I do not own any part of the GG world

"Are we going to talk about it?"

Rory was looking over the man whose chest she was laying on. As far as the etiquette for one-night stands went, she was sure that the ex-boyfriend that had the most complicated involvement in her life was the worst possible choice. In hindsight. The 'during' was definitely the best experience she could have ever wished for.

Rory traced circles on Jess' skin and he was running his own fingers on her shoulder. He wasn't the lean boy that he used to be, he had literal hair on his chest now that she was navigating. She didn't want to leave this moment. This was the night never happened all those years ago, and yet she was glad that this was the first time between them. Although neither of them knew what it meant.

"Rory, we don't have the greatest history of talking about things like this." Jess stated without evasiveness, just honesty.

"Would you ever want to do it again?" She asked in a small voice, still speaking down at his chest and not to his face.

"It would be weird to enthusiastic right? I should be cool and something like "yeah, sure, whatever" or shrug, right?" Jess voiced the last part is a monosyllabic grunt that would have made his 18 year old self proud.

Rory smiled into him and looked up to see Jess smiling down at her.

"How enthusiastic?"

Jess pulled her back to lay on top of him and Rory gave a squeal and then a giggle.

"Let me express to you a few things, Ms. Gilmore. It might clear your mind." Then Jess went to work on filling Rory with unwavering happiness and she forgot that they ever had such painful history for a few more hours.

"You WHAT?"

"I slept with Jess last night. The first time was an accident but the second time was-" Rory began.

"There were multiple instances?!" Lorelai gasped into her phone with both shock and pride.

"I don't know what any of it means, and we didn't get a chance to talk much this morning because he had to go back to Philadelphia early. I'm not sure what I'm hoping will happen now. I just know it sucked watching him leave this morning."

"I-Well, you did it, you broke Mommy's brain. You slept with Jess, twice. You haven't talked to him about it yet, but you miss him. I didn't even know you two were talking to each other. Though I suppose talking wouldn't have to be involved." Lorelai was pacing her living room opening and closing her mouth like a guppy.

"Mom, do you think I should call him and talk to him about it? I mean we never really see each other anymore, this was sort of a fluke. I'm worried that if I wait too long it will end like it always does for us."

"You're worried? Okay. So, you slept with Jess. More than once, which means that you both felt it was worth repeating. He had to leave this morning to drive to work, but he spent the night with you anyway. You were sad to see him leave and now you are worrying about things ending badly? AND you called me the next morning, which means you are concerned enough to deal with my opinions on the guy. I really really really hate to say this, but kid; I think you still hold a torch for him. It's up to you, if you feel like it was just for nostalgia's sake that you two got carried away, or if this is something you want to pursue." Lorelai was reeling from the information but was trying not to sway Rory away from Jess in case it would cause a rift between them like it did before.

"So, I should call him." Rory was building her confidence and was pacing her bedroom.

"Rip the band-aid. The sooner you figure out what it means, the sooner you can move forward or move on."

"Right. Okay. And Mom?"

"Yeah?"

"If Jess tells Luke, can you, uh, just let me know if he sounds happy about it?"

"Sometimes I wonder what kind of spell he cast over you ten years ago kid. Let me know how your call and how it goes with Jess. Either way, you should come visit soon and we can have a girl's day. Okay?"

"Count on Saturday. I'll fill you in on how it goes. Love you!"

Jess had come to New York to meet an author on Tuesday, he usually made these trips instead of Matt or Chris because he liked to check out his old haunts and read somewhere for a while like old times. Luke had told Jess that Rory had moved here last year but it still felt weird reaching out to her after their last interactions. It was a big city after all; he could be here every day and still never run into her.

Jess ate his words as he was walking through Washington Square Park and saw a familiar face sitting on his old bench reading. She didn't look up and he knew that he had a very small window of time to make his escape. But before his mind had caught up, he was sitting next to her. She still hadn't looked over yet, and knowing Rory, she might not unless given reason to.

"Huh, I though you hated the Beats." Jess gave his signature smirk and watched the cogs in Rory's mind turn for a moment before she dropped her book and then slowly looked over at Jess. He was somehow unchanged and yet completely new.

"Oh my god, Jess!" Rory lit up and hugged him quickly to both of their surprise. They held the hug a little too long for acquaintances, but maybe not long enough for friends.

"You're here, you're in New York! How did you find me? Why did y-, Wow. It's really nice to see you, Jess."

"I didn't mean to find you, I was just visiting my bench; I see you have been keeping it company for me?"

"Oh, yeah I've been borrowing it, it was one of the only places I knew when I moved here, and I can see why you liked it." Rory giggled awkwardly and absorbed the silence that followed for a millisecond before adding, "So, what's up?" Rory was squirming a little under the awkwardness that was giving her butterflies and making her want to puke.

"I'm just here for the day, to meet with an author. Hey, do you have to be anywhere? I have a few hours and I was coming here to read anyway. Coffee?" Jess' words were out before he could filter them and his hand was touching her arm. He expected that the next time he would see Rory Gilmore that he would be angry, or indifferent. He was wrong.

Rory nodded a little too quickly and they left the bench together heading out of the park. Neither of them knew that the next few hours would be a whirlwind of nostalgia and flirting and nervous kissing that led to previously unfulfilled fantasies.

"Hey, you called." Jess said into his phone Thursday night as he was leaving the office. Jess was relieved that Rory had made the first move because he had been trying and failing to call her over the last two days. He just kept thinking 'she won't want you to call' every time he got close.

"That's okay, right? Too weird?" Rory spilled nervous energy. Jess answered before she could anxiously hang up as she had been doing for the last hour.

"Definitely okay. So…"

"Right, so…"

"I'm nervous too Rory, let's regroup."

"Yeah, okay. Regroup. Well, I wanted to talk to you."

"Hence the call, which I'm glad you made."

"Right, uh, so we should have the talk."

"Good talk or bad talk?"

"I guess that depends on how you felt about the other day.."

"It was amazing, Rory."

"Yeah? Then I hope this is the good talk."

"I'd like that."

"Would you want to do it again?" Rory repeated her words from that night.

"I think I made my feelings clear on that particular question. Do you have something in mind?"

"Well, I guess I'm actually asking, well: What are you doing this weekend?" Jess smiled at Rory being so nervous and was surprised at being so calm about it. He did want to see her again. He knew that Rory wanted to know what that meant as the bigger picture, but for right now, Jess was just living in the freshness of being around her again.

"I have a Sunday totally free, how would you feel about heading my way?"

"Well, I'm actually going to Stars Hollow for the weekend; sorry I should have remembered that before I asked you. Um, do you have any days open next week?"

"Why don't I meet you in Stars Hollow? I would love to see the look on Luke's face if I showed up in the diner with you."

"Really? I thought you hated it there. It's okay Jess; we can wait a few more days."

"I don't hate it there, I visit Luke and Doula every once in a while."

"Meet you there then, I'm going Saturday, so let me know when you are headed down and we can meet?"

"I will. And Rory?"

"Yes?"

"I'm glad you called."

"Me too."

Stars Hollow with Rory Gilmore. Well, history tends to repeat itself.

Thanks for reading! Let me know if you want to see a new chapter this week (: