A/n: This is a story about swapping Rory and Jess's lives. Jess is now the son of Lorelai Gilmore and Rory is the daughter of Liz Danes. That's all you need to know for now. Please enjoy.

Jess walked down the sidewalk of Main Street as the bitter cold nipped at his face. It was one of those early cold-fronts that happened sometimes in New England's September. Weather here was typically temperamental. The street was lined with many stores, such as restaurants, bookstores and multiple shops that specialized in porcelain unicorns. To Jess's left was the town square. A couple dressed in puffy coats and knitted hats were sitting on the gazebo sipping hot chocolate out of to-go cups from Luke's Diner.

Instead of focusing on his path Jess's gaze was enthralled by his worn down copy of The Old Man and the Sea, one of his old favorites. Its margins were already chock full of Jess's annotations, but he was scribbling away more notes nonetheless.

When he reached the street corner between Doose's Market and the flower shop Jess didn't bother to look both ways for cars. He just stepped off the curb and trusted that the drivers weren't speeding past fifteen miles per hour. He didn't look out for other pedestrians either. Everyone in Stars Hollow knew Jess, and they knew if he was walking their way with a book in his hands then it was their job to jump out of his way.

As Jess crossed the street a car stopped short just a foot or two shy from hitting him. Jess didn't even notice, he just kept walking.

A block later he reached Luke's Diner. A patron exited the diner and held the door for Jess, who still wasn't paying any attention to his surroundings. Jess stood in the doorway for a few moments while he finished his paragraph then looked up to find where the woman he was meeting was sitting. Once he sat down at her table he went back to reading his book. It only took a few seconds, though, for her to snatch it out of his hands.

Jess looked up, his eyes at first were wide with surprise before turning into an angry glare. Sitting across from him his mother, Lorelai Gilmore, was grinning devilishly.

"You'll thank me," she said. "One of these days you'll trip."

"I'm already sitting. How can I trip?"

"It's preemptive."

"Let me finish the chapter," Jess begged. His begging needed work. It came out more like a demand, which he knew never worked on his mother.

Lorelai ignored him and rested the book on her lap. She picked up her coffee cup and took a long sip, complete with slurping sounds. When she put her mug back on the table her eyes caught the empty mug in front of Jess. She picked it up. "Want?"

"Yes ma'am!" Jess said with forced pep.

Lorelai stood and left the book on her chair, just out of Jess's reach. As soon as she was distracted by the diner proprietor, Luke, Jess reached over the table and grabbed his book back. He vaguely overheard bits and pieces of an argument between Lorelai and Luke, it involved Luke accusing Lorelai of being a junkie, before she returned with Jess's cup.

Lorelai gasped dramatically and held a pointed finger at her son while standing over him. "You tricked me!" she said.

Jess smirked without taking his eyes off the book. He'd never admit it to her but his mother's flair for dramatics always amused him. Still, he'd rather be reading then being sucked into her nonsense. He tried to block Lorelai out and focus on Hemingway's concise words.

Lorelai sat back down beside him and put the coffee cup in front of Jess. Jess ignored it.

"Did you even want your coffee?" Lorelai asked.

Jess shrugged. No, he didn't. Coffee was his mother's obsession, not his.

"So it really was just all a trick?"

Jess peered up at his mother. There was a look a betrayal on her face. Jess had to suppress his laughter. He hid his face with the book, but his trembling shoulders gave him away.

"Heresy!" Lorelai said. She knew she had won over his attention and she was going to pump it for all it was worth. "We do not take coffee in vain. It is our life force. Our savior. Our holy ghost."

Jess pushed the coffee toward his mother. "Need another?"

She picked it up and took a large gulp. "Thank you. I was really running low today. I'm better." Her dramatics were over. At least for now.

"How much have you had today?" Jess asked.

"Now don't you go accusing me of being a junkie too!" Lorelai wagged her finger at Jess.

"What?"

Lorelai pouted. The dramatics were back. It was Jess's fault. He knew what happens when he engaged with his mother's outlandish ideas. "Luke called me a junkie when I told him I already had five cups today."

Jess snickered and tried to hide his face with the book again. "You are," he said under his breath.

"Hey!" she clearly heard it. She slapped his arm playfully. "Be nice to me. I am your mother. I gave you life. And since coffee gives me life, by the transitive property it gives you life too. So be nice to coffee!"

Jess closed his book. She won. He wasn't getting any more reading done and as much as he hated to admit it he was actually enjoying the banter a little. "I'm sorry coffee," Jess said, pretending to speak to Lorelai's coffee cups. "I'm sorry I gave you up and let a crazy-lady take you."

Lorelai stuck her tongue out at him.

Luke walked by the table with an ordering pad. He saw that there were now two coffee cups in front of Lorelai. "I thought you said the coffee was for Jess."

The mother and son shared a look and started laughing.

Lorelai was working at the Independence Inn when she received the letter that changed everything.

It was a simple enough letter. The envelope was standard size and white. The address on the front was typed instead of handwritten. The stamp was of the Liberty Bell, so much unlike the kinds of stamps Lorelai typically used to mail letters: Spice Girl collectible stamps.

The name on the return address caught her eye: Chilton Preparatory. It was the private school she had applied Jess to a few weeks ago. Unfortunately by the time they applied Chilton was full. Jess was put on a waiting list, though due to his grades and test scores they were considering bumping him to the top of the list. Still, there was a chance that an opening would never come. Lorelai had all but given up hope on her son's chances for private school.

With a pounding heart Lorelai haphazardly tore open the envelope, ripping it down its sides. The letter inside was still in pristine shape. She yanked it out and unwrapped it from its one-third fold.

Dear Ms. Gilmore, the letter said. We are happy to inform you-

Lorelai squealed and jumped up and down. She didn't need to read anymore. It was obvious what the letter said. Jess was in.

The patrons of the inn turned to look at her. Lorelai had to remind herself she was a manager. That was not how a manager in hospitality acted. She smiled, waved, then laughed.

"Hi, how ya doing? Enjoying your stay?" She tried to play off her behavior as no big deal.

Slowly the patrons went on their way, and Lorelai went back to reading the letter.

We are happy to inform you that we have a vacancy at Chilton Preparatory starting immediately. Due to your son's excellent credentials and your enthusiastic pursuit of his enrollment we would be happy to accept him as soon as the first semester's tuition has been received.

Jess did it. He got into Chilton.

"Michel." She turned to her snooty French concierge.

"Whatever it is, non," he said in his thick accent.

"But you don't even know what I'm going to say." Lorelai pouted but Michel wouldn't look in her direction, not that it would have had any effect on his stone-cold heart.

"You're going to make me deal with people and I already told you: people are too stupid for me today."

"Says the guy who works in hospitality. People are your job. Who's the real dummy now?" Lorelai picked up her purse from under the desk. "You're in charge for the next few hours." She hurried away before Michel could argue anymore.

Good news always deserved gifts, and gifts were a great excuse for shopping. At least that's what Lorelai told herself when she found herself in a department store in the middle of the day. Back when she still thought Chilton was a long shot she started searching for Chilton approved clothing to match their uniform policy, and was picking them up now. She would still need to order a blazer with the school's crest directly from the school store, but at least she would be able to give something to Jess when she delivered the good news.

Once everything was bought Lorelai sent a page to Jess, telling him to meet her at the inn after school, and went back to the inn. She couldn't contain her excitement any longer. Even if Jess was going to show up in just minutes, she knew she wouldn't be able to wait that long. She needed to tell someone now. She needed to tell her best friend. Lorelai found herself running through the lobby like a child running off to play a game.

She entered the kitchen just in time to watch Sookie wallop one of her assistants with her skillet. Lorelai checked him out but he seemed to be fine. It was an occupational hazard of working with the adorably klutzy chef Sookie St. James.

"Sookie! It's here! It happened! He did it!" Lorelai said, more like babbled.

Sookie asked Lorelai to calm down and speak in complete sentences.

"The Chilton school! Jess got in!"

Sookie and Lorelai squealed and hugged each other.

"I was so worried," Lorelai said. "I thought it was such a long shot. I knew he had the grades to get in. And he definitely has the smarts. He absolutely nailed their intake tests. But he's been in so much trouble lately and I was scared that was going to ruin his chances."

The trouble she was referring to was a suspension at the end of last year's school term. There were some other things, like fighting and disobedience too. In fact, all the trouble he'd been causing lately was the reason she wanted him going to private school.

"I know he's only getting into trouble and pulling pranks because he's bored and unchallenged. But convincing the school of that? Oh boy!"

"They must've seen his potential." Sookie waved jazz hands in the air.

"And he has so much. This is going to get him back on the Harvard path."

Lorelai couldn't remember a time when the plan wasn't for Jess to go to Harvard. He had always wanted it, ever since he was a child and she bought him his first crimson Harvard sweatshirt. He was so small at the time that it fit him like a dress. Jess had lost focus on the dream in the past few years, though. A prestigious prep school would get him back on track.

"He can get the education that I never got and do the things I never got to do and then I can resent him until he buys me a nice condo to retire to in Florida."

Sookie giggled and clapped her hands. "Hmm, sounds nice."

"Mom?" Jess entering the kitchen through the back doors.

Lorelai and Sookie shared a look and turned to greet him. Their giggles settled into wide smiles.

"You're happy," Jess said.

"Yeah." Lorelai continued to smile.

"Ah, jeez, whatever, or whoever, you did I don't want to hear about it." He placed his hands over his ears.

"Jess!" Lorelai said, half mortified that he would think that and half amused by his mortification. She tapped his shoulder and handed him the bag. "Here."

Jess pulled out a navy blue sweater vest and his forehead wrinkle. "Is this because of my Metallica t-shirt with the vomiting skull?"

In a rare role reversal, Lorelai was the one to scowl as her stomach flipped. She had forgotten about that shirt. "I thought I told you to throw that out."

"I hid it on the bottom of my dresser for a rainy day when you pissed me off. Or when you tried to dress me up like a mathlete, apparently."

Boy did this kid know how to take the joy out of a fun gift. "The sweater is for Chilton. You got in!"

Jess dropped the bag and vest onto the floor. "What?" His voice was flat.

"You did it! You got in."

"How…" Jess's eyes opened wide in shock. "The principal?"

When they had applied for Chilton months ago Lorelai told him she would sleep with the principal to get him in if she had to.

Lorelai laughed. "No, honey, that was a joke. They had an open spot. You start on Monday."

"Really?" Jess asked. His voice was slow and hesitant, instead of upbeat and excited like it should have been. Was he not happy with this news?

Lorelai smiled through his apprehension, hoping her joy would catch on. Maybe the news was taking time to sink in for him. His life was about to change. "This is a good thing. This is what we always wanted. It's your path to Harvard. Remember how much you want to go to Harvard?"

Jess picked the bag and vest back up and stared blankly at it. It was still so hard to gauge what he was thinking.

"Whatever," Jess said. He left the room without another word.

Lorelai's smile turned into another scowl. "Um, aren't you supposed to, I don't know, react when hearing news? Any sort of reaction. Happy? Sad? Hungry? Feel a freaking emotion, Jess!" she yelled at the door.

Sookie picked up a bowl and started mixing. "Oh, you know how he is. He's not a 'wear your heart on your sleeve' kind of guy. He's reserved. Quiet. Stoic, even."

"But this is huge," Lorelai said. She gestured wildly in the air. "Life changing...and...nothing. Just a 'whatever.' Well, whatever to you Jess. I don't care."

"You totally care."

Lorelai sat down, pouting now. "I totally care. I just want him to feel something."

"Anger!" Sookie said. She pumped a fist into the air.

"What?"

"Jess feels anger. A lot. Boys got one pair of lungs on him. Learned his ranting skills from you I presume."

Lorelai crossed her arms. She glared at the doors Jess had just walked through. Why did Jess have to ruin this with his bad attitude? "Ranting is the only time I ever get complete sentences out of him. The rest of the time it's just monosyllable huhs and yeps and nopes," she said.

She prayed Jess would return through those back doors with the realization about how great this life-changing news was, but as the minutes ticked by Lorelai realized she wasn't going to get the celebration she wanted. It would be okay. Jess would come around and learn to be happy with this new arrangement.

Jess stood in front of his school locker and took a deep breath. This would be the last time he opened this locker. The last time he stood in this hallway. Jess never considered himself a sentimental person, not like his mother, but he felt it today. It wasn't that he liked Stars Hollow High or would miss it—the work was too easy and he often felt like he was surrounded by morons—but it was comfortable. It was familiar and had built-in safety nets. He had no idea what to expect at Chilton.

There were numerous novels spilling out of the locker. Most were books he had already finished since the school year started. A few were ones he was still working on or were planning to get to. His textbooks had already been returned to his various former teachers.

A cardboard box sat next to Jess's feet. He dropped his things into it, one by one. When Lorelai told him to bring a box to pack his things in, he thought she was exaggerating. He didn't think he would have so much stuff. But he just kept piling papers and books and little mementos into the box. It was nearly filled to the brim now.

"Isn't it a little early for spring cleaning?" Dave Rygalski asked. Jess hadn't noticed him approach.

Jess and Dave had been friends since middle school. He was basically Jess's only continuous friend, his best friend if Jess was being sappy. Jess wasn't sappy.

Jess bent over the box as he neatly arranged the books. He didn't want them getting bent.

"I'm leaving," he said and stood up.

He pulled off the pictures taped to his locker. There was a five by seven poster of Jack Kerouac above his Offspring stickers, which were seared into the locker. He was careful to peel the poster off the locker, making sure not to tear its edges, and placed it neatly on the top of the box. He didn't bother attempting to pick the stickers off.

"I don't think you need all your stuff to go home for the night." Dave bent over and picked up the picture of Kerouac. "Unless you're working on your Beatnik collage."

Jess snatched the picture back and put it back in the box. His locker was nearly empty now except for his jacket. He put that on, then slung one strap of his backpack around his shoulders, lifted the box and kicked the locker door closed with his foot.

"I'm leaving school," Jess said. He headed for the nearest school exit.

Dave immediately followed. "What do you mean?" he asked while opening the door for Jess.

"I mean I don't go here anymore." Jess walked down the steps of the entrance of the school. A few classmates Jess never spoke to were sitting on them, talking. They moved slightly to make room for Jess and Dave to walk by without tripping. On the lawn a group of guys were tossing around a football.

"What do you mean you're not going here anymore?" Dave asked.

"Don't know how I could make it any clearer. Packed up my stuff. I'm leaving." Jess looked up at the sun. It was awfully bright, but it didn't do much for the current cold snap they were in.

Dave continued to follow Jess. "Why do I get the feeling that Miss 'My Son Is Going to Go to Harvard' isn't going to be okay with you quitting school?"

"I didn't say I was quitting school. Just leaving that one. Got into that prep school Mom made me apply to."

Jess wasn't sure why he was giving Dave so much attitude. Maybe picking a fight with him was just easier than leaving behind his best friend. He walked toward Luke's and attempted to quicken his pace but Dave easily kept up. He wasn't the one carrying a heavy box.

"Then why didn't you just say that in the first place? You had me worried you were doing something crazy and stupid. Not that that would be out of character for you."

Jess stopped in the middle of the street and turned toward Dave. His expression had transformed into a scowl. "Would you just stop harping on this? I don't want to talk about it. Lorelai didn't ask me if I wanted to go to another school. She made the decision for me. Just like she always does. Because she pretends to be the cool mom, and as long as you go along with every single tiny demand she has she's your friend, but as soon as you try to carve your own path she plays the mom card."

That wasn't fair to Lorelai and Jess knew it. She was only trying to help him, and they both knew if he stuck around at Stars Hollow High, unchallenged and bored, he would get himself into more trouble. Last year was a handful of detentions and a suspension. What would happen this year if Jess stuck around at this school?

A car drove toward the two. It honked but the two teens didn't move. It honked again as it maneuvered around them on the street. Dave fidgeted, but when Jess stayed put and didn't make a move towards the sidewalk neither did Dave.

"Your mom just wants what's best for you," Dave said.

"My mom just wants what's best for herself." Again, Jess was saying things he didn't necessarily believe. Why was he being so hard on Lorelai?

Jess started walking again, and this time Dave didn't follow. Jess changed directions and walked home. He had planned to meet Lorelai at Luke's so she could drive his stuff home instead of making him lug it around town, but now he didn't much care to see her.

Lorelai and Jess sat across from each other in silence at a table in Luke's. Jess was particularly moody lately. Technically, he had been moody since he turned thirteen, but the last twenty-four hours he had been worse than usual.

If that wasn't bad enough Lorelai was dealing with her own problems. She couldn't afford Jess's tuition. She had racked her brain for ideas to fund him but the only idea she could conceive was something she had promised herself she would never do. The only way Lorelai could afford Jess's tuition was asking her parents for the money, so that afternoon Lorelai sucked up her pride and visited her estranged parents. Her parents, millionaires who raised and suffocated her with false love until she ran away, were just as cold and uninviting as she remembered. She told them about her situation and they agreed to loan her the money, but only if she agreed to the following one condition: weekly Friday night dinners.

It was horrifying. Lorelai spent her whole life trying to escape them and with one swoop they were back. She traded her freedom for Jess's education. Jess was worth it, though. She always did what she had to for her kid.

Jess continued to sit in silence, just staring at the table while they waited for their burgers. Lorelai had stolen his book again, but instead of lightening the mood and forcing him to talk to her it only pissed him off and further drove a wedge between them.

Well, Lorelai had to slip the news in at some point. She would have to bring Jess along with her to the dinner, after all.

"Oh, I forgot to tell you. We're having dinner with your grandparents tomorrow."

That got Jess's attention. He looked up with his trademark scowl.

"But it's September."

"So?"

"So what holiday is in September?"

"It's not a holiday thing. It's just dinner."

Jess opened his mouth then closed it. He shook his head. "Whatever."

Luke came by and served their burgers. "Red meat can kill you," he said. "Enjoy." Well, Luke was as charming as ever. Lorelai picked up her burger and took a bite.

"I don't understand why we're going to dinner tomorrow night. You hate your parents."

"I do not hate my parents."

Jess mumbled something incomprehensible under his breath.

"Yes, I have issues with my parents," Lorelai said.

God knew she had issues. Her mother, Emily, was the more controlling parent; Lorelai was expected to live up to a certain standard and when she inevitably fell short Emily would passive-aggressively shame Lorelai. It was Emily's idea to institute Friday Night Dinners. Her father, Richard, was cold and distant. Growing up he would go to work, come home, have dinner and then go to bed. If she was lucky he might ask her how her day was. Most nights she wasn't lucky. That house was a nightmare, and that was why Lorelai left as soon as she could. It was why her parents were barely involved in her adult life or with her kid. Things were about to change, though.

"But I tolerate them," Lorelai added.

"Well, that's very loving of you."

Lorelai glared. She was sick of this attitude. Dinner would be hard enough without Jess's backlash. "I will not have you mock my relationship with my parents. You of all people should know what my issues with them are."

Jess banged his fist against the table. It shook and the silverware upon it clattered. "Then why the Hell are we seeing them?"

"Because!"

"Great reasoning." Jess picked up a fry, stared at it, and then dropped it back on the plate. He still hadn't touched the burger.

Lorelai felt like she had been slapped. She was used to Jess giving her a little attitude, but this was a new level. "What the Hell is your problem Jess? You've been in this funk since yesterday."

Jess rolled his eyes but didn't answer.

Lorelai leaned across the table and reached out her hand. She touched Jess's forearm. Clearly there was something deeply wrong with her only child and she needed to fix it.

"Tell me what's wrong," she said.

Jess pulled his arm away. "Leave me alone." He stood up and stormed out of the diner, without having taken a bite of any of the food.

Lorelai sat with her mouth agape for a moment before collecting herself. She left money on the table for the burgers then chased after Jess.

"Jess! You do not just take off in the middle of us talking."

Jess turned his head back while still plowing forward. He walked by Patty's Dance Studio as she counted off beats for her dancers. Patty continued counting the beats, but at a quieter volume, obviously listening to the scene unfolding right in front of her.

"You were talking. I just wanted to eat my dinner," Jess said.

"You need to talk to me," Lorelai said. "We used to talk. Why don't you talk to me anymore?"

"Because I'm not ten. I don't need to go to my mommy for my problems anymore." Jess continued walking, out of earshot of Patty. Lorelai caught up with him and grabbed his arm. He easily slipped out of her grasp.

"This whole 'the world can bite my ass' shtick is going to get real old real fast. In fact, it already has."

"Thanks for the insight, Dear Abby." Jess quickened his pace, and Lorelai found it impossible to keep up with him in her heels. Jess reached the house first. He slammed the front door behind him. By the time Lorelai entered Jess was already in his room.

Lorelai took a deep breath before she opened Jess's door. She needed to be the calm, rational one. Them both screaming at each other would not solve any problems.

Jess was already sitting on his bed, with As I Lay Dying in his hands. Lorelai hoped he didn't choose that novel because of wishful thinking.

"I'm your mother," Lorelai said, her voice calm and soothing. "I'm here to help you, guide you, find solutions to your problems."

Jess peered up from his book and glared. When Lorelai didn't leave and instead took a seat at the edge of his bed Jess put the book down and leaned forward.

"You don't get it. You are my problem."

"Me? What did I do?" Lorelai felt a lump in her throat. Sometimes Jess could be too mean.

"Forget it." Jess leaned back on the bed, propped up by only his pillow.

"No, tell me what the Hell I did to piss you off so much and put you in such a foul mood." The anger was back and there was nothing Lorelai could do to starve it off again.

Jess rolled over to his side, breaking their eye contact. "It doesn't matter if I talk to you about it. You never listen to what I have to say." He turned back up at her for say his final words of the argument. They cut the air like knives. "You're just like your mother."

The room spun and Lorelai got a terrible case of vertigo. She wanted to run out of that room, for Jess not to see her cry, but she couldn't get onto her feet. How could Jess say such a terrible thing? He knew her relationship with her mother. It was like he was trying to hurt her.

Lorelai concentrated on her breathing and wiped her eyes. Finally, the equilibrium was restored. She didn't say another word to Jess. She just walked out of his room and slammed the door behind her. She waited until she reached her own room to let out the sobs.

By Friday the ice between Lorelai and Jess still hadn't thawed. Jess skipped his daily breakfast at Luke's with Lorelai, and then ignored her after school. Once they arrived at the Grandparent's house for dinner, Lorelai's apprehension of entering wasn't helping the situation. She had dragged Jess against his will to Hartford on a Friday night but was now refusing to ring the doorbell. She just stood outside the manor sipping her coffee.

"So, do we go in or do we just stand here reenacting the Little Match Girl?" Jess asked.

"Okay, look, I know you and me are having a thing here, and I know you hate me but I need you to be civil," Lorelai said. "At least through dinner and then on the way home you can pull a Menendez. Deal?"

Jess gave a non-enthusiastic nod. Finally, Lorelai rang the doorbell. Emily Gilmore opened the door. She smiled. Neither of the younger two Gilmores said anything.

"Well, you're right on time," Emily said.

The last time Jess was at this house was last Christmas. The holidays were the only time the family ever got together, and only ever at this house during Richard and Emily's parties. His grandparents had never been to Stars Hollow.

As Lorelai and Emily made small talk and argued over where to throw Lorelai's coffee cup Jess hesitantly walked into the house. He had never been alone in the house with just his mother, grandparents and their staff before. It made the place seem even larger than usual. Jess loosened the tie Lorelai made him wear.

Emily caught up to Jess and grabbed his arm, looping her own around it. He nearly jumped out of his skin at the touch. He didn't like to be touched, and even less so when he wasn't expecting it. "I want to hear all about Chilton," Emily said.

Jess sighed and attempted to do his best Stepford impression. He most likely fell short but Emily didn't seem to mind. "Haven't started yet."

"Richard, look who's here," Emily said as they entered the living room. Richard was sitting on a sofa reading a newspaper. Glasses framed his face.

Richard peeked up from his paper. "Jess." He looked the boy up and down. "You've grown."

"Puberty's been kind," Jess said.

"Still growing?"

Jess shrugged and took a seat on the couch across from Richard's.

"Jess," Emily scolded. "Your grandfather asked you a question." She was at the drink cart.

"I don't know," he said through his teeth. What a ridiculous question. He wasn't a doctor. He didn't spend his evenings making height predictions on charts.

Lorelai joined the room. She took a seat on the couch next to Jess.

"Well, your mother's tall," Richard said. "And your father's tall. You'll probably be tall." He went back to reading his newspaper and didn't say another word until dinner.

"Thanks for the anatomy lesson," Jess said under his breath.

Emily walked over with a tray of drinks. "Champagne anyone?"

Lorelai stood up and took a glass. "Oh, that's fancy!" She sipped it before they even did a cheers.

Emily handed a glass of a slightly different color liquid to Jess. "Sparkling apple juice," she said.

"Fun," he muttered. Everyone else would be able to drink away their miseries about being stuck at this awkward dinner, but not him. He was fifteen so he had to suffer.

"What did you say?" Emily asked as she passed the last glass to Richard.

Jess cleared his throat and put on a fake smile. "I said 'thank you!' " These people were really starting to grate his nerves. At least when Jess and his mother came over for holiday parties the attention was spread out. He was usually able to slip away unnoticed and hide in his mother's old bedroom. There would be no hiding tonight.

After a little more chit-chat and drinks, during which Jess tried to avoid the conversation and answered direct questions in only monosyllable responses, dinner was ready. As they walked to the dining room Lorelai pulled Jess aside.

"Hey, I thought you agreed to be civil," she said. She had already drunk a martini in addition to her champagne and Jess could spy from his spot in the hallway a wine glass in front of her plate. It must have been easy for her to judge his poor attitude from way up there on her tipsy high horse.

Jess glared at her. "This is me being civil. I'm sorry that I don't have the good-hearted nature of Opie but this is me giving a genuine effort."

"If this is you nice, I'd hate to see what you're like when you're actually trying to be a jerk."

"Maybe you'll see on the car ride home," Jess threatened.

"Hey that Menendez offer was a joke."

Emily walked back toward Lorelai and Jess, immediately shutting up the younger two Gilmores. Condescension dripped off Emily's voice. "You know, we all got up to go eat dinner together?"

"Yes, I know mother," Lorelai said. She looked down at her feet.

"Would you like me to send the food back and for your father and I to go back to the parlor for another drink?"

"No mother. We're coming."

"I don't see why you two couldn't have had this conversation before dinner. We were all in the parlor together and you two barely said anything. Why is it suddenly so important to talk now? Why can't this conversation be had at the dinner table?"

Lorelai sighed and marched into the dining room. Jess meekly followed, avoiding eye contact with either grandparent. He didn't want to incur anymore of his grandmother's passive wrath.

Emily smiled to herself and strolled back to her seat. She unrolled her napkin and placed it delicately on her lap. "Ah, finally we're all here. Now we can have dinner at last."

Dinner was filled with mostly awkward silence. Lorelai and Jess were still in a tiff and not talking. Emily tried to engage Jess in conversation, but he wasn't biting. Richard spoke even less than Jess. Lorelai's contribution to the conversation was only cracking jokes. Emily's attempt at small talk about the food failed miserably.

Jess just wanted to eat in peace and leave. He still didn't know why they were even having dinner here.

Eventually, Jess's father was brought up. Jess learned a long time ago that following Christopher was usually hurt feelings and tears.

"He was always a smart one, that boy," Richard said. "You must take after him."

The room suddenly went tense. How dare Richard compare Jess to the man who abandoned him? As Jess glared at his grandfather he thought about how nice it would be to be a Kryptonian. If there was ever a need for heat vision.

Jess didn't get the chance to tell off his grandfather. Lorelai left the table in a huff first, reminding Jess of the fact that he wasn't the only one Christopher abandoned.

The three remaining Gilmores sat in silence. Richard went back to eating his lamb, but Jess and Emily exchanged glances at the door. Finally, Jess stood up from the table.

"Where are you going?" Emily asked. She stalked Jess out of the room when he went to find his mother.

Lorelai was in the kitchen, washing dishes. If it wasn't so sad the sight would've been amusing. Lorelai didn't even do the dishes at their own house. Dirty dishes were part of the reason she hated cooking. Emily and Richard must have really pushed a button.

"Lorelai, come back to the table," Emily said.

Lorelai threw the plates into the sink. They clattered and from the sound of it may have even broke. She turned around, her eyebrows pinched and nose flared, but the expression soften when her eyes landed on Jess. "I'm not having this out right now," she said.

Jess leaned against the kitchen island. This night had turned into a shit-show. He couldn't tolerate it anymore and a small part of him wanted to shield his mother from any more upsetting comments. "Can we go?"

Emily glared at him. Apparently, the glare was a family trait. She turned back to Lorelai. "If you leave before dinner's over you're not getting-"

"Don't say it!" Lorelai shouted.

Jess looked between his mother and grandmother. They were talking in code. They had some sort of secret between them. "What's going on?" he asked slowly, trying to figure it out on his own. What would lead to a random dinner in the middle of September? Were there any extenuating circumstances? Any recent changes in their lives? Jess tried to calculate all possible reasons.

"Nothing," Lorelai said. "Go back to the table," she said.

Lorelai should've known better than to think Jess would just listen to her commands, not when he was curious. He was going to keep picking at this until someone broke.

"Are you two in cahoots?"

No one answered.

"Grandpa's dying and you're scared of being cut out of the will? You and Sookie are finally going to open an inn of your own and need a loan? You're pregnant and need a full-time babysitter?"

"Shut up Jess!" Lorelai screamed.

Jess frowned and looked down at his shoes. Maybe that last one hit a little too close to home, what with the circumstances of why Lorelai had such a strained relationship with her parents.

"Maybe you should just tell him," Emily said. "He's a smart boy."

"Smart like Christopher?" Lorelai retorted.

"You father didn't mean anything by that comment. He likes Christopher."

"Oh does he? Because I seemed to remember Dad not liking Chris so much right after I got pregnant."

Emily pursed her lips and looked at Jess. "Let's not talk about this right now."

"He knows he's the product of teen pregnancy, Mom. I've never hid my past from Jess."

Jess felt cold. This was exactly the fight he hoped to avoid. He didn't need to be reminded of how unwanted he was and how his existence ruined everyone's lives. He wanted to run before this argument could occur, but it was too late now.

"Well, I'm glad you have standards. I'm glad you and Jess have no secret." Emily's words dripped with sarcasm. Jess tried to avoid his own self-loathing by wondering about the secret Lorelai was keeping from him. "It's certainly a relationship I always aspired to have with my daughter," Emily continued, "but I guess we can't all be that lucky with our children." Emily stormed out of the room.

Jess looked at his mother, pleading with his eyes that she would tell him the truth about tonight's dinner.

Silence hung in the room instead.

"If you're not going to tell me I'm leaving," Jess finally said. "I'll see you in the car." He headed for the door.

"Wait." Lorelai bit her lip. She breathed in and out a few times. "I couldn't afford Chilton."

Jess turned around to face his mother and put his hands in his pockets. "That's okay. I didn't really want to go."

Lorelai shook her head. "You need to go. I know how unchallenged you are at Stars Hollow High." She crossed the room and put her hands on Jess' shoulders. He flinched, but she kept them there anyway. "You're so smart, you know that. I know all mothers think their kids are smart, but you just amaze me. You need a school that can keep up with these brains." She ruffled his hair.

Jess swallowed and noticed how dry his throat was. "Not a big deal. Don't worry about it."

Lorelai stomped her foot. "It is a big deal…that's why I came to mom and dad. I asked for a loan."

"What?"

Lorelai never took any help from anyone. She was a self-sufficient woman. She literally called herself by that exact phrase just the other day.

"And part of the deal is Friday Night Dinners."

There was silence again. Jess mulled over the idea. The whole reason Lorelai put up with this dinner, and was willing to put up with more, was for him? It made his head spin. As much as he hated the dinner he knew it was ten times worst for Lorelai. How could he act so spoiled and throw this gift back in her face when she was willing to sacrifice so much for him, including the pride and independence that she so dearly treasured?

"Dinners? As in plural?" Jess asked.

"Yeah. Every Friday night until…well ever, I guess. Or I cough up enough to buy myself out of this Devil's contract."

"Okay," Jess said quietly.

"Huh?" Lorelai asked.

"I know it was hard for you to go to them but you did it for me. So…I'm grateful for that, at least."

Lorelai pulled Jess into a hug and rested her chin against his shoulder. "You're the best kid ever, you know that?"

Jess squeezed his mother back. Normally he hated hugs, but times of vulnerability were the exception. Sometimes you just really needed the closeness of another.

"You okay?" Jess asked when the hug ended.

Lorelai wiped her moist eyes, smudging her eyeliner. "I really don't want to talk about this."

"Ironic, huh? You being the one to not talk?"

"So you'll go?" Lorelai asked. "To Chilton?"

Jess wondered if it was time to break the tension with a joke. Probably not. "Yeah, I'll go."

Lorelai smiled and stroked his cheek. "You're going to do great. A mother knows these things." Her eyes flashed to the door. "Shall we venture back into the Dark Side Cave?"

Back to the psychological torture that was Grandma and Grandpa—would they continue to pick at all of Lorelai and Jess's insecurity? Would this continue to last for, well, however long it would take Lorelai and Jess to pay back the loan—it didn't seem like they had much of a choice. Jess squeezed his mother's hand for reassurance and then walked with her back toward their tormentors.

A/n: Thank you for reading and I hope you liked my story.

I wanted to take a moment to explain how this story came into existence and what you should be expecting from it in the future. I originally got the idea for this story twelve years ago. I even published a very different version of the story on my old account. It was super edgy and not good and I deleted it.

A few years ago I started rewatching Gilmore Girls for the umpteenth time, and the idea came to me again, so I did a complete rewrite. Basically, all I kept was the premise. It became a real in-depth story about lives and relationships between Jess, Rory, Lorelai and Luke. This story has everything, from family relationships to romance to teen angst to parenthood woos.

I've kept everyone's personalities mostly intact: Jess is still surly and anti-social, Rory is still kind and Bambi-like, but now Jess and Rory must go through the events of each other lives and see how their own personalities would react to each other's trials and tribulations.

This story is going to be long and take place over the course of a year. As you may have noticed Rory didn't appear in this chapter, but she'll have a large role starting in the next chapter. Luke takes a while to get more significant, but he will be soon too. While romance has a large role in the story, the platonic relationships between friends and family are the real drive. For those shippers out there will be multiple love triangles involved Rory, Jess, Paris, and Tristan. Lorelai's romances will be a little more subtle but a romance with Luke, Chris or Max are all possible. I'm not revealing my endgame couples yet, though.

There will also be some heavy topics and themes explored, but any and all upsetting content will be warned at the start of those chapters. The dark themes are balanced with a good dose of humor that fits the tone of the show.

I'd also like to take a moment to thank all the people on the r/fanfiction Discord server for all their help with writing this story. They helped me not only with my ideas but also with the finer technical details of writing. They're awesome people and I one hundred percent recommend them and the r/fanfiction subreddit.