A/N: Jess flashbacks are coming! Just thought I'd share haha XD

"Oh my god," Rory laughed. "Really?"

"I'm dead serious," Jess laughed, too but tried to say his words as serious as possible to prove his point.

"He wore a maid uniform?" Rory asked. "Just to clean Truncheon?"

"Yep," he popped the 'p'. "I tell you, Matt can be ridiculous when he...no, scratch that. Matt is always ridiculous."

She took a sip of her drink and laughed again. It felt so easy to get back to the friendship part of them. It just felt easy being with Jess at all if she was being honest. "Please tell me you have pictures."

Jess took his phone out of his pocket and pressed the screen a few times before pushing it towards Rory. "Here you go."

"Oh my god," she repeated, laughing harder. "Look at him! What a set of legs!"

"Ssh," Jess held a finger over his lips. "He can't hear that. A beautiful girl looks at his legs...who knows what will happen?"

"In my defense," she pushed the phone back and Jess took it. "You showed me the picture."

"Fine, whatever you say," he smirked and took another swig of his beer.

She smiled at him. "I like your friends."

"Why?" He snorted as a joke. "You don't know how annoying they are."

"I met them!" She exclaimed in defense.

"For a couple of seconds during one of our busiest nights," he recalled. "That's when they're on their best behavior. Of course you liked them."

She scrunched her nose and made a face at him. "So? I still like them."

"You would," he smirked.

Rory gasped. "What does that mean?"

"You live in Stars Hollow," he pointed out with a look. "You'd like anyone."

"Hey!" She defended. "First of all, I'm a big Apple girl now."

Jess laughed. "Right."

"And..." she drew out the word then continued. "No making fun of my town!"

"If New York City isn't my city anymore, then Stars Hollow isn't your town anymore," he pointed out.

"I grew up there!"

"So did I!"

Rory pouted, stuck on her next words because she didn't have any. "Fine. Truce?"

"Didn't know we were fighting," he smirked. "But, yeah, truce."

She nodded, a smile on her face. "Thank you."

"So what about your friends?" He asked. "Do you still talk to people you grew up with?"

"Paris and Doyle got married," she told him. "About...seven years ago."

"Doyle?" He asked.

"Right," she said. "You two never met. They met freshmen year at Yale, didn't date until sophomore year. Well, not date so much as slept together and I happens to come by afterwards."

Jess laughed. "Scale of awkward?"

"Very," she nodded with a laugh. "And that wasn't the worst time I've caught them."

"I'm intrigued," he commented. "What other stories are there?"

"Another time," Rory said. "I'm not drunk enough to relive those memories."

"Another time," he repeated. "What else?"

"Lane had a baby girl," she answered. "Christina."

"Wow," he said and drank more of his beer. "When was that?"

"About six months ago," she answered. "Lane swore she'd never have any more kids after the boys. But then she got pregnant again. Her mom watches her a lot, which is good despite what you'd think."

"It's still weird to believe Lane is a mother," he said.

"Oh, I know," she agreed. "If you asked me back in high school who I'd thought be married with children first of the two of us...I wouldn't have guessed her."

"Mrs. Kim lightened up, I guess?" He asked, steering away from that look in her eyes he could only guess was thinking about her divorce.

"A lot," she nodded with a slight smile. "She didn't even have a panic attack when Lane told her about the twins or Zach asked if he could marry Lane."

"Wow," he nodded too. "She sounds more mellow, now."

"Oh, don't be fooled," Rory replied in a serious tone. "She's still the same, just...softer, I guess is the right word."

"Wow," he repeated. Rory gave him a look as if she wanted to say something but didn't. Jess noticed. "What?"

"Remember when you came to Lane's window to see me?" She laughed.

"The baseball bat," he remarked with his own laugh. "I thought she was going to beat me with it."

"She probably wanted to," she teased. "You ran out of there so fast!"

"Scary woman plus a baseball bat..." He said. "Not exactly a fun situation."

She just laughed again. "It was funny in my end."

"That's because she likes you," he pointed out.

"Maybe," she said. "But she didn't approve of me having a boyfriend without marriage plans, especially a bad boy, James Dean boyfriend."

He smirked. "If she had problems with you, I can't imagine what she actually thought of me."

They each took another drink and realized they were down to the bottoms of their glass and bottle. Jess ordered another for both of them and when the waitress walked away, Rory spoke again. "I wanted to come out with you that night, you know."

"What?" He questioned after taking the last sip from his old beer.

"You asked me about getting out of there, remember?" She teased. "Come on. Don't tell me you forgot."

"I didn't forget," he answered. "Thought you might have."

"No," she said softly. "But I was about to answer before Mrs. Kim came..."

He nodded. "Huh."

He took another drink and peeled at the label. Rory watched him, curious then took a sip of her own drink for more courage. "What are you thinking?"

Jess' gaze turned to her and his eyes were thoughtful, soft. "I screwed up a lot back then, didn't I?"

"A little," she answered. He gave her a look that told her not to lie. "Maybe a lot."

"I am sorry about all of that," he told her. "I never told you that."

"I know," she referred to his apology.

They were quiet a moment and Rory didn't want the night to turn awkward all because she mentioned something in high school. She searched for something that would change the tension and hopefully take it away.

"My mom told me you snore," she chuckled.

"What?!" Jess almost spit out his drink. "How would she know anything about how I sleep?"

"That night of the Inn fire," she replied as if that answered all. "Mom stayed in Luke's apartment."

"Right," he thought back to that night and remembered seeing her in Luke's bed when he noticed his uncle on the couch. He was thinking about how Rory didn't get to answer and how beautiful she looked even in her pajamas when he realized her mother was in his home.

Rory laughed, remembering it herself. "She said it so casually like she read it book. 'Hey your boyfriend snores, by the way' - exactly what she said."

He laughed. "What did you say?"

"How I didn't need to know that," she smirked. "But maybe I did."

"Why?" He smirked back. "Were you planning on being around when I sleep?"

She blushed, looking down at her hands. He smirked bigger, watching her expression before Rory finally looked back at him. "Maybe I was planning on killing you in your sleep and needed to know how sound a sleeper you were."

"Ouch, Gilmore," he held his hand over his heart in mock-hurt. "You wound me."

She laughed and drank some more of her drink, shrugging. "I guess you'll never know now. Not as easy to plan a homicide from New York City to Philadelphia."

"True," he agreed. "There's no poor defenseless men in New York City to come after?"

"How do you know it's guys only?" She leaned forward with a teasing look on her face.

Jess just stared at her, trying to read her expression. "Well, that would be really...hot."

Rory laughed, leaning back to her previous position in her seat. He pouted at her which only make her more entertained. "You so like that idea, don't you?"

He shook his head in denial. "No...not at all."

She grinned then gasped. "Speaking of! Did you know Paris kissed me?"

His eyes almost bugged out. "Paris Gellar?"

"Yep."

"Crazy, Chilton Paris?"

"That's the one."

Jess let out a low laugh. "Now this I need to hear."

...

Jess sat at a bar in Philadelphia on a Saturday night. Actually it was more like morning at this point. He finished off another glass of whiskey. It wasn't his usual drink - Jess was more of a beer guy - but he wanted something different. The usual things he liked weren't cutting it tonight.

The bartender came around again and he asked for another. She looked at him curiously but instead of saying anything, she just gave him another whiskey. Jess sat there, seething as he recalled the nights events. Hell, even the day's events.

Rory had came to see him for the first time since after the accident. He would give anything to be back there instead of how he felt right now. Everything with Dean didn't even feel like it compared to hearing her say she was in love with the blonde dick. She had never told him she was in love with Dean to his face, not the way she said she was in love with...him.

His new glass was done in seconds and he asked for another. Jess was already drinking it by the time someone came and sat beside him. He didn't look at the person, figuring it was nobody important. Then he heard a familiar voice. "I thought you didn't want to go to a bar tonight."

"Changed my mind," he told his friend.

"Was it the girl?" Chris asked. "The one who was there tonight?"

Jess nodded. "Yep. It's always her, it seems like."

Chris ordered his own drink then turned to Jess. "Do you want to talk about it?"

"Not really," Jess snorted.

"Let's get you home," he told him. "Come on."

"Not yet," Jess' disagreed. "I'm not drunk enough to forget today yet."

"You mean yesterday?" Chris asked teasingly, trying to help his friend's mood. Judging by the look on his face, it didn't have the desired effect.

Chris finished off his drink, tossing his head back to get it all then stood up. "Come on, Jess. Let's go."

Jess shrugged off his friend's hand, groaning. "I'll leave whenever I'm ready."

"Jess..." Chris pleaded.

"She came here to use me," Jess started, anger coming out of his words. "After all of our history, I made a friendly gesture to her. To invite her to something that only was possible because of her. And this is what she does."

"She used you?" Chris asked, surprised. He remembers seeing them talking earlier. Jess was actually smiling and happy and she looked it, too.

"Tried to," Jess answered. "Her asshole boyfriend cheated on her so she came here so I could help her cheat on him."

Chris looked even more shocked. "She told you this?"

"Not in so many words," he drank some more. "But I got the gist. Nice to know I'm only good for revenge sex, though."

"Did you two -"

"No."

"Too guilty?" Chris asked, wondering if Jess went through any of it.

"I didn't know," he replied. "I kissed her and she pulled away, telling me how she couldn't cheat on the dick the way he cheated on her. Wasn't exactly a turn on."

The bartender came back and Jess got another while Chris shook his head to her. "I think you had enough."

"Nope," Jess said bitterly. "I still remember what it felt like seeing her and how it felt when she left."

"Come on, man," Chris tried to hold onto him and pull him up. "You need to sleep it off."

"One more," he whined.

"No more," his friend corrected. He finally got Jess to stand up. He helped him walk away after putting money down. "I'm gonna get you home."

Jess struggled to walk but managed only because of Chris' support. "I loved her. She's the only person I ever loved. Does she even care about me or am I just a tool for when she gets tired of her boyfriends?"

"I don't know," Chris told him honestly. "Let's just get you home and you can sleep this off and maybe feel better in the morning...besides the hangover."

Jess smirked. "Hopefully."

Chris piled Jess into the backseat of his car after Jess remembered he took a cab to the bar. He should have figured as much since he seemed like he wanted to get passed put drunk. When they got home, Matt came rushing to them off of the couch.

"What happened?" He asked as he slung Jess' other arm around him and they attempted walking him to the couch.

"He's been drinking," Chris explained.

Matt nodded as if that answered everything. "Was it because of that girl? The one who was here tonight?"

"Yep," he answered. "It's a long and complicated story, apparently."

"Five years," Jess groaned.

"What?" Chris asked.

"Five years since I first saw her," he mumbled and slurred but they understood. This was not the first time they've seen Jess drunk.

The two guys nodded together. It was starting to make sense. They got him to lay down and took off his shoes. Jess fell right asleep as soon as he was down.

...

Rory was giggling. A lot. Jess thought it was adorable and he couldn't even push the thoughts aside because he, too, was close to giggling. She waved her band in front of her face and couldn't stop her giggling.

"You're really drunk," he told her.

"You, too," she laughed.

He nodded and felt his head spin. "How much did we drink?"

She thought for a moment then laughed. "I lost count."

"Why did we drink so much?" He rephrased his question.

"I dunno," she laughed. Jess was laughing with her and he didn't even care how happy he seemed at the moment.

"I can't drive," he told her.

Rory gasped. "I could drive!"

"No, you can't," he laughed. "I need to -"

He fumbled through his pockets, cutting his own words off as he looked for his phone. Rory watches him, laughter ready to bubble out of lips. He finally finds it and checks it to see his battery is about to die.

"Damn," he laughs.

"Use mine," she said and pulled out her own phone.

Jess mumbled a thanks and took the phone from her hand, their fingers touching for a second. After what seemed like forever looking through he phone book, he found his uncle's name - he wasn't even sure how - and called it.

"Oh!" Rory gasped. "Don't tell my mom!"

"Kay," he murmered, not wanting to ask and not really being up for an actual conversation. He was bound to get enough of that tomorrow morning along with a lecture.

The phone finally picked up and he could hear his tired uncle on the other end. "Rory?"

"Guess again," Jess laughed.

"Jess?" Luke's voice was worried now. "What's going on? Is something wrong?"

"No," he said. "We need a ride."

"Where are you?"

Jess told him the location and Luke sighed. "Can you get us?"

Rory was anxiously bouncing on her feet, watching him. "Is my mom there?"

Jess shrugged while Luke answered. "I'll get you."

He was about to hang up when he called Luke's name. "Lorelai can't know."

"All right," he promised. "I'll be there in a few minutes."

They officially hung up and waited. Luke came by in fifteen minutes. Rory wobbled a little to the car so Jess tried to help her which wasn't as much help as it should have been. The older man took one look behind him at his wife's daughter and sighed. Daggers were shot in Jess' direction once Rory closed her eyes and leaned her head back.

They were quiet the whole ride and Luke dropped them off at the diner, per Jess' request. He helped Rory get upstairs then went back to his car, telling them not to do anything...stupid. Rory collapsed right down on a bed face first and snuggled to the pillow. Jess took the other bed and went to sleep, too.

...

The notebook was almost full after hours of writing and planning. Jess sighed as he finished another chapter of in his latest thoughts, wondering what else there was left to write. He even had sketch pages where he scribbled pictures of a girl holding a still bleeding heart in her hands, the blood dripping down to the ground. Jess was never particularly an artist but he really liked those sketches.

Matt knocked on the door, standing in the entrance to Jess' room. "You feeling any better?"

"Yeah," he sighed, trying to believe his own lie. "I'm not puking anymore so that's a plus."

"That would be," Matt agreed. "But I wasn't talking about that."

Jess' expression fell. "I'm fine."

"You don't seem fine," his friend explained. "First you were getting drunk and now you're hiding in your room all day."

"I'm hungover," Jess defended. Matt gave him a strange look. "Fine, maybe not anymore because I'm used to bring drunk and holding my liquor and shit like that. But I'm also...writing."

"You're writing?" He gasped. "About the girl?"

He took a deep breath. Why did he pick friends who stick their nose into his business? "A little. It's not all about her, though."

"Can I see?"

Matt leaned over Jess' shoulder, now in the room. Jess leaned away and closed the book shut. "Let me have it for a few days before you come sniffing for inspection, huh?"

"Fine," he grumbled. "I'll be downstairs, working."

He left with a pout and Jess sighed. He guessed he couldn't avoid work forever. He opened up the notebook again and saw his scratched out opening notes. Above them, he scribbled Dark? And circled the word. Then he stood up and went back downstairs to work and try to forget the previous day and why he had wanted to be drunk in the first place.

A/N: I had a hard time writing this! I don't know why. But I decided to start with the night we last saw Jess on the show and maybe counter him getting drunk over Rory vs him getting drunk with Rory. Also went a little back and forth on what would happen with drunk Lit and considered the obvious options but I hope its still good!

Plus I have another one-shot idea I'm hoping to get out by the end of the week. I've been so crazy busy lately it seems but I'm gonna try my hardest anyway haha. Thank you so so much for reading, reviewing, following, anything. You inspire me as much as Literati does which means a whole ton :)