AN: I know the timeline is a little fishy - Rory is a senior in this story when Jess comes to Stars Hollow, versus a junior - but this chapter has a lot of smushed together canon in it. It's just obviously in a different time, so things like Lorelai's relationships are sped up, and it's not all happening in the same ways :) Wanted to say that as I went. All similarities are credited to the show creators! I did try to change dialogue around to make it more unique to who I've made characters to be.

P.S. Jess is particularly melancholic this chapter. Just be ready for lots of teenage angst and sighing as we tap into the moodiness of his character ~


As the bus turns into his uncle's town, Jess sighs to himself. He watches as the bus driver turns the bend and slows down to pull off on the side of the road. This is his stop, and he knows it, but the rising bile in his throat makes him hold back as others get off before him. He didn't want to be here.

He grips his bag in his hand and busies himself with thoughts of smoking a cigarette as he walks down the steps. He felt like he was going crazy.

Stepping off the bus, he sees Luke standing in front of him. He hadn't seen Luke in a year or two, but his uncle looked exactly the same.

"Jess," Luke says with a smile, nodding at him. Jess sighs and slings his bag over his shoulder.

"Luke."

They stare at each other for a moment before it seems as though Luke gets the hint that Jess doesn't want to talk. He's thankful as his uncle gestures ahead of him, motioning for Jess to follow.

"So, how was the ride?" Luke asks as they make their way across town.

So much for Luke getting the hint.

"Like a carnival ride, only better," Jess deadpans, frowning as a group of children in matching outfits dart around them.

"Yeah, well," Luke mumbles, adjusting his hat. They're in front of the diner door now and Luke steps through. Jess considers bolting, but he knows it would be pointless.

Luke shows him around the place and leads him upstairs to his new home. Jess looks around as Luke talks, unimpressed. He had to admit it felt a lot cozier than his own apartment. Jess had a feeling he wouldn't have to worry about finding liquor bottles hidden in random drawers and couch cushions; Luke didn't come off as the partying type. That alone was comforting in all of this crap.

"Alright, so, I'm going to be closing up the diner tonight around ten," he finally hears Luke say. Had he been talking this whole time? Jess dumps his things on the makeshift bed and moves some clothes around.

Jess pulls a book and his long coveted pack of cigarettes out of the mess of things and gestures towards his uncle.

"See you at ten," he chirps before turning on his heel to head out of the door.

"Wait, Jess. You need keys to get in," Luke protests, dangling the keys in his hands.

Jess stops for a second, looking over his shoulder quickly.

"No I don't," he tells Luke before closing the door behind him.

He jogs down the stairs. He pulls back the curtain and sees townspeople looking at him strangely. Jess rolls his eyes before stepping outside of the diner. He looks around.

"This is heell," he mumbles in a low sing-song tone, shoving his book into his back pocket.

People run by him jovially. It looks like something out of a Disney movie and he feels nauseous. This wasn't the life he was used to, and it certainly wasn't the life he ever dreamed of being a part of. He hangs his head, shaking it, as he walks through town.

Jess walks down the street, taking in the small town vibes and old fashioned store fronts. He passes by a small cafe where an older woman smiles, handing a young child a cupcake. His mouth falls open at the sickeningly sweet sight, and Jess knows it's time for that cigarette.

"Shit," he mutters, reaching into his pockets. Of all things to forget.

Jess looks around for somebody who doesn't look like they're related to Marsha Brady. Someone in this crackpot of a town had to have a lighter.

"Hey, you got a light?" Jess asks, trying to wave down a tall boy walking on the sidewalk.

The kid stops and looks at him, cocking his head to the side before shaking it.

"Uh, sorry, no, I don't smoke," he apologizes, keeping an eyebrow raised.

"Of course you don't," Jess groans, rolling his eyes. "Do you know where I can buy one?"

"Are you new in town?" The boy asks with a laugh, taking a step closer. "This is Stars Hollow. You'll be lucky to find matches here."

Jess gives the guy a bored look.

"Goody," Jess scoffs, pulling the cigarette out of the corner of his mouth. "Just what I wanted, a town of hippies."

He watches as something in the boy's eyes shift.

"You won't survive here with an attitude like that," the boy says dismissively, shrugging. "Trust me, I moved here last year and thought it was pretty dumb. Turned out it's not so bad."

"Peter, was it?" Jess asks, holding out a questioning finger.

"What?" The boy asks, giving Jess a confused look.

"Or, no, was it Greg?" Jess feigns consideration, holding a hand up to his chin. "I don't need the Brady Bunch, let's-all-pretend-this-place-is-magical pep talk, so save it, pal."

"Whatever, man. I don't have time for this," the guy shrugs. He looms over Jess for a moment, glaring at him. Jess raises an eyebrow, wondering if it's a new record of how quickly he's pissed somebody off.

"Watch yourself," the kid spits out before stalking off down the sidewalk.

Jess finally allows a smile before remembering that he never got a lighter.

He sighs, shoving the cigarette into his pocket. He knew he didn't need to make any enemies if he wanted this place to work for him. New York City was a lot more anonymous; he could easily fight somebody and then avoid them if he didn't want to see their ugly mug again. But this place was a lot smaller; it looked like it had a total occupancy of twelve people.

Jess purses his lips and lets out a small growl from his throat. He resolves to be nicer to the next person he sees. He could be sociable.

He was determined to prove Liz and Principal Jeffreys wrong.


"Mom, I don't know why you had me take off," Rory complains into the phone, watching as her kitchen turns into a restaurant.

"I told you, so we can make Luke's nephew feel super welcome, the warm fuzzies and all that jazz," Lorelai answers with distraction. She had disappeared an hour ago after Sookie had asked her to pick up some preliminary things for dinner.

"But you made it sound like we were having brunch or something," Rory continues, ducking as Sookie flies by with a pan. "We're not doing anything until dinner, and I could have gone to school so I'm not behind tomorrow."

"We are doing something," her mother insists into the phone. "I am running around frantically trying to find robin's egg blue napkins, because you know, only the best for Luke's nephew, and you are there watching Sookie."

"I could have helped you on your errands," Rory persists.

"And what happened last time Sookie was alone in our kitchen?"

"Fine, point taken."

"I'll be back soon, sweets," Lorelai coos into the phone. "Why don't you work on your social engagement assignment? You're backed up from Sir Grumps-A-Lot being absent the last two weeks, right?"

Rory bites her lip and twirls her hair. She was behind on her logs, but she also didn't want to think about Jess. His absence had been really heavy for her, and she was doing everything to avoid thinking about the fact that he also wouldn't be there for tomorrow's session. It made her sick to her stomach every time she thought about him instead of Dean.

"Yeah… I guess I could. Or work on my paper for the Franklin," she offers as an alternative, upping the happy octave in her tone.

"That's the spirit," her mother chirps into the phone. "Now, tell me, robin's egg blue - what do we think about pink Easter print instead?"

"Bye," Rory laughs.

"Gah, no help," Lorelai sputters into the phone before Rory hangs up her end.

She smiles at Sookie moving about the kitchen. It was warming to see how loved Luke was that her mom, Sookie, and Jackson were going through such great lengths for his nephew. Rory wonders if Luke has any idea.

She begins to wonder what Luke's nephew is like before Sookie grabs her attention.

"Can you run out to the store and get some fresh basil from Doose's, hon?" Sookie asks, using her foot to shut the door to the oven.

Rory raises an eyebrow.

"Isn't Jackson getting you fresh basil?" Rory asks, raising an eyebrow.

Sookie smiles nervously and looks guilty.

"Okay, I just figured that since Dean's school didn't have classes today and you're home, you'd maybe wanna get out of the house to see him since he's working there instead today," she admits with a smile.

"Is this an attempt to get me away from the kitchen?" Rory asks in mock suspicion, pointing an accusatory finger at Sookie.

"No, I swear," Sookie insists, grabbing a ladle. "It's just, your mom said you've been in such a funk lately."

Rory's face drops. She could recall a few times her mom had commented on her mood in the past week.

"I thought seeing Dean might cheer ya up," Sookie continues, smiling apologetically at Rory. She wasn't one to usually meddle.

"Thanks Sookie," Rory says slowly, her heart panging with every mention of her boyfriend.

She feels trapped. If she insists on doing homework, she has to actually do it… which means thinking about Jess or her Franklin paper, or worse, being too distracted by thoughts of Jess to write the Franklin paper. And it would look even worse that she didn't want to see Dean.

She sighs, fixes a smile on her face, and gets up from the table.

"I'll go grab that fresh basil for you," Rory says as happily as she can before turning on her heel and heading out the door to Doose's.

Rory heads down the block in a fog, maneuvering the familiar bends and turns to get to the market. When she finally gets to Doose's, she feels some excitement at the prospect of seeing Dean. This gets her even more excited as she pushes through the doors, wandering the aisles to find him.

"Hey, you," she says with a smile, finally finding Dean by the canned peas.

Dean looks up at her and smiles brightly, standing up to grab Rory for a kiss. She leans in, enjoying the moment, and steps away with a smile on her face again.

"Hey, what are you doing here?" Dean asks, a look of confusion on his face.

"I stayed home today to help mom with this dinner for Luke and his nephew who's coming to visit," she explains, tucking her hair behind her ear. "I thought I'd surprise you - are you surprised?"

"Yeah, I'm surprised," Dean nods, giving Rory another peck on the lips. "Hey, let me go tell Taylor I'm taking my fifteen," he tells her quickly before scurrying off.

It's only a moment before Dean is back and grabbing Rory's hand, walking outside with her to the gazebo in the town centre.

"So how's your day going?" Rory asks, plopping herself down on the steps next to Dean.

"This morning was a little weird, but otherwise, work's been fine," he says with a shrug, his eyebrows knitting together in annoyance for a second.

"Weird?" Rory asks with concern, noting the look on his face.

"Well, it's just, there was this kid I've never really seen around before," Dean explains, waving his hands as he talked. "I tried being friendly but he ended up being a jerk."

Rory scrunches her mouth and gives Dean an empathetic look.

"I'm sorry. Well hey, maybe he was just a moody tourist passing through?" She suggests hopefully, nudging Dean playfully. He gives her a half smile and nudges her back.

"Yeah, maybe."

"How much longer do you have?"

"A couple of minutes. Tell me about Luke's nephew?"

Something catches Rory's eye and she watches as somebody walks into a bookstore. Something about the way he's dressed has her staring. He looked so familiar…

"Rory?" Dean checks, tucking her hair behind her ear when she doesn't answer. Rory snaps her attention back to him with an apologetic smile.

"Sorry, I just thought…" she trails off before shaking her head. "Never mind. What did you say?"

Dean chuckles.

"Tell me about Luke's nephew," he repeats.

"Oh," Rory says with a shrug. "I haven't met him yet."


"You don't look ready," Luke comments, gesturing outwards with his hands.

"Ready for what?" Jess asks without removing his eyes from his book.

"For dinner. With Lorelai? I told you that was for seven," Luke reminds him, looking at his watch.

"You were serious about that?" Jess groans, putting his book down. "It's only my first night here and you're parading me around like a pony."

Jess and Luke sigh together as Luke comes over to sit on the couch next to Jess's blow up mattress.

"I'm not trying to parade you," Luke apologizes, shrugging his shoulders. "I just thought it'd be good to keep your mind off…"

"Trust me, my mind is on anything but Liz," Jess scoffs with an eye roll, crossing his arms over his chest.

He watches as Luke lifts his hat and smooths back his hair. It's not that he wanted to cause Luke any stress or problems, because really, Luke didn't have to take him in. But it felt easier to blame Luke for agreeing to do it. Why didn't he stick up for him to Liz?

Jess leans his head back against Luke's mattress and closes his eyes. He isn't being fair and he knows it. It wasn't Luke's fault that Liz couldn't handle herself, let alone her kid. A thought of Rory flashes through Jess's mind and his stomach jerks. It wasn't Luke's fault he couldn't stop thinking about the fact he hadn't seen this girl in almost two weeks aside from the small run-in Tuesday, either.

"Okay," Jess finally says, letting out a breath he didn't know he was holding.

"Okay?" Luke asks, confusion on his face.

Jess nods.

"Okay," Luke says, nodding in agreement. He looks at his watch and grimaces. "Can you get dressed in ten minutes?"

Jess nods again and gets up, grabbing a towel and heading to the bathroom. He closes the door behind him.


Luke watches as his nephew skulks off into the bathroom. He runs his hand over his face and takes a deep breath in. He knew this had to be hard for Jess, but he didn't know what else to do besides try.

Luke purses his lips. He wouldn't let his nephew fall through the cracks. He wasn't going to be like his sister. This was something Jess could count on, and Luke really hoped that he knew it.


"You could have worn something other than a hoodie," Luke mumbles, ringing Lorelai's doorbell.

Jess gives him the side eye and stares straight ahead.

"You're right. Like my pajamas. At home," Jess says pointedly, shoving his hands into his pockets.

Luke rolls his eyes.

"I'm just saying," Luke says casually, holding up his hands in mock surrender.

"Yeah, because plaid is so in right now," Jess mocks, gesturing to Luke's outfit.

"What's wrong with my outfit?" Luke protests, gripping at his shirt to look it over.

Jess smirks but doesn't say anything as a woman with blue eyes and auburn hairs opens the door.

"Hi! Come on in guys, the food's almost ready," she says with an excited smile.

Something about her reminds Jess of a windup doll and he isn't sure if that's charming or really annoying. And something about her reminds him of somebody, but he can't put his finger on it. He nods at her and looks at Luke questioningly.

"Thanks. Hey, Lorelai, this is Jess," Luke offers, gesturing at Jess as they step inside.

"I figured. It's so nice to meet you, Jess," Lorelai says, waving her hands around. "I hope you came here with an open slate about me. Luke likes to lie about how wonderful I am."

Jess doesn't really know how to respond to her, so he doesn't. He just offers a pathetic smile and nods, looking around the room.

"Okay, well, great talk," she concedes, clapping her hands together.

Jess walks around the living room, looking at all of the knickknacks. He pretends he doesn't notice Luke and Lorelai having a private conversation about him in the foyer. One photo grabs his attention. It kinda looks like…

"Jess?" Jess turns, hearing Lorelai say his name.

"Why don't you head towards the kitchen and hit the room on the right?" She suggest, waving a hand towards the doorway. "My daughter is in there. From what Luke's told me about you, you guys might hit it off. Just don't hit it off too well, she's got a boyfriend. Not that I'm saying you're the type to hit on a taken girl, you seem very nice. It's just. You know what, you can do what you want, and I'm going to go put my foot in my mouth."

Jess blinks as the rambling woman exchanges an embarrassed look with his uncle. Luke shrugs at Jess before following Lorelai into the kitchen.

He watches as Lorelai leans into the bedroom. He can't catch what her daughter's name is, but he does hear something about 'Luke's nephew is here,' so he figures he should make his grand entrance.

Luke and Lorelai emerge immediately, returning with two strangers. They're all carrying platters and a table, and Jess realizes quickly that he needs to move.

He listens to some crazy argument over a lemon and runs his hand through his hair. There was too much personality happening in this place.

He stares at the entrance to the kitchen and sighs to himself. What did he have to lose, right? The worse thing would be that this girl was hyper like Lorelai. He could probably deal with that for a night.

He shoves his hands into his hoodie pocket and walks lazily through the corridor before sticking his head in the doorway.

"Hey," he says uncertainly.


Rory is so caught up in her homework— that she finally started to do—that she barely registers that somebody's at her door.

"Hey, Rory? Luke's nephew is here," Lorelai informs her, nodding towards the living room. "I told him to come say hi."

"Okay mom," Rory says distractedly, scribbling something in her notebook. She hadn't wanted to work on the logs about Jess, but she thought it might help her get rid of the circular thoughts that were buzzing in her head.

"Okay hon, well, we're gonna get set up, come out in five," Lorelai responds quickly before leaving the doorway.

Rory stares at her paper and smiles. She did feel better about the Jess thing, and seeing Dean had actually really helped her.

"Hey," a voice calls uncertainly.

Rory's eyes widen and her stomach clenches with a vengeance. That voice.

She whips her head around and can't help but gawk.

"Jess?" Rory asks incredulously.

She's thankful that she isn't alone in her shock. Jess stands at the doorway looking as uncomfortable as she feels, a look of disbelief on his face and eyebrows raised in surprise.

"Rory? What the hell?" Jess breathes, his mouth twitching as if he isn't sure whether to smile or not.


No sooner do the words come out of his mouth does Jess feel like he's entering the Twilight zone. Before he's even finished his sentence, Rory springs from her seat at her desk.

That same atmosphere shift from the first two times they were close happens again. The room feels so much smaller than it is. The only thing that Jess can feel is her forehead in the curve of his neck, and the only thing that he can smell is the vanilla scent of her hair.

It feels like they're hugging forever before Jess's senses pick up something other than Rory against him. He realizes somebody is watching them but he doesn't risk turning around. He simply softly nudges Rory, and she pulls apart from him.

He turns around to see nobody there, but he hears Lorelai calling for her daughter.

Jess turns back to face Rory to find her looking panicked.

"I'm, I'm sorry," she mumbles, her face turning red from embarrassment. "I don't know what came over me."

"It's… okay," Jess manages to say, rubbing the back of his head. What did this mean? What the hell was this hug?

"No, it's not, it's breaking some kind of ethics and -"

Jess grabs Rory's hand to stop her from rambling. Having met her mother, he wasn't sure he wanted to see what a less seasoned Gilmore rant might spiral into.

"It's nice to see you too," he says, shifting uncomfortably. This so wasn't his element.

Seeing her face calm and perk up tells him that he said the right thing.

"Really?" She says in a small voice, turning to face him. He nods towards her before nodding towards the door.

"We should go," he says softly. He realizes he's still holding her hand and looks down at it. Rory notices too and pulls her hand back quickly, almost as if burned.

She nods at his suggestion, pausing as if she wants to say something. It seems as though she changes her mind, because she heads outside of the room.

Does this mean she missed me? He thinks to himself. His head is spinning a little and he pinches the bridge of his nose. What was it that Lorelai had said?

'Don't hit it off too well, she's got a boyfriend.'

Jess groans. A boyfriend. So what the hell was all of this?

He really needed an aspirin. Or a beer.

The latter sounds like the better option and he skips following Rory into the living room, instead opening up the refrigerator to find what he was looking for.

He grabs a beer from the fridge and glances towards the other room, where the voices are beginning to carry. He shakes his head. Nope, not going out there.

He grips the bottle and heads out the back door for some fresh air.


AN: Thanks for reading :) Reviews are always welcome and appreciated xo