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Chapter 1

Thanksgiving, 2007

The car shuddered as he pulled to a stop at a gas station somewhere on I-95 in Connecticut. He had crossed the state line from New York a while ago, but the old car wasn't going to make it all the way to Stars Hollow without a fill up. It was a perpetually needy heap of rusted metal on sagging wheels. He was a self-admitted idiot for continuing to try to get it to run.

He slammed the car door shut and fiddled with the pump. When the hose was propped up, and gas slowly began trickling into the tank, he leaned against the car door and pulled out his battered phone.

Luke had texted him. Where are you?

He responded quickly. In CT. Should be there soon.

Jess had been roped into Thanksgiving with Luke and Lorelai when Liz announced that she and TJ were heading to a medieval feast somewhere in nowhere Pennsylvania. Jess didn't care much about Thanksgiving; he normally spent the holiday with a bottle of whiskey and a book, but Luke had a different vision this year. He wanted a proper Thanksgiving with Lorelai and her family, and had even offered to host at the diner. Jess was informed by a gruff phone call that it would mean a lot to Luke if he attended. So, though his friends at the printing press tried to coax him into staying for a proper bachelors' dinner of take out and six packs, he ended up packing late Thursday morning, firing up the old car, and heading towards his old, bumbling little town.

He sighed, and checked the pump. The bottle of whiskey would still be there when he got back. Hopefully the guys wouldn't burn the shop down in the meantime.

He returned the pump, crumpled his receipt, and tossed it in the trash. He was already running late.

When Jess pulled up in front of the diner he was faintly surprised to see how many people were milling about inside. He exhaled, leaning back in his seat. He didn't particularly want to go in and get the usual scowls from the goodhearted townspeople that would never forgive him for his seventeen-year-old self's leather jacket and cigarettes. But he had made a promise to Luke, and perhaps it was time that he began to reacquaint himself with the eccentric crowd that was Stars Hollow. He was older, more mature, and didn't really give a damn what anyone thought of him. And if Luke's unbearable happiness over the phone was any indication, he and Lorelai were going to be together for a very, very long time. Jess may as well get used to visiting more.

He locked his car and slipped the keys into the pocket of his dark jeans. Then he hurried up the steps, opened the door, and slipped quietly into the chaos.

Jess was struck immediately by a familiar mix of smells: coffee grinds, burgers, Clorox, and by the chattering din that filled the small space. He winced at the sensory overload.

It appeared as though Luke and Lorelai had decided to host a combined Thanksgiving for their families, and then half the town showed up as well. Jess recognized Lorelai's parents, holding court over by the cocktail cart, and April tucked up on a stool reading a book. There was a long, decorated table with 14 or so places set by the window, but various townspeople crowded every other seat, happily chatting and gossiping and nursing coffees. Jess stood on his toes, straining to see Luke in the crowd.

He spotted his uncle by the phone, looking entirely panicked. Jess ducked between tables and sidled up to the counter.

"Jess!" Luke gave him a quick, one-armed hug, then gestured at the tables, slightly manic, "Look at this! Can you believe it? Kirk overheard Lorelai on the phone and put up flyers announcing 'Family Thanksgiving' at Luke's to the town. I'm going to kill him!"

Jess raised his eyebrows. "You can't kick them out?"

"Believe me, I've tried," Luke scowled and gripped the counter. "I can't get anyone to leave. They said they didn't make plans because they were going to come here. I don't have enough food! And I'm not going to feed them our Thanksgiving dinner. Parasites."

Jess saw Kirk sitting at one of the tables, knife and fork in hands, staring expectantly at Luke. Jess couldn't help but crack a half-smile. "Can you get Lorelai to do it?"

"She's trying," Luke pointed. Jess saw Lorelai pleading with Babette, gesturing at the kitchen hopelessly. Luke groaned, "I don't know how we're going to get out of this. Our food is ready but we can't eat it with all of them in here!"

Jess glanced at him. "Well, you do have plenty of food here."

"Sure, but not Thanksgiving food. Not our food. Kirk requested gluten-free stuffing, can you believe him? I said no and he handed me a recipe! Ten minutes ago! The nerve."

Jess clapped him on the shoulder, "Well, beggars can't be choosers. Tell them they can have cheeseburgers or they can leave. Cheeseburgers to go."

Luke thought about it. Before he could respond, Lorelai popped up in front of the counter. "No luck hon, they're sticking to us like glue. I tried to explain that we're not a soup kitchen, that this is for family, and Babette gave me those big eyes and said, 'Of course sweetie, we are your family!' Luke, if I don't get to eat at least nine helpings of Thanksgiving food, there's no telling what I may do. I'm desperate. There will be consequences. Dire consequences."

She paused, and turned to Jess. "Hi, troublemaker. Glad you could make it." Then she turned back to Luke, but before she could continue ranting, he cut her off.

"Jess says we could give them cheeseburgers to go. What do you think?"

Lorelai went from fake-tearful to grinning in half a second. "Brilliant. Love it. Send them on their way with greasy food. Can you cook that many that fast?"

Luke was already firing up the grill. "Sure. Jess can help me."

Jess rolled his eyes, but went ahead and slipped off his dark gray blazer and hung it on a hook. He headed back towards the freezer. Five minutes in Stars Hollow and he was back to being a waiter and pissing off townspeople. This town was an incorrigible broken time machine.

It didn't take long for him to pick up his minimum wage labor habits again. Within half an hour he and Luke had boxed up twenty or so cheeseburgers and stuffed them in boxes with triple servings of fries. Lorelai scooped them up and handed them out as people left. "Thanks for coming you all, sorry our oven broke!" She patted Kirk on the shoulder, "Here you go, Kirk, lettuce bun for you."

The chattering crowd filed out more or less amicably, dispersing into the town square for a picnic style Thanksgiving. When the place was empty (Luke and Lorelai had to escort Taylor out policemen-style) Luke slammed and locked the door.

"Well heavens," Lorelai's mother had a hand on her hip, "do you always have that many vagrants in here? Where do they all come from? Shouldn't you call the police?"

"Mom, I would, but the cop was here too. Gin martini please?" Lorelai looked pointedly at the cocktail cart. Her mother shot her a withering look, but primly turned around and began fixing a drink for her daughter.

Jess took in the remaining group as he washed and dried his hands. He knew almost all of them: Lorelai's parents, April, Sookie, Jackson, and a couple kids that he assumed belonged to them.

There was no sign of Rory, but he wasn't sure he minded. The last time he had seen her had been the painful evening in Truncheon, when she had come to him confused and scattered and desperate. He had sewed up that part of his heart neatly in prose and cauterized it with alcohol, long before her visit to his print shop, but it still ached occasionally when provoked. Her kiss in Philadelphia and subsequent spill of panic and emotion – admitting to being in love with her douchebag boyfriend - had hit him like an unexpected punch to the gut. It was probably easier not to see her.

"Anyone else?" Emily handed Lorelai a martini. She raised her eyebrows at Jess. "You?"

"Whiskey, neat," he requested. He shrugged on his blazer. He needed a drink.

Lorelai's father toasted him, "That a boy."

Jess leaned against the counter by April, swirling his whiskey, as the group hurried to draw curtains and pull the contraband Thanksgiving food from the not-broken oven and the other cabinets and cupboards that Lorelai had thrown things into. "Don't worry kids, we're only twenty minutes or so away from eating," Lorelai assured them as she pulled a ziplock bag of dinner rolls from where they had been taped underneath the stool next to April.

April shook her head, not looking up from her book, "This is ridiculous."

Jess sipped his whiskey. "This is Stars Hollow."

The flurry of activity continued until Jess and April were eventually shooed into seats at the table by Sookie. Jess felt most comfortable next to April, who continued to read her book under the table and did not bother to engage him in conversation. He watched the madness, vaguely amused, observing the endless banter.

Finally, everyone drew up chairs. Lorelai lit the candles. She sat next to Luke, but there was an empty chair to her right.

Luke cleared his throat. "I, uh, I want to thank all of you for being here with us today. It means a lot to me and Lorelai to have all of you here together, for this meal, without Kirk."

"We love all of you," Lorelai beamed.

Luke raised a glass, "A toast, to family and friends, and -"

There was a quiet knock on the door that cut him off mid-sentence. Luke jumped up from the table, "I swear to god, Kirk, if that's you, I'm going to kill you."

They all watched as he peeked through the curtain, and then visibly relaxed. "Rory!" he quickly opened the door, "we didn't think you were going to make it until later!"

"Hi Luke," she stepped in, giving him a hug, "Yeah, I managed to sneak off the trail early and grab a morning train. Did I make it in time?"

"You sure did," he grinned and re-locked the door, ushering her towards the table.

"Hi kiddo!" Lorelai leaped up and gave her daughter a hug.

"Hi everyone," Rory waved at the table, "hi Grandma, hi Grandpa." She settled in her chair, smiling at the group, and caught eyes with Jess.

Jess was unsurprised at how calm he felt. They had left things awkwardly last time, but it was not through any fault of his own. A three-day binge on alcohol with his roommates had been enough to forget that night, forget his ex-girlfriend, and re-seal that piece in him that had been battered by her visit.

He tipped his glass to her, and offered a half-smile. She returned it, but he could see her happiness fall ever so slightly, a crease of guilt appearing between her brows.

Luke resumed his toast, buoyed by Rory's arrival. Jess watched his uncle, appreciating his sentimental toast, and then raised his glass to join in and cheer the holiday.

The dinner flew by in a hazy blur of merry conversation, unexpectedly good food (Jess forgot how talented his uncle and Sookie were at these things), and a few more glasses of whiskey. Lorelai's father, Richard, took it upon himself to continuously refill both of their glasses and engage him in a long and detailed discussion of book publishing and the effects of future online sales. Jess rather enjoyed speaking with him. By the time the pecan and pumpkin pies were being passed around, Richard had pulled Emily aside no less than three times to say, "Emily, did you here what this young man just said? Remarkable, this business!"

Jess caught Rory's eyes on him only once, after her grandfather's second exclamation, but did not linger to maintain eye contact. He was beginning to feel the heady influence of alcohol, and could feel the tenseness in his shoulders unknotting. He was starting to suspect that he liked this odd, close-knit crowd of Luke and Lorelai's.

By the time dinner ended the sun had long gone down, and the chill of the dark, late autumn night caused Luke to pull out a space heater. Lorelai had her feet in his lap, her fourth slice of pie balanced on her armrest. The group rearranged more or less into a circle of chairs. Jess made a pot of coffee (to try to balance out the excess whiskey in his bloodstream) and drank a mug of it on a high stool by the counter, watching the group, catching snatches of various conversations.

Rory was perched on a chair leaning close to her mother, the two of them cheerfully gossiping. Sookie and Jackson seemed intent on trying to dissuade their children from using their crayons on the floor. Luke chatted with Lorelai's parents, more at ease than Jess had ever seen him with them. Despite himself, he enjoyed the warmth of the moment.

Soon enough Sookie and Jackson took their children home and to bed, and Emily and Richard bustled out the door after a series of goodbyes. Richard shook Jess' hand firmly, "I hope to see you again young man, I have some more questions. And it's always good to know a good publisher."

Jess returned the shake, "Thanks for the evening and the whiskey."

Richard winked and let Emily pull him out the door.

Jess and Luke started doing the dishes together, cleaning up and letting the three women – Lorelai, Rory, and April – drink coffee and catch up. Jess swore he could still see a corner of April's book under the table.

When most everything was cleaned up, and Luke was resting against the counter, waiting for the dish washer to cycle through, Jess clapped him on the shoulder and told him he would be outside for a minute. He slipped out the door and into the cold, dark autumn night.

This town would never change. He leaned against the wall of the diner, looking out at the gazebo and the square, all done up with festive holiday decorations. In his pocket he toyed with his lighter and thought of the pack of cigarettes tucked somewhere in his glove compartment.

Jess heard the door creak open again. He glanced up and saw her familiar figure. "Hey."

Rory stepped down. "Hey. Was hoping to catch you for a minute."

"Consider me caught," he looked back towards the town square, "what's new, Gilmore?"

She shrugged and leaned against the wall also, making sure to leave at least two feet of space between them. She wasn't wearing her coat, and crossed her arms tightly to preserve warmth in her sweater. "Crazy day, huh? Mom told me about Kirk and Babette and everyone. Thanks for helping to save their Thanksgiving."

He didn't try to suppress his sarcasm. "I was thankful for the opportunity to kick all of them out."

Rory smiled, "I figured."

They lapsed into quiet for another minute. Jess was now toying with both his lighter and his car keys in his pocket, urging for a smoke but trying his best not to, because he knew he was an idiot for keeping cigarettes in his car anyway when he was trying to quit.

"So, what's new with you?" He turned towards her, leaning his shoulder into the wall, focusing intently to try to wrench his thoughts away from his glove box. "You graduate yet? Where are you these days?"

"Yep, graduated," she raised herself a few centimeters taller, "I'm kind of all over right now, working on Senator Obama's campaign. Different city every few days. You know, living that vagabond On the Road existence we always dreamed of, except this one has a lot more red white and blue streamers and targeted bumper sticker slogans."

Jess snorted. "A regular Kerouac you are. Do you hitchhike on the campaign busses?"

"Oh yeah, sleep under the stars in Iowa, urge my boss to continue to go west, the whole bit."

Jess couldn't help but grin. He was helpless to a woman who could quote Kerouac.

"What about you?" she looked up at him, blue eyes calmer, more relaxed from their banter, "how's Truncheon? Write another book yet?"

"There may be one in the making," Jess replied casually, "but to be honest, I only think it isn't garbage when it's four in the morning and I'm high on alcohol and sleep deprivation. I can't see it living beyond the pages of a notebook where hopefully no one will ever have the misfortune of reading it, let alone paying for it."

"No way," Rory exclaimed, "come on, Jess, let it live. Every artist is his own worst critic. I'm sure it's amazing, just like Subsect."

"It is what it is," Jess shrugged.

"You know, I have worked as an editor," Rory tilted her head, smiling, "you could send it to me. I would be happy to let you know how truly, ridiculously talented you are."

Her flattery was sweet, but he shook his head. "You'd have to give me the most brutal, cutthroat, Yale-editor feedback in your repertoire. None of that confidence boosting or hand holding. If you didn't send it back shredded, I'd be frankly disappointed."

"Alright," she agreed, her smile growing, "so much red pen you couldn't read the original words. A scathing editorial review. A dream-crushing blitzkrieg of brutal, honest criticism."

"That's better," Jess nodded. "Alright Gilmore, keep a look out on the road. You may stumble across a manila envelope in Iowa somewhere that's full of alcoholic rambling begging for a proper beat down."

"Deal," she offered her hand.

He hesitated for a millisecond, and then pulled his hand from his pocket and shook her hand. Her skin was icy cold.

"You should get inside," he shoved his hands back in his pockets, "you may freeze to death and then I'll have no editor."

"I'm fine," she re-crossed her arms. He watched her bite her lip, hesitating. Then she sighed. "I actually have been meaning to talk to you for a while, to apologize for last time."

Jess stayed quiet, his eyes on her, waiting. Snatches of their last conversation in Truncheon floated through his memory, but he ignored them. Idly, he wondered if she was still with that blonde boyfriend that she had wanted to cheat on but couldn't. He wouldn't be surprised.

"I was an idiot, a total idiot, and I'm so sorry for dragging you into my mess. You really didn't deserve it," she shifted, uncomfortable, "I've been wanting to reach out to you, to get rid of the awkwardness, but I didn't want to do it over the phone or anything."

He watched her carefully. She seemed to stumble, unsure how to phrase what she wanted to say.

"You're just – you're more important to me than how I made it look that night. I shouldn't have used you, or visited you alone, and I want you to know how entirely my fault that entire situation was. And -"

"Rory," he interrupted, "it's really okay."

She bit her lip, staring at him.

"Seriously," he shifted his weight, "I get it. It wasn't the greatest thing you've ever done, but people do crazy things when they're in pain and in love."

Rory appreciated this. She glanced back out at the gazebo. "Yeah, they do."

"So how did that end up?" Jess asked after a pause. He had other biting commentary that he could have added, but restrained. Rory had lived with his running opinions on her boyfriend before; he knew that she could fill in the blanks of his less-than-impressed opinions.

She sighed, "Recently ended. More or less amicably. He wanted more than I was willing to give at this point in my life."

Jess read the subtext. He let it sink in, contemplative.

"Anyway," she stood up straight, pushing herself off of the wall, "I really just wanted to let you know that I'm sorry, and that I appreciate you a lot more than what I showed in Truncheon. Chalk it up to a continuation of Rory: The emotionally stupid college years."

He chuckled. "We all have those years. Some of us are just more emotionally stupid than others."

There was a long pause. He gripped his lighter in his pocket. "Rory, I think that there is a lot that we could apologize to each other for. Let's just agree to be less stupid to each other in the future."

She nodded, her blue eyes fixed on his. "Agreed."

Jess held the eye contact for a long moment, searching her. Then he pushed off the wall, gave a light tug on her sleeve, and moved past her, back towards the door of the diner. "See you inside."

He could feel her eyes on him as he opened the door and re-entered the warmth of the diner, but it didn't bother him. The shredded teenage part of his heart was quiet, still, unaffected. Perhaps this was what adulthood looked like to him now, being able to be calm and sensitive around a person that had once made him feel like he was suffocating and choking on his own desperate, unquenchable emotion. Jess appreciated Rory's apology, but he didn't feel changed because of it. He had closed her door years ago, and locked it with an extra deadbolt after her painful visit to the publishing house.

When she came back inside the diner she gave him a small smile, but kept her space and distance. Jess allowed himself to sink a little deeper into his whiskey. He flipped her words over in his head, musing.

Later that night, as he lay in his old bed in the apartment above the diner, drowsy from Thanksgiving food, whiskey, and nostalgia, he pictured her in her old room at Luke and Lorelai's house. They were both too old for this, too old for these old rooms and twin beds and teenage memories.

Jess remembered her editor blitzkrieg comment, and smiled in spite of himself. Maybe he would send a chapter of his shitty writing to her, for the sake of feedback or artistic growth or masochism. Or maybe he would just run into her again at some family holiday, during all of the future instances that he knew he would be pulled back to Stars Hollow and back to Luke. He could let this be, let himself be an artist without her banter and blue eyes finding their way into the literary strings of his writing.

He rolled over and gently did his best to push Rory out of his thoughts and out of his memories.