A/N: Thank you, thank you, thank you for the reviews! They mean so much to me and I especially love your thoughts on the last chapter. I'm sorry I don't get to respond to them but know I'm reading them and they make me smile. They also inspire me to keep writing. You rock :)

Lorelai sat in the kitchen leafing through a fashion magazine and pouted. She was looking at all the cute outfits she wouldn't be fitting into pretty soon and sighed.

"Mom!"

She looked up to the room besides the one she was sitting in and saw her daughter standing in the doorway of her old room.

"Yes, hon?"

"I don't have anything to wear!" She gasped.

Lorelai looked up and down at Rory. "You looked dressed to me."

Rory tilted her head at her mother, glaring. "Not right now. For tonight."

"And you realized this by going into your brother's room and seeing your clothes are not in there anymore?" She laughed.

Rory's glare became more pointed. "Sue me. I forgot everything is officially moved out of here."

"What are you looking for, anyway?" Her mother asked. "The stuff we had here was like a couple sweaters, some jeans and your Chilton uniform. Were you planning on wearing your old school uniform?!"

"No," Rory answered as if her mother seriously asked that and not as a tease. She sighed and sat down at the table. "I just don't know what to wear tonight."

"I'm sure you have stuff in your suitcase to wear," Lorelai reassured her.

"I looked," Rory shook her head. "What is good to wear to a dinner with your ex-boyfriend? An ex-boyfriend who looks really really good?"

Lorelai almost snickered. "You've been thinking how good Jess looks?"

"Shut up," Rory smiled. "I don't know, Mom. He's just...Jess. And I feel like this is going to go bad if I don't prepare."

"Hon, breathe," she told her daughter and out her hand on Rory's arm. "If this is making you freak out this much, maybe you shouldn't go."

"You're just saying that because it's Jess," she smirked.

"Maybe," Lorelai shrugged. "But you're forgetting I see the guy more than you do nowadays. Maybe we're best friends."

Rory laughed. "You and Jess - best friends? I'd pay to see that."

Lorelai pouted. "Fine. Don't believe your poor mother. What can I do to help?"

"Do you have any nice dinner clothes I can borrow?" Rory asked hopefully.

"Please, that's all I have," she smiled, getting up from the table. "Though I won't be able to wear them for some time now."

"Clothes is all you're thinking of while carrying this baby?" Rory stood up and followed behind her mom.

"Maybe," Lorelai smirked.

...

Jess walked back and forth in Luke's upstairs apartment. He wasn't sure why be felt so nervous about tonight. It's not like he and Rory had never been alone before, not like they never went to dinner before. He then thought of how they never were alone at dinner since that night in Philly nine years ago and the nerves came back differently.

Why had he agreed to this?, he asked himself. Jess ran his hands through his hair. It was shorter than it had been back in high school but not too short. He sighed, taking a deep breath. He could always call it off, too, he knew. But there was a part of him, a big part, that didn't want to.

The door opened and in walked his uncle. Luke froze when seeing him standing there in the middle of the apartment, in front of the couch. "What are you doing?"

"Nothing," he shrugged. "Thinking."

"Rory?" Luke asked, walking more into the apartment and shutting the door behind him. Jess looked up at him with a glare. "It is her, then."

Jess sighed. "Did you ever want to see Lorelai but not want to see her at the same time? After you broke up maybe?"

"Yeah," Luke nodded. "Every day."

"So you understand," Jess said. He sat down at the table. "Does it ever get easier?"

Luke snorted. "Being around a Gilmore or being around an ex?"

"Both," Jess smirked.

"Not really, no," Luke shook his head and sat down, too. "Are you thinking about not going?"

"I don't know," he told him. "Maybe."

Luke nodded. "Why did you agree to it then?"

"Temporary insanity?" Jess joked but then turned serious. "Who knows? I think I was curious to where she lives and she told me she'd tell me answers at dinner."

"Do you even want to go?"

Jess was quiet for a few seconds. Did he want to have dinner with Rory? He didn't need to think much further. "Yeah. I do."

"Then you better get ready because she's leaving tomorrow," Luke told him as he stood. "And we wouldn't want her last dinner in Stars Hollow to be a mess."

Jess have him a look as he walked out of the apartment and went back downstairs. He stayed seated for a little while longer and tried to focus on not being nervous. It's been twelve years since the two of them were together, he thought. It shouldn't be this hard.

...

"Who's this?"

Jess walked over to his girlfriend, anxious to see what she was looking at. He peered at what she was holding. "That's my Uncle Luke. You'll meet him when we go visit."

She smiled at him, beaming. The picture in her hand close to forgotten. "You were serious about that? You're taking me to Connecticut?"

"I said I would, didn't I?" He smiled at her, placing a quick kiss on her lips.

She smiled back at him. "Just whenever you mention that town, you don't sound eager to go back."

"I go back," he said, sitting down on his couch. "You know my trips I take down there."

"To see your sister and your uncle, yes," she agreed and sat beside him. "But I wasn't sure you would actually take me."

He shook his head. "Jen -"

"Let me finish," she smiled. "You told me very little about your life there. I was just wondering if maybe you...were, you know, embarrassed to bring me with you."

"That's not it at -"

She cut him off. "It's okay. I'm just glad you're saying it now."

"I'm not embarrassed of you," he told her then let out a small laugh as his next words came out. "I'm embarrassed of them."

"Promise?" She laughed.

He wrapped his arms around her. "Promise."

A little while later, Jen remembered the picture she was looking at before she questioned Jess and went to pick it up. In the pile was a bunch of other pictures beneath it so she picked thoae up, too. She flipped through the pictures until reaching one she hasn't been expecting.

The picture was of Jess and a beautiful brunette. She had sparkling blue eyes and a smile as wide as the moon in the picture. Jess' arms was wrapped around her and he was pulling her closer to him it seemed. But it wasn't any of those things that was getting to her. It was the look on Jess' face.

He had a smile like she'd never seen him make before and his eyes lit up brighter, too.

"The food will be here in fifteen minutes," Jess said as he walked back into the room. He noticed his girlfriend standing there, staring at a photo in her hand. "What's that?"

Jen handed him the picture and his eyes almost bugged out. "Is that her?"

"Where did you find this?" He asked, ignoring her question. Jess stared at the picture too now, his thoughts going back to the day Lorelai took that picture.

"Right here," she pointed to where she found the picture of Jess and Luke earlier. She turned to him now and watched him look at the picture. "Is that her, Jess?"

"Who?" He sighed.

"You know who," she told him. "The girl you told me about when we met. The one that made you not want relationships."

He blew out a breath. "Yeah, that's her."

Jess slumped down on the couch. She followed and sat beside him, waiting for him to talk. When he didn't, she spoke again. "Are you finally going to tell me her name?"

"Doesn't matter," he shook his head. "Me and her...that's long over. What does matter is me and you. You're the one I'm with."

"Jess..." She closed her eyes then opened them again. "How long have I known you?"

"Three years," he answered.

"How long have we been together?"

He looked at her like it was a trick question to say he forgot their anniversary but then finally answered. "One and a half."

"And why did it take us a year and a half to date?"

"Because I was broody and a jackass?"

Jen laughed. "No. Well, yes, but no."

Jess laughed with her. "Fine. Tell me why it took us so long. Since I so clearly understand what you're thinking tonight."

"It's because of her," she answered, all laughter aside. She pointed at the picture still in Jess' hand. "Whatever her name is, she did something to you. Something that made you want to swear all relationships for the rest of your life. I saw you. You hooked up but none of them ever lasted. It was her."

"Rory."

"What?"

"Her name is Rory," he sighed. "And she did do something to me. But to be fair, I did something first."

She nodded. "What did you do?"

He made a face. "I don't really want to talk about that right now."

"Why not?" She asked. "Because its hard?"

"That's part of it," he nodded.

"What's the other part?" Jen questioned.

Jess smirked and nudged at her arm. "Our food should be here very soon."

She smiled and laughed, hiding her face by his shoulder. "I guess it can wait until after we eat."

Just then there was a knock on the door and Jess got up to go answer it. Jen called his name and he turned to look at her as he stood in front of the door.

"You really will tell me?" She asked. "You're not just trying to get out of this conversation?"

"Yes," he nodded. "I really will tell you."

"Okay, good," she smiled as he opened the door and paid for their dinner.

...

"How's this look?" Rory stood in front of her mothers mirror and checked her outfit.

"Hon, wear whatever you want," Lorelai told her. "Its not like it's a date. Its not a date right?"

"No, it's not a date," Rory confirmed. "But its been a really long time since we hung out. I don't want it be weird."

"I hate to tell you this, babe, but..." Lorelai took a breath to extend the moment. "If its going to be awkward, it will be no matter what you wear."

"You're right," Rory collapsed on the bed. "Why am I over-thinking this so much?"

"Because you wouldn't be you if you didn't," she answered for her daughter.

"Right," Rory laughed. "I'll just wear this. Its not like it's a date and there aren't many fancy places to go to in Stars Hollow."

"That's the spirit, kiddo!" Lorelai exclaimed.

A short time later, Rory headed out to the door to her mothers house and walked to the diner. It was packed and she wondered if people had heard about her and Jess' dinner tonight. Rory didn't think that was possible but she noticed Babette and Kirk staring at her in expectation.

She walked to the counter and put her small purse beside her. Luke came out of the back and smiled at her. "He's getting Evan ready to go so he should be down soon."

"Where's Evan going?" She asked.

"Emily arranged for us to go to some dinner in New Haven, one where kids came come so your mom won't have an excuse to get out of it," he told her.

"Mom didn't tell me that," she laughed lightly.

Luke smiled at her and whispered. "I don't think she's too happy about it to tell anyone."

"Well, that's true," she smiled. "Have fun."

"That's probably unlikely," Luke told her and she laughed again. "You, too."

"Thanks," she gave a genuine smile.

Jess walked down the stairs carrying his cousin in his arms. Rory and Luke both looked towards him and he smiled a small one while he placed Evan on a chair. "He's all ready to go, Uncle Luke."

"Thanks, Jess," Luke told him. "Who knows what Emily would do if he showed up improper?"

"She still hasn't let go of his disapproval?" Rory asked, already knowing the answer because she knew her grandmother.

"No, not really," Luke shook his head. "It's gotten less obvious but it's there."

Jess smirked at his uncle then turned to Rory. "You ready to go?"

"Yeah, all set," she nodded and grabbed her purse. They said a quick goodbye to Luke and Evan, Jess even said bye to their audience to show he knew that were paying attention and then they were out the door.

Jess steered her outside to his car with his hand on the small of her back. She turned to him. "Aren't I supposed to pick where we go since I invited you to dinner?"

He shook his head, smirking. "I figured you'd pick somewhere here. We're not staying here."

"Where are we going then?" She asked.

"Just a place right outside town," he answered. "I'd been there before a couple of times."

She nodded. "You really thought this out then."

"Not really," he smirked. "Luke kind of pressured me by telling me its your last night before going back and don't mess up dinner."

"Okay," she smiled then realized something and stopped right in front of his car. "Am I dressed all right? This might not look fancy if we're going somewhere fancy."

He smirked at her. "It's not fancy."

"Okay, good," she breathed.

Jess opened the passenger door for her and Rory climbed in. He stood beside the door still. "And for the record, Ror...you look beautiful."

She blushed and put her head down, suddenly very interested in her hands. He shut her door and walked to the driver's side, getting in. She looked around the car and tried to change the subject. "You were right. Definitely not your high school car."

He laughed and started to drive. Within twenty minutes they reached a restaurant parking lot. It was a simple looking building and the name was just that, a person's name. Jess got out of the car first and then walked around and opened Rory's door. She got out and gave him a smile then they walked inside.

The first part of the evening was asking how the other is, ordering their meals, and avoiding the big things until their dinner had come. Jess looked up at Rory as she was eating her food and smirked. "What?"

"Is now when I get to ask you where you live?" He asked.

She laughed. "I live in New York City, actually."

He nodded, stunned then laughed, too. "How'd you end up in my city?"

"I think you surrendered your city when you stayed in Philadelphia for ten years," she countered.

"Maybe," he said. "But really. I never pictured you a big apple girl."

"Are you still teasing me for that?" She asked, remembering that day thirteen years ago when she visited him in Washington Square Park.

"A little," he shrugged.

"I actually work there now," she answered. "In New York."

"Does that mean -"

"Yeah, it does."

"Shit, Rory, congratulations," he told her. "You work at the New York Times?"

She nodded, a big smile on her face. "Only for the past three years. Before I did this online magazine for this guy named Hugo. Then there was small newspapers around who started taking notice and the Times called me for an interview."

"That's amazing," he told her with a big smile on his face.

"It is," she agreed. "I had interviewed with them before and it didn't happen so I was hesitant. But then it actually happened and I still feel like I'm pinching myself, to be honest."

"I would, too," he laughed. "I'm proud of you, Rory."

"Well, what about you?" She said. "You've written three books, Jess. That is amazing."

"Its nothing," he waved it off and continued eating. "The Times is a much bigger deal than that."

"I disagree," she replied. "I think they're equal."

"I think the fumes of city life are getting to you if you think working at the New York Times is equal to me writing three short novels," he smirked at her.

"Jess," she said. "I always knew you could do it."

"I know," he put his head down then looked back up at her. "You may have said that before."

"Are you writing anything new?" She asked.

He shrugged again. "There is something I'm working on."

She beamed. "I can't wait to read it."

"Don't get too excited," he told her with a smirk. "It may take a while."

"I can be patient," she replied. "But I'll have you know, your books are my favorites."

He snorted and took a swig of his beer. "You don't have to lie. I'll still pay for your dinner."

"You don't have to pay for my dinner," she told him. "And I'm not lying."

"I'm paying," he shook his head. "And I don't believe you."

"Really?" She asked. "Would I lie to you?"

He stared at her for a second, thinking of the lies they'd both told each other in the past. Instead of dredging that up, Jess went for a joking route and answered with a smirk. "Don't you know its true, there's no one else but you?"

Rory laughed. "Only you could sing some cheesy 80's song in the middle of a conversation and make it sound normal."

"You mean Logan never did that?" He asked before he could think. As soon as he noticed what he had said, he started apologizing. "Shit. I'm sorry."

All traces of laughter were gone and she just nodded. "Its fine. You don't have to worry about it."

"No, really," he said. "I'm sorry about...all of it."

Rory nodded. "Thank you."

It was his turn to nod and they finished their dinner soon after. Jess fulfilled his promise of paying the bill despite Rory's objections and pouts. They left the restaurant and instead of walking to his car, Rory stopped and looked across the block.

"What do you say I buy you a drink to make up for dinner?" She asked Jess as he turned to look in the direction she was looking, at a bar people were walking in and out of.

"I say that sounds like a good idea," he told her.

A/N: good or bad? I hope you like! And there will be more on Jen, so be ready to get more into Jess' backstory of the nine years since TRPA too :)