Chapter Text
It was just shy of 9 p.m. on a late April night, and Stars Hollow had folded in on itself like a storybook closed for the evening. Porch lights glowed dim and dreamy behind gauzy curtains, windows were latched shut against the cool spring air, and the occasional creak of a screen door or bark of a distant dog was muffled by the rising chorus of crickets. The kind of night where time slowed down just enough to notice it.
Rory Gilmore sat in the passenger seat of her car—her car.
The one Dean had built for her from scraps and late nights, fingertips stained black from engine grease and heart stitched into every bolt. The car he gave her with that happy smile of his, standing beside it like a boy offering her the moon. The car that came with more than a key—it came with his first I love you, said so sincerely it still echoed in the corners of her memory.
And now Jess Mariano was behind the wheel.
His arm was hooked casually out the window, fingers trailing the breeze like he’d always belonged there. Like this seat was made for him, like he fit in her space. He drove one-handed, posture loose, eyes on the dark road like he knew it better than he actually did. The dash light painted his face in soft glows, highlighting the sharp line of his jaw, and the restlessness always buzzing under his skin.
He hadn’t asked to drive. She hadn’t offered.
It just... happened.
They’d left Luke’s after one too many sarcastic jabs about how boring her homework was. He was supposed to be the student, after all. She, the tutor. That was the deal. But Jess had a way of undoing structure with a smirk and well-put lyrics. And when he suggested ice cream instead—something about a late-night craving and her being “way too serious for a Thursday”—she didn’t even fight him on it. She just sighed, gave a half-hearted eye-roll, and tossed him the keys.
He caught them midair, quick reflexes and quicker grin. Like it was the most natural thing in the world. Like this had always been part of the plan.
It wasn’t.
But she let it happen anyway.
And maybe that was the part that scared her. Or thrilled her.
Or both.
She leaned back against the cool glass of the passenger window, pulling the sleeves of her hoodie over her hands. The road beneath them had long since disappeared into gravel and damp leaves. The kind of peace you only got on the back roads—the kind that felt like you were somewhere just outside the map. The kind that made rules feel far away.
So much for being the responsible one, she thought.
She’d wanted this. Wanted to break away, just a little. Bend instead of snap. She found herself doing that a lot lately. Especially with Jess. It wasn’t rebellion exactly. It wasn’t even defiance. It was gravity. Something pulling her in, making her feel like herself and someone entirely different all at once.
And Jess—
He wasn’t asking questions anymore.
He was just driving.
They’d spent the last half-hour just driving around, talking here and there, mostly letting the space fill with half-said thoughts and music. And when he suggested heading back to the diner, she told him to take a left instead. Then another.
Now, they were parked in front of the old, rundown inn. The one with the sagging porch and shuttered windows. The one her mom and Sookie talked about constantly—their dream. Their inn. Well, it wasn’t that yet. Not even close. Just a forgotten building with wildflowers choking the driveway and a name fading off the old sign. But still, Rory knew what it meant.
Jess didn’t. Not really.
She leaned against the passenger-side door, one leg tucked beneath her. The car was cluttered with her usual chaos—scattered tapes, a crumpled takeout bag, and a paperback with its cover long gone, pages soft and dog-eared from being reread too many times.
The CD she’d brought played low through the speakers—Wilco, Yankee Hotel Foxtrot. She’d made him put it on the second they pulled up to the inn. “Kamera is the best one,” she’d said, half daring him to disagree.
He didn’t. He just turned the volume up a notch and settled deeper into his seat, like the moment had nothing to prove.
The air in the car felt warm and close, tinged with the leftover smell of fries and the faint, clean scent of spring just beyond the opened window. Every so often, a gust of cool air slipped in, brushing her cheek, a small reminder that the world outside still existed.
Her hands were a little damp. She noticed that. Not from cold. Obviously. From nerves, maybe. From the way her stomach kept flipping over itself every time she remembered exactly where she was, who she was with, and what this night might look like from the outside.
Dean would lose it if he knew where she was—and who she was with. She was sure of it. Even if she told him nothing happened. That it was just driving, just music, just sitting. He’d still lose it.
And her mom? Rory wasn’t sure. She liked to think Lorelai would be chill about it—cool mom and all—but something about Jess always short-circuited her. And Rory being out this late, alone with him, in the car Dean built for her? Yeah, that would raise an eyebrow. Or both.
For now, she took comfort in the idea that Lorelai still believed her sweet, responsible daughter was at the diner, patiently teaching Jess algebra or figures of speech interpretation. Not out here doing what could, from a certain angle, look like full-blown rebellious car-sitting.
You know—the gateway act that leads straight to leather jackets, motorcycle rides, and possibly running away to join a punk band in Jersey.
At least in Lorelai’s mind.
She really hoped her mom wouldn’t get some sudden burst of late-night worry and decide to swing by Luke’s to check on her. A random panic drive, Lorelai-style.
And she really hoped that, if Dean had called the house, her mother either didn’t answer—or had the good sense to lie and say Rory was with Lane.
The music played on.
They’d been quiet for a while. It wasn’t weird. It wasn’t tense. It just... worked.
Then Jess broke it.
“So…” he said, voice low like he didn’t want to ruin whatever this was.
She turned slightly, a small smile on her lips.
He didn’t say anything for a second, and she caught herself getting lost in his dark eyes. It almost looked like he was doing the same—caught in hers.
She pushed the thought away just as he cleared his throat, and spoke.
He nodded toward the building. “Whose place is this? Looks like the set of a horror movie. Like one of those haunted boarding schools where a ghost girl stares at you from the top floor.”
Rory huffed a laugh. “It’s not haunted. Probably.”
He looked at her, amused.
“It’s an old inn,” she explained. “My mom and Sookie want to buy it someday. Fix it up. Make it their own.”
Jess squinted at it through the windshield. “Seriously?”
“Yeah. It’s their dream.”
He was silent for a second. “Huh.”
“That’s it? Just ‘huh’?”
“I mean, it’s... big. Falling apart. Feels like a lot of work.”
Rory smiled, feeling a mix of pride and protectiveness for her mom. “Yeah, well. That’s kind of their thing. I know they'll make it happen.”
Jess tapped a rhythm on the steering wheel. “You ever think about helping them do it?”
She looked at him. “What?”
“You know. After school. Instead of heading off to Harvard and becoming a journalist-slash-Nobel prize winner-slash-future president.”
Rory turned back toward the inn, laughing a little at the exaggeration, but surprised by how much the question actually landed.
“I want to go to school. To college,” she said honestly. “Sometimes it feels like... everything’s already decided. Like the plan is locked in. I’ve been chasing this since—I don’t even know when.”
Jess gave a small shrug. “Hey, that’s cool too. Just… plans can go sideways. Doesn’t hurt to be open to other possibilities.”
She didn’t answer right away. The music was still on—a little melancholy. Jess kept tapping lightly on the steering wheel, eyes flicking toward her now and then, like he was waiting for her to say more.
“I know that,” she said eventually, her voice a little smaller. Her insecurity crept in again—like earlier, when he’d casually mentioned the rough edges of being a foreign correspondent and it caught her off guard.
He seemed to notice. “I’m not saying you can’t do it. You absolutely can,” he said. “Just... you know, it’s kind of fun sometimes to let life take you somewhere you didn’t expect.”
Rory gave him a smile, eyes questioning. “Like you with this town.”
Jess’s eyes flashed with something—maybe sadness. She didn’t want to press.
But then... part of her did.
So, in the spirit of the night, she asked.
“Why did you come here? To Stars Hollow?” Rory said, careful with the words.
“You know why. My mom made me,” Jess replied, not meeting her eyes. His gaze stayed fixed on the abandoned inn.
Another song had started—maybe the fourth since they’d pulled up—by the time Rory spoke again.
“It’s just… you don’t seem like someone who would do something unless you wanted to.”
Jess let out a small, bitter laugh. “Well, I’m still seventeen, she kicked me out, and I really didn’t want to spend my nights running around East New York.” He paused, then added with dry humor, “I may look tough, but I do like my beauty sleep... and not getting stabbed.”
He said it with a glance at her, a small curve tugging at the corners of his lips, but there was something tired in his eyes—like he was telling her not to push it any further.
She didn’t.
Except for one last question.
“Did something happen? Did you like… skip school or something?”
Jess blinked at her then, his expression unreadable for a moment, like he was trying to decide which version of himself to offer. Then he settled on one: he smiled that crooked smile—and started laughing.
Softly.
And then—
Loudly.
Rory might have been offended if his laugh didn’t sound so nice to her ears.
“What?” she said, chuckling a little herself. “What?”
She said it again, mid-laugh, when he finally stopped, still wearing that infuriating smirk.
“Nothing,” he said, still grinning. “You’re such… a good girl.”
He said it teasingly, but something about it made her stomach flip—again.
Rory let out another small laugh, a little uncomfortable. “I’m not,” she replied.
Then quieter, “Not always.”
She picked at her jeans, suddenly hyper-aware of how close they were in the car. How dark it was. How quiet.
Jess’s eyes sparked with a twinkle of mischief. “No?”
She shook her head, eyes fixed on the dashboard. “People just… think that. They see what they want.”
A pause followed—not heavy, just honest.
Jess spoke again, softer this time. “I was just joking, you know. There's nothing wrong with being... good. And I don’t think you’re just one thing.”
Rory looked at him—really looked at him—and this time, she didn’t look away.
Which was strange.
Because normally, she would.
That’s what she did with Jess. She deflected, she smiled, she escaped into sarcasm or books or excuses. She kept the rules in place. The lines clear.
But right now, in the dark of her car, parked in front of the falling-apart inn her mom dreamed about saving, those rules felt farther away than usual.
I don’t think you’re just one thing.
He’d said it so simply, like it wasn’t loaded, like it didn’t stir something in her she couldn’t quite explain.
She wanted to believe him.
That she didn’t have to be the smart one, the good one, the careful one all the time. That someone could see past all of that and still want to sit with her. That she could break the pattern without breaking herself.
But wanting something and knowing what to do with it were two very different things.
She let her eyes drop for a second, just to breathe.
He was still watching her. Not pushing. Just... there.
And maybe that was what made her feel safest and most unsure at the exact same time.
Suddenly, she felt a rush of anxiety, tangled up with something bold and unfamiliar.
She looked at him again and moved slightly closer on the seat. Jess seemed to lean in, too—like he was listening in on a secret.
For a second, Rory thought about kissing him.
Really thought about it.
She wondered what it would feel like to kiss him now. It would be reckless. Rule-breaking. Exactly the kind of thing she never let herself do.
She imagined letting that intrusive thought win for once.
Not thinking about what people expected of her.
Not thinking about what Dean would say. Or what Lane would guess. Or what her mother believed Jess was.
She had been the one who wanted to drive around.
She had been the one who told him to come here.
And if anything was about to happen, it would be her choice.
But instead of kissing him—something that would’ve felt absolutely out-of-her-mind, full-on crazy—she did something almost as crazy.
She reached for his hand.
Her fingers touched his first. Then she pressed her lips together and let the rest of her hand fall into his.
Jess didn’t flinch. He slowly interlaced their fingers together, like it was something he’d been waiting to do.
Rory didn’t look at him.
She just looked at their hands—intertwined. Watched how her fingers played with his. How his moved with hers. It was such a small thing. Mundane, even. But it felt so daring her heart didn’t know what to do with itself.
They stayed like this for a minute or two.
Or maybe twenty. She wasn’t sure anymore.
At some point—she didn’t notice when—Jess tilted a little until his forehead rested against the top of her head.
His thumb was moving now, tracing slow, even circles over the back of her hand.
The warmth of his skin settled into her hair, and her heartbeat kicked up in seconds.
She could hear him swallowing. Hard. Repeatedly. Like someone trying to keep their nerves in check.
She didn’t dare look up. Didn’t know what she’d find in his eyes if she did.
And she wasn’t sure she could trust herself with what she might do.
So, they stayed like that.
At some point, she felt Jess’s forehead move, and then it was his mouth resting against the top of her head.
He didn’t kiss her. Just lingered there, still, the heat of his breath moving through her hair, hot against her scalp.
After a few seconds, he shifted again, and his cheek replaced his mouth—just as warm, just as close.
For a moment, she was sure this was the most romantic, anticipation-filled moment of her life.
And then—courage struck.
Just as she began to move—ready to lift her head, to look at him—
A loud honk shattered the moment.
They jolted. Rory’s head hit Jess’s in a painful thump. They both groaned, scrambling apart in shock.
Headlights were flashing behind them.
Rory couldn’t make out whose car it was—and, frankly, she didn’t want to.
Jess, ever the one who somehow knew how to handle this kind of thing, recovered fast. He pulled his hand away, started the car, and drove.
Drove away from the inn.
Away from the headlights.
Away from the moment.
--
He drove them back to Luke’s.
This time, they didn’t talk. The silence sat thick between them—uncomfortable now, heavy in a way it hadn’t been before. Rory felt both sweaty and cold, her heart still thudding dully against her ribs. Guilt crept in, wrapping around her chest and tugging at every unfinished thought she was trying not to have.
As Jess parked the car outside the diner, he got out without a word. Rory followed suit, quickly sliding into the driver’s seat this time—almost like reclaiming something.
Jess glanced at her. “Huh… your books are inside.”
“Oh,” Rory said, taken aback. “Right. Of course. My books. Silly me.”
She hurried after him, and the second the door closed behind her, the words started spilling out—too fast, too many.
“I mean, those headlights were probably just someone from town, right? Like, Mrs. Cassini out late because her cat ran off again, or Taylor doing a surprise night patrol for the historical society or something. Or maybe it was Kirk? He probably has a flashlight collection and now he’s testing headlights too. Who knows with Kirk.”
She laughed. A little too loud. Way too forced.
“I mean, what are the odds it was anyone we know who would actually care what we were doing out there? Not that we were doing anything, because we weren’t. Obviously. Not that it would matter if we were, because it’s not illegal to sit in a parked car and listen to music. People do it all the time. It’s like… a Stars Hollow tradition. You know, like corn festivals and accidentally falling asleep during town meetings.”
She forced a shrug, reaching for her books without meeting his eyes.
“Anyway. Hum. Thanks for the…uh… ride.”
She turned quickly, already halfway to the door when she heard him.
“Hey.”
She stopped. Hesitated. Then looked back.
Jess was standing by the counter, hands in his pockets.
“It’s fine,” he said. “Nothing… nothing happened.”
Rory swallowed, nodding faintly. “Right. Yeah. I know.”
But her fingers clenched tighter around her books.
Jess looked at her for a second, like he wanted to say more—but didn't. Or couldn't.
Rory gave a small smile, one of those half-hearted ones she used when she didn’t know what else to do. “Okay. See you.”
And then she left. Quickly. Before the warmth in her cheeks gave her away. Before she changed her mind and told him that was a lie.
Because something had happened.
Even if neither of them knew what the hell it was.
--
Rory drove back to her house, the road barely registering as her thoughts spun out of control.
What did I just do?
Why did she touch his hand? Why did she do that?
Her fingers still remembered it—how warm his were, how natural it had felt, and how completely, utterly insane the whole thing was.
Was she sick?
That had to be it. Some kind of momentary lapse in judgment brought on by teenage hormones and Wilco and too much silence. Maybe low blood sugar. Maybe brain fog. Maybe temporary insanity.
She hadn’t kissed him.
But she’d wanted to. That was the part she couldn’t stop circling back to.
And she couldn’t even blame Jess for any of it.
He hadn’t made a move.
He hadn’t pushed anything.
He just sat there.
It had been her. Reaching for his hand like some kind of maniac.
She’d done that. On purpose. Without thinking. Or worse—because she was thinking. Because some part of her had wanted to break the rules.
Her heart thudded louder than the engine.
But Jess—he didn’t pull away.
His fingers had laced through hers.
And then there was the moment she didn’t want to think about too much.
The way his mouth had rested against her head. Not a kiss. But not nothing.
She could still feel it. The way her breath caught when it happened.
One thing she knew for sure: friends—or whatever they were—didn’t act like that.
And tutors definitely weren’t supposed to behave that way with their students.
By the time she turned onto her street, the moment already felt like something that existed in another timeline. But her hands still tingled. And her brain wouldn't shut up.
She made her way to the front door, trying to be as quiet as possible—slow, stealthy.
Her goal: avoid her mother.
But of course, the universe had other plans.
The second she closed the door behind her, gently, quietly, barely even a click—
“Oh, Rory, great!” Lorelai’s voice shot out from the kitchen, making Rory jump at least two feet into the air. “Tell me, was it the China Ball, the China Doll, or the China Wall that had the really good shrimp balls?”
Rory blinked, thrown. “Uh… I think it was the China Doll?”
She followed the voice into the kitchen, still a little rattled.
“Okay, great, these can go.” Lorelai held up a takeout menu, already mid-declutter. “You’ll be so proud of me—I’m finally organizing the takeout drawer. I’m weeding out all the duds and putting happy face stickers on the dishes that have been huge successes. It’s like a sticker chart, but for food commitment.”
Rory gave a tired smile, only half-present.
Lorelai narrowed her eyes. “How was it?”
Rory loosened slightly, adjusting her bag on her shoulder. “Fine. I’m just… really beat.”
“You look a little worn out,” Lorelai said, her tone casual, but her eyes scanning her daughter’s face.
Rory shrugged, walking toward her room. “Long night. Brain is officially mush.”
Lorelai followed. “Jess wasn’t too hard on you?”
Rory dropped her bag by her desk. “Uh… no. No. He’s actually really smart. I don’t know why he has such a hard time in school.”
Lorelai let out a half-laugh. “I think the not-caring-about-anything might have something to do with it.”
Rory hesitated. “He cares about things.”
Lorelai cocked her head. “Oh yeah? Like what?”
Rory sat on the edge of her bed, suddenly hyper-aware of how weird this conversation felt. Especially after what had happened not even an hour earlier.
“Well… he loves to read. He’s obsessed with music.” She paused, then added quickly, “Anyway, I’m tired, Mom. I need to sleep.”
Lorelai, who absolutely knew she was dodging something, chose to let it slide—for now. “Of course, Sweets. You’ve got the brains and the looks, let’s keep it that way.”
She gave Rory a kiss on the forehead and backed out of the room. “Sleep well.”
Rory murmured a “Goodnight,” and closed the door behind her mom.
She changed into her pajamas and sank into her bed, but the weight of the evening pressed in. Her body was still, but her mind wouldn’t stop. The softness of Jess’s hand. The quiet of the car. That nearly-almost-maybe kiss that hadn’t happened but somehow still lived under her skin.
She tossed.
Turned.
Stared at the ceiling.
And finally, when sleep did come, it arrived in flashes—half-formed dreams full of headlights, warm skin, and the kind of rebellious teenage feelings that didn’t fit neatly into boxes labeled good girl.
--
The next few days, Rory dreaded seeing Jess.
She’d barely caught glimpses of him since the moment in the car, and she was doing an excellent job of avoiding him entirely. She buried herself in schoolwork, suddenly became very enthusiastic about early mornings, and ducked any Lorelai plans involving Luke’s with vague excuses about studying or needing to reorganize her books by genre.
But by Saturday morning, her excuses had run out.
And Lorelai was not having it.
“I need coffee in my system within the next ten minutes or I’m going to start seeing visions,” her mom announced as they made their way toward the diner. “And not the cool, spiritual peyote-in-the-desert kind. The bad kind. Like Taylor in bike shorts.”
Rory forced a smile, heart thudding louder with each step. As they walked in and picked their usual table, her eyes darted toward the counter.
No Jess.
A small wave of disappointment hit her before she could stop it. Which was ridiculous.
But then, of course—he appeared. Emerging from the kitchen with a plate of oatmeal buried under what looked like a fruit stand explosion, heading toward Babette.
“Whoo, that’s a whole orchard on a bowl!” Babette cackled. “If I don’t get my vitamins now, Morey says I turn feral by noon! …Although now that I’ve got my vitamins,” she added with a wink, “I might just go feral in a whole different way.”
Miss Patty, perched nearby, let out a delighted gasp. “People forget us mature women are in the peak of our lives!”
The two of them fell into knowing laughter.
Jess visibly shuddered at the thought.
Clearly not into it.
He handed her the plate without a word, turned, and caught Rory’s eyes—just for a second.
Rory immediately looked away.
Lorelai caught the whole exchange, her gaze sharpening just a bit.
Jess walked over. “Hey,” he said casually.
Rory hesitated. “Hey.”
Lorelai glanced between them, before speaking. “Hey Jess.”
A beat of awkward silence.
“Can we get two coffees? Or, if you’ve got it in stock, one I.V. drip for me.”
Jess, ever unbothered, deadpanned, “Out of I.V.s. Backordered.”
“Of course they are,” Lorelai sighed. “Two big mugs then, preferably strong enough to give us the jitters.”
Jess gave a small nod and disappeared behind the counter.
He returned a minute later, setting their mugs down with his usual neutral expression. He didn’t say anything, and Rory barely looked up.
“Thanks,” she mumbled, her voice thin.
Jess walked off to clean a table, clearly sensing the awkward fog clouding the table.
As soon as he was out of earshot, Lorelai turned to Rory, lifting her coffee mug like a mic.
“What the hell was that?”
“What was what?” Rory replied, playing dumb with the grace of a brick.
Lorelai gave her the most dramatic slow blink ever. “You mean the painfully loaded ‘hey’? The coffee cup tension? The ‘I’m-going-to-stare-into-my-soul-through-my-coffee’ silence?”
Rory sighed. “Mom…”
“Did something happen? Was there a weird tutoring moment? Did he quote Kerouac too aggressively?”
“No. Nothing. It was fine,” Rory lied, sipping her coffee like it could erase the night from her bloodstream.
“Uh-huh,” Lorelai said. “Because your nothing has a very specific face, and you’re wearing it right now.”
Rory stayed quiet, pretending to focus on the chalkboard specials like the meaning of life was hidden somewhere between “Banana Pancakes” and “Special Omelette.”
Lorelai leaned in, lowering her voice like a spy with a top-secret mission. “Okay, if you’re not going to tell me now, that’s fine. But just know—this coffee has given me superpowers. I will find out.”
Rory sighed, fiddling with her napkin. She wasn’t ready to tell the truth, but maybe a little something would help her mom back off.
“Nothing happened,” she said. “It’s just… I don’t know. We went out to get ice cream. I’m sorry I didn’t tell you.” She added, half-lying, “He’s probably being awkward because he thinks you’re mad at him for it. But I didn’t tell you. It was my idea. That’s it.”
Lorelai tilted her head, a trace of hurt passing through her features—subtle but there. Her kid didn’t tell her. That always stung, even if she tried to act cool about it.
“Babe,” she said softly. “I mean, it’s not that big a deal. But… you’ve got to be careful, okay? You have a boyfriend who loves you. This is a small town. People talk. Especially Taylor, who I’m convinced has a gossip newsletter we don’t know about.”
Rory groaned. “Oh my god, is this the 1950s? We’re friends. Friendly. It was just a break from studying. I even felt bad not telling you. I swear, sometimes I feel like I can’t even do something spontaneous without everyone dissecting it like I’ve gone completely off plan.”
Lorelai blinked at that. It hit a little deeper than she expected.
“Hon,” she replied. “I’m sorry you feel that way. But that’s not what this is. I’m not saying you can’t make your own choices. I want you to. I trust you. It’s just… Jess is—he’s a little more... chaos-in-a-leather-jacket than you are. You might want to be aware of that. That’s all I’m saying. You’re seventeen. Decisions are part of the deal, but sometimes they come with consequences. Not because you’re bad or doing something wrong. Just because they’re complicated.”
Rory threw her hands up a little. “See? I’m literally saying we went for ice cream, and you’re reacting like I went to a Girls Gone Wild party in Cabo or something.”
Lorelai let out a laugh before she could stop herself.
“Mom!” Rory snapped, scandalized.
“Sorry! Sorry. The visual just hit me—bikinis, beads, someone shouting ‘Spring Break!’ And honestly, Mommy would not laugh if that were the case.” She paused, then softened. “But you’re right. I’m overreacting. Ice cream is way too tame for me to act like… well, my mother.”
Lorelai winced at the thought.
Rory exhaled, shoulders relaxing just a little.
Still, the guilt lingered. Not from what happened. From not saying what really did.
Lorelai took another sip of her coffee, eyes still on Rory, but her voice was lighter this time. Almost casual.
“Just—one last thing,” she said, setting the mug down. “And I swear I’m not trying to be that mom.”
Rory raised an eyebrow, wary. “That mom?”
“You know,” Lorelai said. “The ‘I’ve-seen-things-and-I-read-between-the-lines-and-I-make-jokes-so-I-can-say-serious-stuff-without-being-serious’ kind.”
Rory gave her a look. “You are that mom.”
“Exactly,” Lorelai said, unbothered. “So. Jess.”
Rory stiffened just a little. Lorelai clocked it but didn’t push.
“He’s got that whole… complicated vibe. Looks like he reads poetry but also might steal your car stereo.”
Rory made a face. “He’s not—”
“I’m not judging,” Lorelai cut in. “I just think… some people come with more layers than they let on. They’ve got a whole story behind them, and not all of it’s their fault. I know he’s still a kid, too… but that doesn’t mean he’s not already carrying stuff. And that makes him—complicated.”
She paused, giving Rory a look that was more curious than critical.
“Complicated can be fun. Or confusing. Or both. Just depends on the day. That’s not always easy to deal with.”
She smiled, warm but knowing.
“Anyway. I’ll shut up now. Pancakes?”
Rory paused, nodded. “Yeah. Pancakes.”
She stirred her coffee absentmindedly, the steam curling up between them. Lorelai didn’t say anything else, just flagged for Luke with a half-salute that somehow translated to “our usual, please, and make it snappy.”
Across the diner, Jess was wiping down a table, pretending not to notice them. Pretending too well.
Rory glanced at him, just for a second.
Complicated.
Yeah. That felt about right.
She looked back at her mom, who was now dramatically pretending to collapse from hunger.
“Death by carb delay,” Lorelai muttered. “You’ll tell my story, won’t you?”
Rory smiled, just barely. “I’ll make it sound tragic. And mildly heroic.”
“Good girl,” Lorelai said, then turned toward the coffee like it was the only stable thing in her life.
And Rory—she let the silence hang there a little longer this time.
She was just thinking.
Really thinking.
About Jess. About what her mom had said. About what she hadn’t.
She let the thoughts drift in.
Then, let them go.
By the time their food arrived, she eased back into her seat, letting herself be pulled into Lorelai’s current rant-slash-update about Margie, her grandfather’s longtime secretary, who had shockingly decided not to join Richard in his shiny new insurance venture.
“I mean, the betrayal, Rory,” Lorelai said, piling syrup onto her pancakes like it owed her money. “She’s worked for him since forever. Margie knows his coffee order. Margie knows which pen he’ll throw across the room when someone uses the word 'synergy.'”
Rory smiled. “Maybe she’s just… done. Wants to live her life.”
“Oh no, no. Margie lives for file cabinets and fax machines. This is a statement. A grand act of rebellion. Margie is basically the Che Guevara of executive assistants.”
Rory laughed, the sound easing out of her more easily than she expected.
She still felt the echo of everything, stealing glances here and there at Jess—reminding herself of the hand-holding that somehow felt louder than a kiss.
But for now, she let it settle in the back of her mind.
Right now, it was pancakes, and her mom, and Margie’s tiny revolution.
--
That evening, Rory was set to meet Dean at his house for dinner with his family.
He greeted her at the door with his usual big smile and an arm already reaching for a hug.
“Hey,” he said, holding her a little longer than she expected.
“Hi,” she replied, letting herself sink into the familiarity of it. “How was your grandma’s?”
Dean pulled back just enough to walk her inside. “Good. She made that pie she always makes. The crust was kind of dry, but everyone pretended it wasn’t. So… classic family visit.”
Rory smiled politely, toeing off her shoes. “Well, that’s the official job of a grandchild—lie about baked goods.”
Dinner was loud, and full of midwestern family charm. His mom was kind, his dad was polite, and Clara—insisted on talking about Lizzie McGuire for what felt like twenty straight minutes.
“I just don’t get why Kate is always so mean to her,” Clara said between bites of roast. “Like, she literally never does anything.”
Rory nodded along, doing her best to keep up. “Yeah, it’s...a lot of drama.”
After the meal, the three of them headed downstairs to the basement. Dean had already rented Planet of the Apes on video earlier that day. Naturally.
“I figured something fun, a little action,” he said, settling onto the couch with a grin. “Classic Saturday night.”
Rory didn’t protest. Her guilt made the decision for her. She was tired of making waves. Dean was happy, and she wanted to keep it that way.
She sat beside him, while Clara took the other end of the couch, still talking about how Miranda’s outfits were underrated.
About thirty minutes in, Clara got up to use the bathroom.
The second she disappeared up the stairs, Dean leaned toward Rory, sliding an arm behind her and kissing her.
It was familiar. A little pressing. Eager.
Rory kissed him back, out of habit more than anything.
But after a few seconds, she pulled away, reaching for her cola with a cough.
“Sorry,” she said quickly. “I think I ate too many of your mom’s garlic potatoes. My breath probably smells like a vampire’s nightmare.”
Dean laughed, that big, easy laugh of his, brushing it off.
“It’s fine. You’re fine. I like garlic,” he said, leaning in again.
But Rory moved again, pretending to adjust the blanket on her lap, giving herself a bit of space.
She smiled, tried to make it feel real.
But something felt off with her. Not wrong. Just… off.
Dean went back to the movie, his arm still draped over the back of the couch, fingers brushing her shoulder.
Rory stared at the screen, not really seeing it.
Not really seeing anything at all.
After the movie, Dean walked her home. The air had that perfect kind of early-May chill—cool enough to wake you up, but not cold enough to chase you inside.
They reached her porch, the familiar glow of the porch light casting shadows over their faces. Dean leaned in, and Rory let herself go with it, meeting him in a kiss—a lingering one, a little more deliberate than usual.
It wasn’t that Dean wasn’t a good kisser. He was. She liked kissing him.
She just didn’t feel like kissing him right now.
But she did it anyway.
Maybe to prove something. Maybe to fix something she couldn’t quite name.
Maybe because her thoughts kept going back to Jess.
To the car Dean built for her.
To the way she’d reached out in the dark and held Jess’s hand.
Like it meant something.
Like it crossed a line.
She felt like such a… scarlet.
Scarlet A. Scarlet Rory. Scarlet with a side of guilt and a full serving of confusion.
She pushed the thought away.
This was Dean. Her boyfriend. He loved her. Her mom loved him. He was safe. She was supposed to feel good.
Dean pressed closer into the kiss, and Rory let him for a moment longer—until it felt like too much. Like too much pretending.
She pulled back, gently placing her hand on his chest.
“My mom’s inside,” she said, using it as an excuse.
Dean nodded. “Of course,” he said kindly.
He smiled, giving her one last peck on the lips. “Good night, Rory.”
“Night,” she murmured.
“Call me,” he added, already stepping off the porch.
Rory stood there for a second, watching him go. Then she let herself inside, closing the door behind her with a long exhale, and told herself it was just another night. Just like any other.
--
A few days later, Rory walked through the front door after school, her backpack sliding off her shoulder and landing with a soft thud near the stairs.
It had been one of those slow, drifting weeks—normal on the outside, but just a little off. She hadn’t really talked to Jess. Not beyond a quiet, barely-there “hey” at Luke’s when she was with her mom. No real eye contact. No conversation.
And so far, she'd done an excellent job of pretending nothing had happened between the two of them. She was Dean’s girlfriend after all, and that was that. She loved him. Case closed.
“Mom?” she called into the quiet house. No answer.
She wandered over to the desk and hit the blinking play button on the answering machine.
“Hey you, it’s me,” Lorelai’s voice crackled through the speaker. “I’m going to be home a little late today—still trying to find Grandpa a Margie. So, order pizza, money’s under the rabbi. Buh-bye.”
Rory smiled and reached under the ceramic rabbi figurine, pulling out a couple of bills. “Still the rabbi,” she muttered to herself.
In the kitchen, she grabbed a soda from the fridge and had just popped the tab when the phone rang. She picked up the cordless, pressing it to her ear.
“I have found my calling,” came Lane’s voice—loud, breathless, and triumphant.
Rory blinked. “What?”
“My future, my path, my destiny, my thing, my scene, my bag,” Lane continued without taking a breath. “I’m talking about the number one item on my cosmic to-do list.”
Rory leaned against the counter, a grin slowly forming. “Which is…?”
“I’m going to be a drummer!” Lane announced, completely serious.
“You’re kidding,” Rory said, stifling a laugh.
“Nope. I walked into that new music store today—I don’t even know why, I just had to. Something was pulling me in, like a force, a sign. And there it was. Red. Shiny. Beautiful. It spoke to me.”
Rory laughed now, fully entertained. “That’s amazing.”
“I know!” Lane practically shouted.
“But how are you going to do this?”
“I don’t know.”
“How are you going to buy a drum set?”
“Still don’t know.”
“And even if you do buy one, where are you going to play it?”
“Absolutely no idea. But I will figure something out. Because I am Keith Moon. I am Neil Peart. I am Rick Allen—with and without the arm—because I am rock and roll, baby!”
Rory barely had time to reply before Lane’s voice continued, “Okay, I have to go. I’ll call you later!”
The line clicked off.
Rory pulled the phone from her ear, staring at it for a second, a smirk lingering on her face.
“Drummer,” she said out loud, shaking her head fondly. “Of course.”
She took another sip of soda, the fizz biting just enough to wake her up a little, and leaned against the counter.
After hanging up the phone with Lane, Rory ordered a pizza—half pepperoni, half three-cheeses—and settled onto the couch in front of the TV. She flipped through channels until she landed on The Golden Girls. A rerun, of course. But it didn’t matter. The familiar rhythm of their voices, the punchlines she already knew by heart—it was comfort TV. Reliable. Safe.
She tucked her legs under her, grabbed a blanket, and let the canned laughter fill the house.
Her mom called once—not long after the pizza arrived. Rory answered with her mouth full.
“I’m going to be even later,” Lorelai said without much fanfare. “No Margie. Apparently, they don’t make them like they used to. And now your grandfather’s spiraling. He’s convinced no one will ever organize his appointments or refill his favorite pen again.”
Rory swallowed. “So… chaos?”
“Full-on. And somehow, it’s my fault. Richard Gilmore has officially decided that I should’ve been training his staff in administrative logistics from birth. Like baby’s first filing cabinet.”
Rory laughed. “Well, you are great at alphabetizing.”
“Tell that to the man currently reading resumes like they’re Russian novels.”
“Good luck.”
“Thanks. Enjoy your pizza.”
Click.
And with that, she was alone again.
Really alone.
It didn’t happen often—not in Stars Hollow, not with her mom around, and certainly not lately. But now, the house was silent. The only sound was the TV playing in the background and the occasional rustle of the pizza box when she reached for another slice.
She liked it, she realized. The stillness. The breathing room.
It gave her space to think. Maybe too much space.
Her mind drifted back to Lane’s phone call. Her best friend, absolutely buzzing with energy, like she’d been struck by lightning in the form of a drumstick. Rory had been caught up in Lane’s excitement, and now, she found herself smiling again at the memory.
Lane had a way of loving things so completely. She dove in headfirst. She felt things.
Rory envied that sometimes.
She wished, just for a moment, that Lane was here beside her on the couch. They could talk about it. About him. About the moment in the car. About what she hadn’t said out loud to anyone yet.
She hadn’t told Lane. She hadn’t told anyone. And she didn’t really know why.
Well—she did.
She was afraid Lane would judge her. Or worse—not judge her, and just give her that knowing look that meant she was thinking all the things Rory was already thinking.
Was it really that bad?
She hadn’t kissed Jess. There was no dramatic, forbidden make-out session in the backseat of the car.
It was just… hands.
Holding hands.
If anything, it was G-rated. Disney-level. They could’ve done it during Saturday morning cartoons and no one would’ve blinked.
And yet.
She still felt the heat of his fingers in hers. Still remembered the weight of his forehead against hers. The way the world had gone so still, like even the stereo had known to quiet down for a second.
That wasn’t nothing.
But did it count as something?
She pulled the blanket tighter around her shoulders, took another bite of pizza, and tried to refocus on her show. But even Dorothy’s perfectly timed eye rolls couldn’t drown out the question echoing in her mind.
And with that, came a knock on the door.
Rory groaned, instinctively lowering the sound of the TV with the remote. “If that’s Kirk trying to sell leftover Arbor Day buttons again, I swear…”
She got up reluctantly, brushing crumbs off her pajama pants as she padded toward the front door.
“It’s too late for door-to-door sales, Kirk. Or Babette, if it’s you—Mom’s margarita mixer still hasn’t recovered from last time, and she’ll know exactly who broke the lid.”
She pulled the door open mid-sentence, already preparing her best neighborly smile-turned-excuse—
But it wasn’t Babette.
Or Kirk.
It was Jess.
He was standing there, hands in the pockets of his jean jacket, shoulders hunched like he was both too cool to be nervous and way too nervous to admit it.
Rory froze. Completely speechless.
Her heart skipped in a way she wasn’t ready for.
Jess didn’t say anything at first. He looked at her like he wasn’t entirely sure she’d open the door. Like maybe he hadn’t fully planned this out past standing there.
“Hey,” he said finally.
Rory blinked once, twice. “Hey.”
She stood in the doorway, suddenly hyper-aware of her fuzzy socks, her pyjama pants, her blanket still draped over one shoulder, and the fact that she had pizza breath.
Jess didn’t seem to notice—or care.
“I was walking back from, uh… to Luke’s,” he said. “Saw the light. But no Jeep. Thought maybe you were up.”
“Oh,” she said, squirming a little. “Yeah. I was just… watching TV. Eating pizza.”
“Big night,” he said, the corner of his mouth twitching into the tiniest hint of a smirk.
She smiled faintly. “Huge.”
A beat passed.
She was about to say something else, something awkward or explanatory, when she caught the light flicker in Babette’s window across the street. The reminder of Stars Hollow’s ever-watchful eyes nudged her into action.
She stepped back.
“You can come in, if you want,” she said quickly.
“I don’t know why I came,” Jess admitted after a second. “I guess I thought… maybe you’d want to talk.”
Rory hesitated.
She did.
But also… she didn’t know how.
“I haven’t told anyone,” she said suddenly, surprising even herself. “About… the car. That night.”
Jess looked at her, something soft flickering across his expression. “Okay.”
Another pause.
The night air curled around them—cool and still—and Rory tightened the blanket around her shoulders again, but not because she was cold.
Jess shifted his weight like he might say something else, then didn’t. He glanced past her toward the light spilling from the living room, then back at her.
Rory cleared her throat.
“Do you… want to come in?” she repeated, quieter this time, yet still very aware of potential curious eyes.
Jess looked at her for a beat, like he was checking to see if she meant it.
“Yeah,” he said quietly. “Sure.”
She stepped back to let him in, closing the door behind him. The sound of the TV continued in the background, laughter filling the room like it belonged to someone else’s life.
Jess stood awkwardly near the entrance for a second, taking in the familiar surroundings—the pile of books on the coffee table, the half-eaten pizza, the blankets Rory had left crumpled on the couch.
“You were really going hard on the solo night,” he said, trying for casual.
Rory gave a half-smile as she sat back down. “Sometimes it’s just me, Blanche, and the pepperoni.”
He hovered for a moment before easing down on the opposite end of the couch, hands still in his hoodie pockets.
Another pause.
It wasn’t heavy. Just… tentative. Like any sudden move might break whatever fragile thing had started to settle.
“I… things are weird now,” Jess said eventually, still not looking at her. “I didn’t… I didn’t mean to make them weird. I wasn't stalking or anything but I just... I wanted to tell you, everything's cool on my end.”
“They’re not weird,” Rory replied a little too quickly.
Jess lifted a brow, finally glancing over at her.
“Okay, they’re a little weird,” she admitted. “For what it’s worth… it was my fault.”
Jess shrugged. “I didn’t exactly protest.”
Rory looked at him, trying to decide if that made her feel better or worse.
She didn’t come up with an answer.
Outside, the town was dark. The light in Babette’s window had gone out.
Inside, Dorothy delivered a punchline Rory didn’t hear.
The silence stretched—until Jess’s eyes drifted to the coffee table. He leaned forward, brushing past the pizza box and picking up one of the paperbacks near the edge.
He held it up between two fingers.
“Girl, Interrupted, huh?”
Rory gave a slow blink. “Yeah. For…uh, fun.”
Jess laughed a little at that. He flipped the cover closed with a finger. “I liked it.”
She stared at him again. “Seriously?”
Jess smirked. “Yes, seriously. I am capable of relating to complex women characters. I don’t spend all my time lurking in corners quoting Catch-22.”
A small smile tugged at Rory’s lips. “Okay, but that’s kind of your brand.”
“Not exclusively,” he said, tapping the cover of the book. “It’s good. Honest. Raw. But not trying too hard. ‘I was never really crazy, I was just a little depressed.’ Like that’s supposed to be a better diagnosis.”
Rory gave him a sideways look. “You remember exact quotes?”
Jess shrugged. “Hey, some things stick. Plus, I saw the movie not too long ago so, that helps.”
She didn’t know what to say to that. Because something in his voice made her wonder what else had stuck. And how much he’d seen in that book that felt… maybe a little too familiar.
She took the book back from him, fingers brushing briefly. He didn’t pull away. Neither did she.
And just like that, they were closer again.
The TV was still playing, but they’d long since stopped pretending to watch it. Jess sat with his elbow hooked over the back of the couch, his knee nearly touching hers. Time seemed to slow again, less like a pause and more like a question.
Rory’s fingers fiddled with the spine of the book in her lap.
She didn’t want to feel what she was feeling. But she did.
She looked at him out of the corner of her eye.
His hair was doing that messy thing it always did when he didn’t bother to fix it. He was leaning back a little, looking like he was caught in some thought. His eyes weren’t on her, but she could still feel something focused about him—like he was thinking too hard about not thinking too hard.
She didn’t get it.
Why it still felt like this—charged, sharp, hard to shake. Why, even now, doing absolutely nothing, he was still managing to get under her skin.
Her heart beat louder in her ears than the canned laughter from the TV.
She could hear Lorelai’s voice in the back of her head, reminding her of everything she was.
Everything she was supposed to be.
Dean’s face floated to the front of her mind. Smiling. So nice. So good.
And still, her hand moved.
Almost like it had a mind of its own.
Once again.
She reached over, and let her fingers brush Jess’s again.
He looked down—but didn’t say anything.
He just turned his hand over.
And when she slid hers into his, he laced their fingers together without a word.
Rory didn’t breathe. She just stared down at their hands.
It wasn’t new.
But it still felt like breaking one big rule.
One time, okay. Twice... not so okay.
Her fingers played with his, like they were learning a language in secret.
Her throat was tight. Her eyes cloudy.
She wasn’t sure if it was bravery, insanity or betrayal that made her do it.
But she couldn’t bring herself to let go.
Not yet.
For a while, they just sat like that. The screen flickered on, ignored.
Jess’s thumb brushed lightly over the side of her hand. He stayed silent.
And then, almost too quietly to count as speaking, she said, “I don’t know why I’m like this.”
Jess didn’t say anything right away. His hand never stopped moving against hers.
“Like what?” he asked, his voice a whisper, almost matching hers.
Rory paused, eyes still on their hands.
“Like… doing this. Wanting this,” she murmured. “It doesn’t feel like me.”
Jess took a few seconds to respond. When he finally spoke, it was faint, maybe even a little confused.
“There’s nothing wrong with doing this, Rory.”
Rory swallowed. “It just… it’s wrong. I’m with… Dean. It isn’t who I’m supposed to be.”
That landed in the air—soft, but loud in its own way.
Jess didn’t pull away, though.
He just looked at her then.
And said, barely above a murmur, “Yeah. But maybe it just means something’s not right.”
Rory felt like looking away.
She wanted to look away.
But her blue eyes stayed locked on him, caught somewhere between guilt and wanting.
Jess registered something in her face—something he didn’t ask about—and slowly took their hands, still loosely tangled, and placed hers back in her lap, like he was returning something he had no right to keep.
“I can go,” he said.
Then, after a pause: “I should go.”
He gave a small smile, like he’d already made peace with the fact that he was about to leave.
And as he started to move, preparing to stand—
Rory pounced.
It was like watching herself from outside her body—no thought, no hesitation. Just instinct.
She leaned forward, closing the distance, and kissed him.
Hard.
It wasn’t delicate. It wasn’t careful. It was desperate and clumsy and fierce—like she was afraid he’d disappear if she waited one more second.
Jess froze for half a heartbeat, blindsided.
Then he kissed her back.
His hand moved instinctively, threading into her hair, and that was it—time folded in on itself. The kiss deepened, messy and hungry, like they'd been holding back for weeks. They barely came up for air. She didn’t know where her breath went, only that it didn’t seem to matter.
She had never kissed like this before.
She didn’t know kissing could feel like that. Like being ripped open and stitched back together at the same time.
And then—
Just like the car.
Just like the headlights back at the old inn.
Another pair of headlights sliced across the wall through the living room window.
Lorelai’s Jeep.
It all collapsed in a second.
Jess pulled back, breath shallow, eyes wide.
Rory shot up, holding her mouth like she’d been caught committing a federal crime.
“Crap—my mom,” she gasped, already pulling him by the arm. “Go. Go go go—back door!”
Jess stumbled after her, still catching up, letting her half-push him toward the kitchen.
She opened the back door and turned to face him, heart in her throat, lips still tingling.
“Uh—sorry, I just—”
Jess held up a hand, already backing away onto the porch, his mouth twitching like he wasn’t sure whether to smirk or panic.
“Right. Great night. Very stealthy. Definitely won’t be caught.”
“Jess.”
“I’m going,” he whispered, stepping down. “But for the record—”
He paused, finally looked her in the eye.
And then he kissed her again.
Slower this time.
No rush, no panic—like he didn’t want to leave without this. Without knowing what it felt like when he kissed her.
Rory melted into it.
Her hands gripped the edge of the doorframe, steadying herself, trying to memorize the feel of it—his mouth, his hands, his body.
Then it was over.
He pulled back, and stepped off the porch.
And just like that—he was gone.
Rory stood in the doorway for a second, stunned. Lips still burning. Breath shallow. Her pulse thundered in her ears.
The front door opened.
“Yay, pizza and Golden Girls!” Lorelai’s voice rang out from the living room. “My two favorite food groups!”
Rory spun around and darted down the hall, slipping into the bathroom just in time. She locked the door and leaned against it, catching her breath like she’d just run ten miles.
She stared at herself in the mirror, cheeks flushed, hair messy, lips visibly kissed.
She didn’t look like the version of herself she usually saw. The version everyone else expected.
She wasn’t sure she hated it.
She didn’t plan for tonight to happen.
She didn’t mean to fall into it.
She was supposed to be the good girl.
The dependable one.
The one who followed the rules and told the truth and dated the boy who brought her ice cream and adored her mother.
But tonight?
Tonight, she’d kissed someone who wasn’t her boyfriend.
Twice.
And not because she was confused. Not because she’d been tricked.
Because she’d wanted to.
And that scared her more than anything.
She splashed cold water on her face. Brushed her hair back. Practiced her smile.
By the time she walked back out into the living room, her mom was already halfway through a slice of pizza.
“Hey, bathroom ghost,” Lorelai said. “What took so long?”
Rory grabbed another slice and curled up at the opposite end of the couch.
“We don’t ask a lady such questions,” she replied before taking a bite.
But it wasn’t true.
She wasn’t a lady.
She felt completely on fire.
And completely not like herself.
Or maybe—just maybe—she did.
And for a second, that didn’t feel like the worst thing.