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What Might've Been

Chapter 44: Chapter 43 - Thinking About It

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“What do you say, sweets? Rory? Rory?! Hey, kid!”

Lorelai eventually had to resort to literally poking Rory in the shoulder to get her attention. Her daughter flinched as if she just got an electric shock, pulling one earbud out. Lorelai rolled her eyes.

“How long have you been listening to the tunes?” she asked. “Because you missed a really good ramble about the state of our kitchen and the out of date stuff in the fridge,” she advised with mock annoyance.

“Sorry,” Rory apologised all the same. “I, er... I was distracted” she said, sitting up against the headboard and staring at the Discman in front of her.

Lorelai was a little bemused, unsure as to what strange effect the contained CD must be having on her baby girl. Rory hadn’t been crying, but she didn’t looked exactly happy either. It was all very strange.

“Can I?” said Lorelai, picking up the Discman and pressing the open button.

Rory nodded then looked away as Lorelai came to realise what the issue was. The CD in the machine wasn’t anything bought from the store or even borrowed from Lane, it was distinctly home-made and the handwriting on it was all too familiar.

“We’ve been making mixes for each other forever,” Rory confessed. “But that one was special, the first one he made after we... we decided to be together,” she swallowed hard. “I didn’t even know it was in there, I misplaced the Discman until yesterday and then I just hit play on whatever was in it.”

“Well, honey, you could’ve turned it off if it upset you...”

“I wasn’t upset, I’m not,” she shook her head. “It was nice to hear it, to remember. That sounds so weird, ‘to remember’ as if me and Jess being together was so long ago. It feels like forever and no time at all at the same time. Is that weird?”

“Time is a strange thing,” Lorelai shrugged. “There are times when I look at you and I can’t believe it’s more than sixteen years since that fateful night...”

“Splits on a crate of dynamite, I know,” Rory smiled slightly, as her mother reached out to touch her hair.

“I trained you well, young Padawan, but seriously, sometimes it’s as if the last sixteen years just zipped by. Other times, I feel like stuff that happened last week was forever ago. I don’t know why time is that way. It just is, I guess.”

“I guess,” Rory echoed, eyes wandering to the Discman and it’s contents again.

Lorelai soon realised she wasn’t going to get much of a conversation out of Rory right now. Sometimes a girl needed to be alone with her thoughts. She had complete confidence that if Rory did need to talk, about Jess or anything else, then she would let her know. She got up to leave and got a bit of a surprise when Rory called her back.

“Mom? That box of stuff that we made...”

“The Jess box?” Lorelai checked.

Rory nodded her head.

“You didn’t really throw it out, right?”

“Hall closet, top shelf,” her mother winked.

A grin overtook Rory’s face as she leapt off the bed and hugged her mom tight around the neck, whispering a thank you before diving off to the closet. Lorelai slipped by her, saying she would be upstairs if she was needed and just to holler. Rory pulled the cardboard box down from the top shelf and dragged it into her room, depositing it awkwardly on her bed, half the contents spilling out already.

Calling it the Jess box was kind of inaccurate. This was by no means everything she owned that Jess had bought for her, shared with her, certainly not everything she had that reminded her of her best friend/ex-boyfriend. That had turned out to be an impossible task. Pretty much every item she owned would have ended up in storage if she tried to ditch all things Jess-related. In the end, Rory and Lorelai had boxed up only items that had a romantic link to Jess. Rory had asked that it all be tossed in the trash, maybe even burned to cinders. She knew she should be mad at her mom for saying she would carry out her wishes and then just hiding it in the closet, but now she was glad. There was no indication she and Jess would ever go back to dating, Rory wasn’t even sure yet if she wanted that to happen, but she suddenly felt very nostalgic for the items in this box.

Rory smiled as she pulled out her blue dress from the Chilton dance, the night she and Jess had sort of started dating. It was actually the next day when they made the decision to give a closer relationship a try, but she still counted the dance as their first official date. It had ended with kissing after all. Under the dress, she found more CDs Jess had burnt for her, a few silly love letters that she knew he would be embarrassed to admit he ever wrote, and a couple of first drafts of letters she wrote to him too, as weird as that might seem to anyone else. The teddy bear Jess won for Rory at the Winter Carnival sat next to movie ticket stubs and the book he bought her for Christmas. So many happy memories brought a wide smile to Rory’s face that wavered only a little when she realised that part of her relationship with Jess was over now.

They were friends again and it felt so good to have Jess back in her life. Living without him was weird and awful. Rory never wanted to do that again, and yet she couldn’t help but wonder if they had made a mistake in giving up on their romance too soon. The way they could talk to each other, about anything and everything, the link they had, it had just disintegrated when they got closer. She got stupidly jealous of Shane and Paris. Jess got similarly annoyed by Dean, long before that one kiss ever happened. When they were together, Rory and Jess seemed to forget how to talk and went straight into full make out. It wasn’t that she didn’t enjoy the kissing and all, but it seemed to take something away from them. It made their relationship into something new but in doing so they lost what they used to have. If only they could have retained their friendship when they fell into a boyfriend-girlfriend relationship. Rory wondered now why that had been so hard, if maybe going into that situation again they could han
dle it better having already made all the mistakes before. Her hand actually reached for the phone, as she gave serious consideration to calling Jess and asking why they hadn’t tried harder, why they hadn’t been more determined to make things work. She got as far as the speed-dial button but no further before throwing the phone across the room where it landed with a bump on the rug.

Rory and Jess were friends again, no more, no less. She had told Miss Patty as much just yesterday, and yet Rory also recalled a moment at the Indepedance Inn that very afternoon, falling on top of Jess on the couch. His fingers had been in her hair and his lips so close to hers as the heat of his body radiated into her through their clothes. It had been painfully disappointing when nothing else happened, and yet she knew it had to be for the best.

With a sigh, Rory stuffed the contents of the Jess box back inside its home, adding the CD from her Discman to the pile and putting another music selection into the player instead. Moving to sit at her desk and finish off some homework, she had her back to the box and her mom’s Greatest Hits of The Bangles pounding in her ears, but still Rory thought of Jess. She couldn’t seem to stop.


Monday was a blessing for Rory. School was a great distraction from too many unwanted thoughts, that was for sure, and by the time she got to lunch she had a grin on her face thanks to Mr Medina’s latest English assignment, followed by some complex math problems that were sure to occupy her mind lest it start to wander again. Of course, she ought to have known she was doing too well, and Paris seemed determined to ruin an otherwise perfectly good day as she slid into the seat on the opposite side of the table.

“I need your help,” she said seriously. “And yes, I’m aware that is a bizarre statement of fact when it’s coming from me to you, but what can I say? You’re the only person who might actually be able to help me since you have actually had a boyfriend recently. Granted, you’re not together anymore, but you still had him, and Jess is a decent guy worth mentioning in this context...”

“Paris, slow down!” Rory ordered her, hands making a cutting motion so her friend would just stop for a second. “Geez, I know I can talk fast but that was insane. Take a breath, tell me one thing at a time. You need my help. With what?”

“I have a date.”

Rory’s eyes went a little wide at the sound of that confession. Paris looked automatically offended.

“Gee, thanks, Gilmore!” she huffed. “As if I wasn’t feeling self-conscious enough already!”

“I’m sorry, Paris. Really, I am,” Rory apologised immediately. “Um, that’s just the last thing I was expecting you to say. Not that you wouldn’t get asked out, I mean, of course you would,” she back-pedalled fast when she realised what she implied.

Paris rolled her eyes.

“It’s fine. It’s not like I ever got asked out before, so your shock is accurate if not insulting,” she sighed.

“Okay, well... okay,” Rory repeated awkwardly. “I guess I’m just a little confused as to why you need my help with a date? Unless... Um, did Jess...?”

“No,” Paris cut in fast, actually laughing a little as she tucked her own hair back behind her ear like a nervous gesture. “Me and Jess, we get along, he’s great to talk to, but I never really thought he would like me that way anyway,” she shook her head. “Honestly, the dark and broody thing would probably get old pretty fast. That and the beatnik worship, and his being completely crazy over you. Anyway, it’s actually Tristan that asked me out,” she smiled wide, practically blushing as she admitted the truth.

Rory kept her reactions in check this time, not reacting to Paris’ continued insistance that Jess was in love with her, and determined not to look too shocked and offend her friend any further. It was a mind blowing realisation though, to think that someone like Tristan DuGrey, who could pretty much have any girl in school, would ask out Paris Gellar. He had to have his reasons, but still Rory hadn’t got to the answer she wanted.

“Again I ask, why would you need my help in dating Tristan?” she tried.

Paris rolled her eyes one more time.

“You have experience,” she said crossly, like it was just so tiresome that Rory didn’t get it without a full explanation being given. “Of going on dates, I mean. I think we’re pretty far off anything else right now... at least I assume so. You’ve actually been out with a guy, you know how to dress and act, how much make up to wear, that kind of thing.”

“Well, yeah, I guess I do,” Rory considered. “But wouldn’t Madeline and Louise be better at...”

“Please! Like I want them giving me advice!” Paris complained. “They would have me dressed like a Hooters waitress, fluttering fake eyelashes, and practically begging for a reverse cowgirl.”

Rory tried not to giggle at the phrasing or vomit at the imagery. She shook her head.

“Well, I can help with dating attire and stuff, of course,” she smiled then. “But... well, don’t take this the wrong way, but how come Tristian suddenly asked you out?” she asked, curiosity getting the better of her in the end.

An odd kind of a smile settled on Paris’ lips, almost bashful and a little proud of herself. Rory couldn’t blame her for that, after all, Paris had had a crush on Tristan for as long as they had known each other, and from what Madeline and Louise said, a good amount of time before that too.

“Well, apparently I was seen out with Jess that night we went for pizza,” she explained. “It wasn’t a date, you know that, but clearly the rumour went around that it was. Tristan got to hear about it. It’s not like he’s so stupid he doesn’t know I’ve been in love with him since the fifth grade so... I guess he didn’t like the idea of some other guy taking what might be his?” she shrugged, colouring at her own suggestion. “Plus Jess told me how he was the one who popped Tristan in the nose at the dance last November. Guys are so petty about other guys scoring too many points over them.”

“Yes, they seem to care a lot about that,” Rory agreed with a giggle. “But honestly, Paris, I’m really happy for you. Personally, the idea of a date with Tristan wouldn’t thrill me, but I know how much you want this.”

“I really do,” her friend admitted. “But like I said, there was never really anything but book talk between me and Jess. I wouldn’t want you to think he cheated on you or anything, he didn’t. I don’t think he was likely to with me even if I asked him to.”

“Oh, Paris, don’t say that,” Rory shook her head. “Jess likes you, I know he does.”

“Maybe,” she agreed. “But it’s you that he loves.”

“Only as friends,” said Rory awkwardly, but Paris immediately disagreed.

“You can keep on saying that, but we both know repeating the same thing over and over doesn’t make it true,” she said definitely. “The way that guy talks about you? It’s so obvious he’s in love, and honestly, even with my limited knowledge on the subject, I’m pretty sure you’re still in love with him too.”

She was gone before Rory could reply and she honestly wasn’t sure what she would have said even if Paris stayed in her seat. Rory couldn’t even explain the odd smile that had risen unbidden to her lips at the realisation she wasn’t the only one still thinking maybe she and Jess had a shot at something more, she just wasn’t sure how to go about getting there after everything. This needed some serious thought.


“Jess!”

Luke grumbled about trip hazards as he picked up a book from too near the apartment door. His nephew turned down his music so he could actually hear what was being said and looked expectantly at Luke for him to repeat.

“Can’t you just pretend to be a civilised person who doesn’t live in a dumpster for three seconds?” his uncle complained, tossing the hardcover onto the table where Jess was doing his homework. “I mean, you have bookshelves. I know this because I put them all up there on the walls,” he gestured to the many and various places where Jess’ book collection was held. “How do they end up on the floor?”

“That’s not my book,” said Jess staring intently at the tome in question with an odd look in his eyes.

Luke opened his mouth to say that it sure as hell wasn’t his either when a thought hit him. It would be Rory’s book, in fact he half-remembered Jess making a big deal about how he wasn’t going out of his way to get it back to her if she wasn’t prepared to come ask him for it. It was after the break up and Luke had never felt so stuck in the middle. Now Jess and Rory were back to being friends, which made his nephew’s wistful looks at The Holy Barbarians all the more strange.

“If it’s Rory’s book, why don’t you try, I don’t know, giving it back to Rory?” he suggested.

Jess sighed.

“Because I didn’t get around to it yet.”

Luke had a feeling there was more to it than that and yet loathed the idea of asking. It was either going to lead to a fight, or a conversation about feelings. Luke would rather spend an hour locked in a room with Taylor and Kirk than either of those things. Still, he couldn’t help himself, he couldn’t just leave Jess to wallow.

“You two are okay again now, right?” he said carefully, busying himself in the safe from which he needed more change.

“We’re friends, yeah,” said Jess vaguely. “But... it’s different.”

“Well, of course it’s different, Jess. You guys were closer for a while...”

“Actually we weren’t,” his nephew replied, causing a frown on Luke’s face until he elaborated. “I mean, we were physically closer, supposedly in a closer relationship, but honestly? We were usually further apart in any real terms. We stopped talking, we stopped... connecting.”

“Connecting,” Luke echoed, wishing he was anywhere but here, wishing more than anything that Lorelai was here actually.

Like a timely angel, a knock of the door was followed by his girlfriend’s appearance. Luke almost felt the need to cry ‘hallelujah’ as he closed up the safe and rushed to greet her.

“Lorelai!” he hugged her so tight the air was completely knocked out of her lungs.

“Hey, missed you too, lover,” she smiled as she hugged him back, trying not to make it too obvious when suddenly he was whispering in her ear about Jess.

“Please, talk to him. It’s getting mushy and I can’t stand it.”

The next second he was kissing Lorelai’s cheek and then rushing out the door. She turned to watch him go and then looked back at Jess who was smirking.

“Wow, he’s just subtle like a flying brick today,” he dead-panned.

“That’s our Luke,” Lorelai agreed as she came over and pulled up a chair. “So, we both know he just bailed because you mentioned the dreaded F word - feelings,” she clarified. “Anything cool Aunt Lorelai can help you with, slugger?” she asked.

Jess smiled some at the nickname. She had a habit of calling him things like that, and he actually kind of liked it. He certainly missed it when he and Rory were keeping their distance and he didn’t see so much of Lorelai either.

“I don’t know,” he shrugged. “Not sure I’m supposed to talk to you about me and Rory. Probably puts you in the worst position ever.”

“Probably,” Lorelai agreed. “But hey, tell me anyway!” she grinned.

He laughed at her usual craziness but was serious again in a second. Jess wasn’t good at talking like this, and though Lorelai made it easier than most, it was still tough to verbalise what he was feeling, especially when these feelings were mostly for Rory.

“Do you think we did the right thing breaking up?” he asked straight out then.

Lorelai bit her lip.

“I think that if you both decided it was best then it probably was,” she said thoughtfully. “Only you and Rory know how you and Rory truly feel,” she shrugged. “But, I will say this, whether you guys are friends, or more, or even less, I am always here for you, Jess,” she promised a hand on his arm. “Unless you actually hurt Rory on purpose, then I’ll kick your ass to the moon, but I highly doubt that would ever happen.”

“I promise you, it never will,” he swore sincerely.

Lorelai nodded because she knew he spoke the truth. She was also pretty sure that Jess and Rory would never be less than what they were now, and it was highly likely they would be more again before long. Still, she wasn’t going to go poking her nose in and complicating matters. She meant what she said, she was there for Jess, as she was there for Rory, but she would not influence things. She and Luke just had to sit back and let this one play out, no matter how long it might take.