Chapter 1 Notes: Trying out a new story idea. Please let me know if there is any interest in continuing with this concept. Sorry, the notes are so vague, but I don't want to give away too much of the story before you read the first chapter! Thanks for reading, and all reviews and thoughts are warmly welcomed.

Disclaimer: I own nothing except my own obsession with Gilmore Girls.

Trigger Warning: This story will feature homelessness. Also, this chapter contains two deaths of minor characters. The deaths occur 'off-camera,' but will be mourned by a main character throughout the story.

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Jess let himself into his tiny studio apartment and dropped his bag. He took off his hat, his jacket and his gloves leaving them in a pile by the door, his mind still processing what he had just seen. He had been walking home from his job at Kinko's, head down against the bitter cold, when he had glanced up and spotted a familiar figure turning from a side street and joining the flow of pedestrian traffic on the sidewalk a few feet in front of him. He had been instantly transported back to Stars Hollow, his heart pounding with the beginning of a fight or flight response. He had kept a reasonable distance between them as he followed, his eyes glued to their mark. About two blocks from his apartment, Jess had watched the figure stop and join the long line of men that formed outside St. Sebastian's every night. Jess had stopped short in surprise and had promptly been bumped by someone from behind. He had barely registered the, "Watch what you're doing, asshole!" hurled his way, the New York City version of excuse me. The moment had felt surreal. Jess had needed to confirm what he had seen. He had resumed walking, but at a slower pace, and sent a furtive glance toward the line of men as he lowered his head and made his way past. He had been right. It was definitely him. But, it made no sense. What the hell was Dean Forrester doing waiting in line at a homeless shelter in New York City of all places?

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Jess couldn't stop thinking about Dean as he heated up chili on the stove top for dinner. He decided he would call Luke after he ate to see if he knew anything about what was going on with Dean. But, first things first. He was starving. He removed the pot from the flame and poured the contents into a bowl. He stood at the counter, spooning the steaming chili into his mouth and thinking. After he was done with dinner and had washed his bowl and pot, he retrieved his cell phone from his jacket pocket and dialed the person he called the most. His uncle picked up on the second ring.

"Hey, Jess! I'm glad you called."

"Hey, Luke. Is now an ok time? Do you have a few minutes?"

"For you? Always. Just give me one minute. I'm going to step into the storage room so I can hear you better." Jess heard Luke call to Caesar that he'll be back in a few minutes, and it dawned on him that the dinner rush would still be going on at the diner. He probably should have waited another hour before he called. "Ok, I'm good now."

Jess smirked. "I thought there was a strict no cell phone policy in the diner. I'd hate to see you get in trouble at work. From what I remember, the boss is a real hardass."

Luke laughed. "He still is, but he's got a soft spot for when his favorite nephew calls."

"Aww, it's nice to know I get special treatment."

"How are you, Jess? Is everything ok?" They normally spoke every week, but almost always on Sunday nights. The few calls Luke had received from Jess on weeknights since the boy had moved to New York were usually indicative that something was wrong or that Jess was especially lonely and feeling down.

"Yeah. Yeah, Luke. I'm good." Now that Jess had his uncle on the phone, he wasn't sure how to ask what he wanted to know without it sounding weird.

"Good, I'm glad to hear it. So, what's up? Just missed me?"

"Actually, I was, uh, just calling to ask you something. It might sound strange, but what do you know about what Dean is up to these days?"

"Dean? Dean Forrester?" Jess could hear the surprise in Luke's voice.

"That's the one."

"Dean, your old high school nemesis? That Dean?"

"The very same."

"Why are you asking about Dean?" Luke's voice became more serious. "Did you hear about his family?"

"What do you mean? I haven't heard anything. That's why I'm asking."

"But, what brought this up? Why are you asking me about Dean now?"

"I think I might have seen him today. In New York. But, I'm not sure. I was just wondering if it really could have been him, or if he's still accounted for as a resident of Stars Hollow."

Luke paused. "It probably was Dean that you saw. He moved to New York. About a week after he graduated high school, his parents were in a car accident in Hartford. They got hit by a drunk driver, and neither of them made it. Dean and his little sister went to live with their aunt and uncle in New York. Dean had gotten into a college in Connecticut, but he was going to try to transfer to somewhere in New York so that he could be with his sister. It's very sad. I didn't know his parents very well, but they seemed like nice people. And, with his little sister being so young still… It was a real tragedy."

"Huh. That sucks."

"Yes, it certainly does suck, nephew."

"How come you never told me about it?"

"I don't know. You were in California when it happened. We weren't really talking at the time. By the time you came back and we reconnected, I guess it just didn't come up."

"Huh."

"If you run into him again, be nice. I'm sure he could use a friend right about now."

"We were never friends, Luke." Jess was surprised to hear the defensiveness in his own voice.

"I know that. I'm just saying, if you see him again, keep in mind what he's going through and be nice anyway. He might not have a lot of friends in New York yet, and he might appreciate seeing a familiar face. Maybe, without Rory to fight over, you guys can get past your high school crap and get along. That's all I'm saying."

Jess sighed. He wasn't sure why he wasn't telling Luke about the shelter. It somehow seemed too personal to talk about without knowing whether Dean was ok with people knowing about his situation.

"How are you doing otherwise, Jess? You staying warm?"

"Yeah. I'm trying. It's been brutal lately."

"Well, it's only going to get worse. I saw on the news this morning that New York is expecting temperatures in the single digits for the next week and a half. It's supposed to set a record for coldest January on the books. We're supposed to fare a little better over here with some days getting into the mid to high teens."

"Jeez, another week and a half of this shit? I should have stayed in freakin' California." Jess went through the motions of complaining about the weather, but his mind had already gone back to Dean, wondering what he did all day and how he kept himself warm when he wasn't in the shelter.

Luke chuckled. "Well, I for one am glad you didn't. You good, though? You still got all those blankets and quilts and everything? Your heat is working? You need anything?"

"I'm good, Luke. Yeah, I still have the blankets you gave me. The heat is working fine."

"And, you're using it right? You have the heat on enough to be comfortable?" Luke knew that Jess struggled with money and didn't turn the heat as high as Luke would like him to because of the cost. Luke worried about that, and about Jess' living situation in general.

"Yeah, I have the heat on. I'm fine."

"I don't know if you've been following the news, but there's a particularly nasty flu epidemic going around this year."

"The flu is a virus, Luke. You don't get it from being cold. Or having wet hair. Those are old wives' tales."

"I know that, smart guy. But, being cold lowers your body's natural resistance and makes you more susceptible to picking up the virus and getting sick. And, several otherwise healthy adults have died from the flu already this winter. It's really serious this year, and I just want to make sure you're taking care of yourself." Luke paused. "You're not here for me to check up on anymore, so I need you to tell me that you're taking care of yourself."

Jess softened at his uncle's concern. "I'm taking care of myself, Luke. I promise. I have the heat set to a reasonable temperature, I'm eating lots of soup and chili, and I go to sleep at night in the flannel pajamas you gave me for Christmas while wrapped in a comfy and cozy nest of the quilts that your mom made. You don't need to worry about me. I'm good."

Jess could hear the smile in his uncle's response. "Glad to hear it. And if you need anything, help with a heating bill, or anything, you'll let me know, right?"

"Yes, Luke. I will. But, right now, I really am ok."

"All right. I want to go out there soon to check out your new apartment and take you to lunch. When is good for you?"

"I'm not sure. I'll check my work schedule tomorrow and text you."

"Ok, Jess, sounds good."

"I'll let you get back to work now."

"All right, Jess. It was good talking to you. It's always good to hear your voice."

"Same here. 'Bye, Luke."

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After getting off the phone with Luke, Jess tried to settle down and read a book, but he couldn't focus. His mind kept wandering back to Dean. Jess wondered if he had misread what he had seen entirely. He really didn't know what Dean's situation was. Maybe he was making too many assumptions. It was possible the guy really was living with his aunt and uncle and was only volunteering at the shelter because he was the kind of kiss-ass do-gooder who did stuff like that. Maybe even for school credit or something. That thought brought Jess a measure of relief. But, his mind still wouldn't let him rest. Wouldn't the shelter have a separate entrance for volunteers? Or, wouldn't the volunteers be allowed in early to prepare the food instead of lining up outside in the cold with the shelter clientele? And, he hadn't liked the way Dean looked. His general level of dishevelment. Hair longer than he had seen him wear it before. Scruffy facial hair. Dirty, stuffed backpack on his shoulder. Head down against the cold and the wind as he walked. Eyes downcast in front of him as he stood in line waiting for shelter. He had had a hopeless look that had felt familiar to Jess. It called to mind his own brief period of homelessness, when he had run off to California after Luke had told him he needed to leave if he wouldn't go back to school only to find that he hadn't really been welcome in California either. He hated thinking about that period of his life, and he knew he would end up depressed if he let his mind linger on that time for too long. Jess sighed and put down his book. He put on his headphones, blasted whatever was in his CD player and tried to empty his mind and go to sleep. On nights like these, he really wished he could afford a television for distraction.

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After checking his work schedule at Kinko's, Jess had made a plan to get together with Luke. His uncle was going to come out to New York a week from Sunday. Jess was looking forward to seeing Luke, but once the date was set, he found himself surveying his tiny apartment, trying to see it through Luke's eyes. He took in the twin mattress on the floor. The two plastic storage containers with pull out drawers, one full of clothes and one of books and CD's. The foot and a half of counter space above the mini-fridge in the kitchen area. The stovetop with two small electric burners, but no oven. The narrowest shower he had ever been in. And the one very dirty window. He sighed. At least he could clean the window. Jess knew that this apartment was a great find, but he didn't think Luke would see it that way, and he didn't want his uncle to worry about him, or worse, pity him. He wanted Luke to see him as an adult, capable of living on his own and taking care of himself. Jess lived in a very small, studio apartment that was owned by a co-worker's family. It was originally a room in the family's apartment that they had walled off to create a rental space for extra income. They had added a tiny bathroom and an exit to the hallway, but in the end, it hadn't passed the size requirements stipulated in the zoning laws to qualify as a rental unit. It might be smaller than a standard studio apartment, but the upshot of this construction blunder for Jess was that the family was only able to rent it out on a cash basis to people they knew and trusted not to report them, greatly reducing the competition for the apartment as well as the price. The downside was that Jess had no official lease for the apartment. Luke had been skeptical when Jess explained the situation, worried about what Jess was getting himself into by renting from a landlord who couldn't even manage to set up a rental until correctly. Luke had relaxed a little when Jess had assured him that the room had its own entrance to the hallway as well as a second means of egress in the form of a fire escape off the apartment's only window. When he had first moved back to New York, Jess had originally moved into a much larger one room apartment with a friend and two other guys. He had always been aware that he required a lot of alone time, but he hadn't expected living with roommates to be so trying for him. He had chocked it up as a necessary evil to be able to afford to live in the city, and in the warmer months, when he could spend hours outside on his days off reading or people watching, it hadn't been so bad. When summer turned into autumn and then winter, Jess had started spending his free time at the library to avoid being in his cramped apartment, where it often felt too loud to think, never mind read or write. When his co-worker had told him about his parents' mini-studio and that their current tenant was moving out, Jess had jumped on the opportunity. He was paying more now than he had at his last place, but by a small enough margin to make it feel worthwhile. He loved having his own space. When he had to scrimp on costs in other areas, like food and heat, he reminded himself that coming home to solitude every night was priceless.

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Jess learned that St. Sebastian's shelter opened its doors at seven o'clock every night. He normally finished his shift at Kinkos at six o'clock and had a twenty-minute walk back to his neighborhood. In the evenings after seeing Dean, Jess found himself incorporating something new into his routine as he began to slow his pace in front of the shelter and take notice of the line of men that he had barely given a passing thought to prior to this week. Most evenings, he examined the line with discreet, sidelong glances, not wanting to stare or catch anyone's eye as he moved through the cold. The men seemed to cluster together in a bunched-up line against the side of the building, probably for warmth, often making it difficult to distinguish individual forms in the dark. One evening a few days after his first sighting, Jess spotted Dean in line. Even with his shoulders slouched and his head down, Dean still stood out as he loomed a half a head above the men standing closest to him. Jess stopped in his tracks, feeling panicked and conflicted. He and Dean weren't friends, not by a long shot. He can still remember Dean sucker punching him at Kyle's party and the fight that ensued. He can still remember the intense feelings of hatred he harbored every time he saw the other boy with Rory or had to witness the smug smile on his face when he felt that he had one-upped Jess in some way, but he no longer actually felt the anger and hatred, he just held the memory of it. He felt like he should do something, but he wasn't sure what. Did he really have some kind of responsibility toward Dean just because they had both lived in the same town, however briefly? Dated the same girl, gone to the same school, aggravated the shit out of each other? It wasn't a solid connection. He had no positive connotations associated with Dean. But, he couldn't deny that he knew him. Had sat behind him in English class. Bought batteries from him at the market. Met his little sister at the winter carnival. It was a connection, in a city full of transient passersby and anonymous interactions. Would Dean even want to see him? Or accept his help? What did Jess even have to offer him, anyway? He was probably the last person Dean would want seeing him like this. Jess pulled his hat down lower over his ears and continued his walk home. Laying in his bed that night, he couldn't sleep. He kept thinking about Dean and how desperate he must feel to be seeking refuge in a shelter. Maybe Jess was wrong about how Dean would react to him. He wondered what happened with the aunt and uncle and where Clara was. He snuggled into his warm bed, grateful to have this tiny room to go to every night and a warm, relatively safe place to sleep. He wondered what it was like in the shelter. What the conditions were like. And the other people. Whether Dean felt safe or scared. If he could sleep.

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One day the following week, Jess got stuck at work an extra hour because a co-worker had gone home sick. The weather still felt punishing and Jess was miserable on his walk home, cold, tired and hungry. He looked toward the shelter out of habit. No line. It was around twenty past seven so he assumed everyone must already be inside. He walked on, trying not to think about it. A half a block later, he spotted a recognizable figure moving in the dark, a few feet inside an alley, digging through a dumpster, pulling out what looked like a large piece of cardboard. Jess stood as if frozen in place, watching Dean dig through the trash, wondering why he wasn't in the shelter. Jess watched as Dean added the cardboard to a stack on the ground and then squatted down in front of it. He propped a couple of layers of cardboard against the wall and slid the rest near the wall on the ground, making a little cardboard chair. He lowered a gloved hand to the cardboard on the ground as if testing it for something, then he turned and sat in his makeshift cardboard chair. He pulled his backpack against his side and weaving one arm through the shoulder strap, wrapped his arms around the tops of his raised knees and lowered his head. The night was unusually quiet for this neighborhood, but Jess still couldn't be sure if it was his imagination or if he had really made out a small sniffle and a quiet sob. He watched as Dean's shoulders started to shake, knowing he wasn't imagining that, and he snapped out of his shock. He knew he needed to do something now. He could no longer convince himself that this wasn't his business. Dean could die out here tonight. Certainly, it was worth some potentially awkward conversation to keep that from happening. He thought about what Luke would do in this situation. And what Luke would want him to do. He took a deep breath and headed into the alley.

Author Notes:

Right now, I am thinking this story will take place mainly in NYC and mostly focus on Jess and Dean. I already have a couple of ideas that will bring Luke to the city to check on the boys, but he won't be as front and center of a character as he usually is in my stories. Please let me know if there is interest in this story idea. All feedback is welcome and appreciated. Thank you.