time, maybe text instead of impersonating someone at a gala?”

“No promises.”

They hold each other’s eyes for a second and some of the tight coil in Jenny's chest loosens. It’s not fixed. It’s never fixed. But it’s not going to break today.

“I’ll have your room made up,” Lily says, brisk again, already rearranging the world for her step-daughter. “Rufus, I'll call Alison and tell her we're moving Jenny back to the penthouse. She’ll be safe at home with us.”

“Home?” Jenny echoes before she can help it. The word lands in her mouth like a marble you have to roll around to make sense of.

“Yes,” Lily says simply. “Home.”

Serena squeezes Jenny's fingers, a little too hard like she needs the anchor more than Jenny does. “You can wear my dress again,” she says, deadpan, and Eric groans.

“I’m confiscating all masks,” he says. “From everyone. We are a mask-free home now. Metaphorically and literally.”

“Eric,” Serena says sweetly, “your entire wardrobe is a mask.”

“That’s called taste,” he says, scandalized.

Rufus stares at the ceiling like he might start negotiating with God. “I’m making waffles.”

“You always make waffles,” Dan says.

“I’m making more waffles,” Rufus says, doubling down like a man who knows his only weapon is batter and love. He looks at his daughter, finally, directly. “You’re coming home with us,” he says, and this time it isn’t an order. It’s a request. A hope.

“Okay.” Jenny lets it sit for a second so it doesn’t feel like a surrender. “Okay.”

Something unclenches around the bed. The nurse ghosts back in to check vitals and remind Serena she isn’t the doctor no matter how many times she says her dad's one. Lily steps out to make calls in a voice that could part elevators. Eric announces he’s going to smuggle real coffee past the nurses’ station and gets shushed by three different people at once. Dan shifts into logistics—what time, what ride, what sweater Jenny will definitely pretend to hate but steal anyway.

Rufus pretends not to tear up and fails. Jenny pretends not to notice and fails.

She looks over at the lilies again because it’s easier than looking at all of them and all of the ways she's failed them and loved them and ruined their night. That’s when she notices the other arrangement—lower, denser, tucked behind the lilies like it’s trying not to be obvious. Peonies and white roses knotted with a ribbon the color of old money. There’s no card.

“Who sent those?” she asks, nodding toward them because she doesn’t trust her arm not to awkwardly flail and rip out her IV like she's auditioning for a tragedy.

Lily follows her glance. “Oh.” She moves closer, fingers brushing the bow like she knows what expensive feels like by touch alone. “They arrived at the penthouse very early. No signature. Vanya brought them down himself.”

“Vanya?” Serena said. “Well now I’m suspicious.”

“You were already suspicious,” Eric tells her. “It’s how your eyebrows stay so arched.”

“They’re not from me,” Rufus says, which: obviously. “And before anyone asks, they’re not from your grandfather either. He sends fruit baskets because he assumes no one has teeth.”

“Maybe Blair,” Serena says thoughtfully. “Guilt and good taste are her love languages.”

“Or Nate,” Dan says. “He has a tragic habit of being a golden retriever with good botanical taste.”

Jenny lets the guesses pass over her like a breeze. The roses do not care who was named. They sit in their modest, expensive silence and allow themselves to be pretty. Later, she knows—the way you do when the city has trained you to expect the twist—the answer will arrive and rearrange something you think you know. For now, they're just flowers. For now, that's enough.

Rufus shifts forward, forearms braced on his knees. “We’ll bring you home,” he says again, calmer. “We’ll make soup. We’ll… watch terrible movies. We’ll do anything that doesn’t involve masks.”

“I’m actually… I think I should stay at the penthouse for a couple days,” Serena says, glancing at Lily and then at Jenny. “So she has someone to glare at when she tries to sneak out.”

“I don’t sneak,” Jenny says.

“You wear other people’s faces,” Serena returns, gentle, and then her hand finds Jenny’s and stays there. “But being you is enough."

Eric’s phone buzzes. He flicks it on, reads, then raises his eyebrows. “Dorota says Blair wants to send over her personal doctor.”

“No,” Jenny says instantly.

“Yes,” Dan says, simultaneously.

Serena squeezes her hand. “We’ll tell her thank you, but the hospital has plenty of doctors and none of them will try to diagnose you with ‘poorly chosen accessories.’”

“Which is considered a real illness in this city,” Dan adds sarcastically.

Rufus huffs something that thought about being a laugh and gave up halfway. He looks like a man who has run out of ways to stand and sit and is starting to learn how to hover. He reaches a hand toward Jenny’s hair and thinks better of it. She doesn’t mind that he stops. It's enough to watch him try.

He finally stands, kisses her forehead like the past hasn’t made that complicated. “We’re going to let you rest,” he says. “We’ll be down the hall. If you even think about moving, I will know.”

“That’s frightening,” Jenny says.

“I’m frightening,” he quips, and fails to hide his smile.

Lily touches her wrist—light, anchoring. “You are loved,” she says, and not like a slogan. “Don’t try to argue.”

“I don’t have the energy,” Jenny says, which is both an acquiescence and a relief.

Eric winks his soft-lantern wink and whispers, “Are you okay if I go yell at someone?” he asks, sweet as arsenic.

“You’re going to yell at Vanessa,” Jenny guesses, because of course.

“Maybe,” he says, lilting, and then sobers. “Carefully.”

“Carefully,” Jenny whispers back.

It's Dan's turn now. “Hey,” he says, and when Jenny looks up, his face has the softness it only gets when he’s not being watched. “We’ll handle the yelling. You handle the not dying.”

“I’ll do my best,” she says, and it lands like a vow she can maybe keep this time.

Serena stays a second longer, after the others drift into the hall and the door clicks soft behind them. The room remakes itself around their breathing.

“I’m sorry,” Serena says quietly. “For not believing you. For saying… what I said.”

“Yeah,” Jenny says. She considers biting it back and doesn’t. “That was brutal.”

Serena winces. “I know. I get threatened and I turn into a mirror ball with knives. I’m working on it.”

“We’re all working on something,” Jenny says. “I’m working on not impersonating you at events.”

Serena laughs with genuine horror. “God, please.”

They look at each other like two girls who have run out of costumes. It's almost funny how much they resemble themselves when they finally stop trying to be the story.

“How did you know to come?” Jenny asks, the question sneaking out before she approves it. “I mean, besides the phone.”

“Honestly?” Serena’s mouth twists. “I heard my own voice in my head and hated it enough to chase you down.” She glances at the door. “And you slid the bobby pin under the door like a white flag just before you left.”

Jenny snorts. “Subtlety is dead.”

“Subtlety lives in Paris and refuses to text us back,” Serena declares, and leans in to kiss her temple, soft as a promise. “Rest. I’ll be just outside, terrorizing nurses into bringing you ice chips.”

“Thank you for saving my life,” Jenny says, before she can decide not to.

Serena’s eyes are wet again. “Thank you for giving me the chance.”

When the door clicks behind her, the room exhales. The lilies throw their quiet at the window. The roses by the radiator sit in their short glass like an intention. Jenny stares at them and lets the speculation slip off one petal at a time. Blair? Nate? Someone else. It shouldn’t matter, and it doesn’t, yet it does. It's stupid, and it's the shape of something true: the city speaking in gifts it didn’t sign.

She lets her head fall back against the pillow and listens to the monitor keep time against the day. She remembers the bathroom door, the velvet mask, the alley. She remembers Serena’s voice dragging her up out of the dark like a rope. What she does not remember—refuses to—is the feeling that all of this will just keep happening to her. That's a lie she has to stop telling herself if she wants to make it through the year with any part of her that still belongs to her.

“Okay,” she says to no one. The word tastes like resolution small enough to swallow. “Okay.”

In the hallway, the low, familiar murmur of the Van der Humphreys braid and unbraid—Rufus insisting on soup, Lily insisting on decency, Eric insisting on caffeine, Dan insisting on finding Vanessa and giving her a piece of his mind, and Serena insisting she’ll be where Jenny could see her shadow under the door if she looks. The city outside does its glittering, guilty thing. Somewhere, a florist records a sale with no name attached.

Jenny closes her eyes. She isn’t a saint because she’s done a dangerous thing on purpose. She isn’t a monster because she’s wants credit for it. She is a girl with stitches you can’t see, in a room that smells like money pretending to be mercy, with a family that loves her wrong and loud and right.

And when she sleeps, finally, it is without a mask.

Night slips in sideways.

When Jenny wakes again, the room has traded its bright, polite daylight for the kind of dark that hospitals do on purpose; lamps turned low, everything soft enough to convince you rest is a choice. The lilies have gone from glossy to ghostlike. The other bouquet—peonies and white roses—looks richer under lamplight, the ribbon throwing a faint gold line across the wall like a horizon someone drew in the wrong place.

Footsteps pass. A nurse appears, kind in the way of people who’ve learned how to be invisible. She checks the lines, the numbers, the little universe of beeps. Then she sets a familiar rectangle on the tray and slides it toward Jenny with two fingers.

“Found this with your things,” she says. “Only a few percent left.”

“Thanks,” Jenny murmurs.

The phone is cracked along the corner. Her thumb unlocks it on muscle memory. 3AM. Missed calls stack from Hudson—Mom, Mom, Mom—and a scatter of texts from Eric in three different tones (soothing, scolding, meme). A text from her Dad: I’m on stand by if you need me. And even a text from Scott: Heard the news from Dan, hope you're getting some rest!

Her mouth curves without permission. Then the buzz comes, soft, almost polite. A new badge, a familiar icon. 

Gossip Girl: New Tip Received.

Of course. The city never sleeps and neither does the monster she made.

For a second she just looks at the notification pulsing like a heartbeat and considers doing the brave, healthy thing: delete, block, erase. She even drags it halfway toward oblivion. But then the handle catches her attention.

From: B_Brooklyn93

She stares at it for another beat, as she considers saving herself the next twenty disasters by tapping one tiny trash can icon. Then curiosity—old, electric, hungry—wakes up in her chest and sits up straight.

She opens it before she can change her mind.

Subject: Legacy.

There are bigger ghosts in Manhattan than everyone thinks. Some wear masks that never come off. Start with Bass Industries, Project Silver, 1993. You’ll find what they buried.

— A friend

The room tilts a degree—not the drugged kind, the moral kind. The word Bass lands in her chest with the weight of a paperweight and the promise of a storm.

Jenny reads it again, slower. 

B_Brooklyn93. 

The handle snags her brain on all the right barbs. B like Blair or Bass. 

Brooklyn like hers, the borough everyone thinks they can map and never really knows. 

Ninety-three like the year she was born.

She scrolls for context she knows won’t be there and finds none. No attachments. No one has ever sent Gossip Girl something like this—no homecoming queen takedown, no grainy bathroom kiss, no petty vendetta wrapped in a punny subject line. Legacy is the opposite of a blast. It’s a letter slipped under a door at three a.m.

A friend.

Blair wouldn’t call herself that. Not like this. And not to anyone who wasn't part of her inner circle. Serena hates Gossip Girl and would rather die than submit a tip. Dan would use too many words. Nate would barely use any words. Chuck… Chuck would never send an email. He’d send a storm.

This voice is something else. Clean. Corporate. Cold. The kind of sentence structure you get from boardrooms and NDAs. The kind of year you choose on purpose.

Why now? 1993 was a lifetime and seventeen years ago. If this is a prank, it’s a very expensive one. If it isn’t, what does Bass Industries have to do with ghosts in Manhattan?

“Project Silver,” she says into the dim, and the word tastes metallic, like a coatrack in winter. She doesn’t know the project. Never heard of it. But she does know that Bass Industries makes it worse. Makes it interesting.

She flicks to Notes, copies the text, pastes like muscle memory. Project Silver. 1993. Bass Industries. A breadcrumb in a jar. Insurance for a day when she might pretend she isn’t going to pick it up and follow it anyway.

She stares at the tip for a second, and deletes it from the inbox. Then deletes it from the trash. Before Eric wakes up and sees it in the morning.

Because she’s done. That’s the story she’s telling herself. She is a girl in a hospital bed with a family who has forgiven her and a wrecking ball for a past, and the last thing she needs is to go spelunking in Bass corporate archives for a ghost.

And yet.

Her gaze drifts back to the flowers. The lilies are lovely and obvious. The roses are quiet and unnervingly specific, ribbon tied in the color of old money. No card. No claim. Just intent.

“You’ll find what they buried.”

The line moves across her brain with the slow inevitability of something that matters. She rests her palm over the phone and can feel its small, stupid warmth. She is not opening it again. She is not.

She is done being Gossip Girl.

She is.

The thought sits in her mouth like a pearl and a pill, both hard to swallow. Behind her eyelids, blue satin falls like water; a bobby pin glints in a bathroom lock; a masked girl laughs and hands over poison with pretty hands. Jenny turns on her side as much as the lines will let her and tucks her fingers under the pillow like she could hide the itch and the evidence.

Sleep comes back as it pulls her under, the handle floats once behind her eyes, rearranging its letters into something she doesn’t see in time. B_Brooklyn93. A friend from her borough with teeth.

The monitor keeps time. The city keeps secrets. And in the dark, a breadcrumb sits where she left it, patient as a grave.