Chapter Text
Jason Todd wasn’t used to nerves.
He’d died, come back, fought crime lords, and stared down monsters without so much as a tremor in his hands. But right now, pacing the living room of his apartment, hands shaking as he tried for the third time to knot his tie, he was sweating bullets.
Because tonight wasn’t just any night.
Tonight, he was going to propose to Penny Parker.
She was in the bedroom humming softly to herself, completely unaware that her boyfriend of was losing his goddamn mind ten feet away. Jason glanced down at the velvet ring box sitting open on the coffee table.
The ring wasn’t flashy — Penny hated anything too extravagant. It was delicate, elegant, and practical enough that she could wear it under her gloves. A silver band inlaid with a faint pattern of webbing, a small emerald nestled in the centre that matched her eyes perfectly.
It had taken him six months to find a jeweller willing to craft something that could survive her lifestyle. Vibranium alloy coating, reinforced edges — hell, Bruce had to pull a few strings at WayneTech just to make sure it wouldn’t shatter if she punched a wall.
Now that he actually had it, Jason wasn’t sure his heart had beaten properly in the last twenty minutes.
“Pull it together,” he muttered to himself, scrubbing a hand down his face. “You’ve stared down Ra’s al Ghul. You can handle asking your girlfriend to marry you.”
A pause.
“Okay, maybe not as easy as I thought.”
The Plan
Jason wasn’t big on grand gestures — too much potential for chaos, especially in Gotham. So, he’d planned something small, quiet, and personal.
A night on the rooftop where they’d first teamed up. Dinner packed in a basket Alfred had “innocently” helped with. Candles, music, the city lights sprawled out below them.
Simple. Private. Perfect.
Except… nothing was going perfectly.
The candles refused to stay lit in the wind. The wine cork broke in half. And when he tried to test the playlist on his phone, it started blasting the Bat-Signal alert tone instead of soft jazz.
Jason froze. “No. No, no, no—” He smacked the phone against his palm. “Why?! How did you even—”
From behind him, Penny’s voice floated down the hall. “Jay? You okay out there?”
“Fine! Totally fine!” He winced at how high his voice cracked. “Just, uh, fighting with technology again.”
Her laugh echoed from the bedroom. “You know, for a guy with a genius girlfriend and five hacker siblings, you’d think you’d have figured out how to use Spotify by now.”
Jason shot the phone a glare. “Traitor.”
The playlist finally switched to the right track — something slow, soft, with piano and strings. He sighed in relief, pocketing the phone and checking the ring one last time.
Tonight had to be perfect. Penny deserved nothing less.
Flashback — When He Knew
Jason hadn’t planned on falling in love again.
Not after everything — the pit, the anger, the broken parts of himself he’d buried under layers of leather and gunpowder. Love felt like a luxury for other people.
Then she dropped out of the sky. Literally.
A red-and-blue blur that crashed through his patrol, webbed up three armed muggers in under ten seconds, and then had the audacity to apologise for “stealing his bust.”
At first, he’d thought she was reckless. Too bright, too hopeful, too good for Gotham.
Then he saw her save a kid by diving headfirst off a collapsing fire escape. He saw her patch up one of his wounds after a particularly rough night, hands gentle, voice steady.
And one night, sitting side by side on a rooftop overlooking Crime Alley, she’d quietly said, “You know… I don’t think Gotham’s hopeless. It’s just tired. Someone’s gotta keep believing in it until it remembers how.”
That was the night he fell in love.
The Rooftop
Penny emerged from the bedroom, wearing one of Jason’s black leather jackets over a soft red sweater and jeans, her hair pulled back, the white streak gleaming under the low light.
“You ready?” she asked, smiling.
Jason’s breath hitched.
He’d seen her fight gods and villains, bleed and laugh and save the world more times than he could count — but this, this quiet version of her, glowing in the evening light, was what killed him.
“Yeah,” he said, voice low. “Let’s go.”
The rooftop looked… decent, all things considered. The candles flickered stubbornly in their jars, the dinner spread laid out neatly on the blanket, and the city skyline stretched endlessly around them.
Penny’s eyes widened as she stepped onto the roof. “Jay… this is beautiful.”
He rubbed the back of his neck, sheepish. “Alfred helped.”
“That explains why it doesn’t involve bullets or biker bars.”
He laughed, pulling her closer. “You wound me, sweetheart.”
They ate. Talked. Laughed. She teased him about nearly burning the toast again that morning; he countered with stories of her mumbling science formulas in her sleep. The conversation flowed easily, like it always did with them.
At one point, Penny leaned back on her elbows, gazing out at the city lights. “You ever think about how far we’ve come?”
Jason followed her gaze. “All the time.”
“Years ago, I didn’t even think I’d make it through winter.” Her voice softened. “Now look at us.”
Jason swallowed hard. Now look at you, he thought.
The woman who’d fallen into a world that wasn’t hers, built a new life, saved his city, and healed him.
If he didn’t do it now, he never would.
The Moment
Jason stood, trying to act casual and failing miserably. His pulse was hammering.
“Hey, uh, I’ve got something for you,” he said.
Penny looked up, curious. “You got me another waffle maker, didn’t you?”
He chuckled nervously. “Not this time.”
He took a deep breath, steadying himself as he reached into his jacket pocket. The small velvet box felt impossibly heavy.
“Jay?” she asked, brow furrowing. “You okay?”
He nodded, throat tight. “Yeah. I just—look, I’ve been trying to figure out how to say this for months. And knowing me, I’ll screw it up if I don’t just—”
He trailed off, then motioned toward the edge of the roof. “Can you, uh… turn around for a sec?”
Penny raised an eyebrow. “What, are you gonna push me or something?”
“Just—trust me, okay?”
She sighed but smiled, turning around to face the skyline. “Fine. But if you push me off, I swear—”
Jason dropped to one knee.
For a heartbeat, the world went silent. The wind caught his jacket, the candles flickered, and his breath fogged faintly in the chill air.
“Okay,” he muttered to himself. “No going back now.”
“Jay?” she asked, glancing over her shoulder. “What are you—”
Her words cut off when she turned fully.
Penny froze.
Jason was kneeling before her, ring box open, his pit-green eyes soft and uncertain in a way she’d never seen before.
The Speech
He took a shaky breath. “You know, Parker… you’ve got this habit of completely wrecking my life.”
Her breath hitched, eyes wide.
“I was fine before you,” he continued, voice trembling slightly. “Not happy, not good, but… fine. I had my rules, my anger, my city. Then you dropped in — this bright, chaotic, brilliant force of nature — and suddenly everything was different.”
He smiled faintly. “You made me laugh again. You made me care again. You taught me that there’s still good in this city, in me, and that no matter how broken something gets, it’s worth trying to fix.”
Penny’s eyes were glassy now, her lips parted, trembling.
Jason held the ring out, voice quiet but sure. “I don’t deserve you, not even close. But I love you, Penelope Parker. Every scar, every shadow, every impossible thing about you. And I don’t ever want to spend another night not knowing you’re mine.”
He smiled softly. “So… what do you say, sweetheart? You gonna make me the luckiest idiot in Gotham?”
For a long moment, she didn’t speak. Just stared at him — eyes wide, hands trembling, breath catching.
Then she let out a half-laugh, half-sob, covering her mouth.
“You absolute idiot,” she whispered, tears spilling over. “Of course I will.”
Jason’s grin broke wide as he slid the ring onto her finger — it fit perfectly. She tackled him a second later, both of them collapsing onto the blanket in a tangle of limbs and laughter.
“You planned this whole thing, didn’t you?” she said between kisses.
“Maybe.”
“And you were nervous?”
“Maybe.”
“You? Jason Todd?”
“Hey,” he protested. “You try proposing to a super-genius multiversal spider woman who could literally bench-press you. See how calm you are.”
She laughed again, pressing her forehead against his. “You’re ridiculous.”
“And you love it.”
“Yeah,” she whispered, smiling through tears. “I really do.”
They stayed there long after the candles burned out, wrapped in each other beneath the stars.
The city stretched endlessly around them — dark, dangerous, alive — and yet, for that brief sliver of time, Gotham felt at peace.
Penny turned her hand, watching the ring glint faintly in the moonlight.
“Hey, Jay?”
“Yeah?”
“You realise this means you’re stuck with me forever, right?”
Jason smiled, kissing her knuckles. “That’s the plan, Pen.”
And under Gotham’s endless sky, the Red Hood and his Spider tied their hearts together — not with webs or vows, but with quiet laughter, whispered promises, and the unshakable certainty that somehow, against all odds, they’d found home in each other.