A/N: Thanks to the revival and news of Milo returning, I was struck with inspiration. Please note that this takes place after Jess's last episode, but it's what happened if she would've gone through in sleeping with him and cheating on Logan instead of walking out. Let's forget that the most heartbreaking line in history ("It's what it is. You, me.") never happened.

Also, I'll be updating my other Lit fics tonight, but inspiration hit and I had to get it out. I hope you guys enjoy! Please favorite, follow, and review if you like. It really keeps me going when I know that people like my work!

"Because he had no place he could stay without getting tired of it because there was nowhere to go but everywhere, keep rolling under the stars…"

-On The Road by Jack Kerouac

As Jess pulled up to Stars Hollow, he got out of his car and sat on the hood. The Ramones played loudly in the background, but it still didn't bother him. In a sense, the sheer aggression and deafening noise seemed to comfort him. Especially right now, when he was about to step foot back in the town that he swore he hated. He made sparse visits to the place he once called home. Of course, the majority of the time that he spent there was hell, but it had a few ups, like Rory, for example. Sadly, it had been almost ten years since the two were in the same room together. After that night, she sadly went back to Logan. Jess always thought it was a terrible choice, but he heard through the grapevine that they had broken up eventually. He would've asked it about her himself, but every time he was in town, she mysteriously vanished; she had a great career that came with a lot of travelling, but Jess thought for sure that she'd have to show up sooner or later. Maybe this time she was around, he hoped. Every time he had that thought, though, she wouldn't be home.

He shrugged to himself and pulled himself back into reality. "Sheena is a Punk Rocker" played on loudly in the background, making Jess crack a smile. In that instance, he almost wanted Taylor to pull up next to him, just so that he could get the joy of annoying the man once more. At this point, he would even let Taylor call him a hoodlum for the millionth time, but just for old times sake. Instead of letting the anxieties and thoughts of what could happen eat him up, he got back into his car and pulled into town. The "Welcome to Stars Hollow" sign was only what felt like a two second drive away from Luke's, but something about the road made it feel like it had stretched on forever. As he pulled to the side of the road, he took one look around and suddenly realized that the place hadn't changed one bit. It was perfectly preserved in a globe by scientists, he thought. That could've been the only explanation of it not changing one bit since he was sixteen. Getting out of his car oddly resembled the first time he stepped off of the bus and met up with Luke after his mom pawned him off on his uncle. He tried not to think of old memories, but this was the one place in the whole world that made nostalgia creep up on him. Jess had lived in multiple places across the country, but every time he walked into this town, he realized that it was the only place that truly felt like home. Maybe it was because it felt like stepping into some weird Leave It To Beaver world, but whatever it was, it definitely had a grasp on him to this very day.

He swung the door open and heard the bell above ring. Something about it was oddly comforting. Looking around, he could tell that he had gotten there just in time for the lunchtime rush. Instead of darting off to find his uncle, he stepped behind the counter and took his old place was a waiter. Jess regretted it immediately when he noticed that Kirk had strolled up and sat across from him at the counter. "What do you want, Kirk?" He let out a frustrated sigh. Jess had no idea why he thought lending a helping hand would be an easy job – it was almost a karmic thing that brought Kirk to sit in front of him.

Upon hearing a different voice, Kirk looked up and glared. "You're not Luke," he said with a confused tone.

"Huh, I was under the impression that I was," Jess stated sarcastically. "What do you want Kirk?"

The older, less mature man huffed. "Pancakes and bacon."

"It's lunch," Jess stated matter-of-factly.

"Luke let's me have pancakes for lunch."

The younger man rubbed the back of his neck and blew out a puff of air. "I'm not Luke. I thought we already established that."

"You're as mean as Luke," he pouted.

Jess was about to give up and walk out, but instead he groaned. "How about a hamburger?"

"That's fine."

"Good, glad we could make a deal." Jess turned around and leaned into the kitchen to let Caesar know. At first Caesar wasn't phased, but a pleased look came to his face as soon as he realized who was speaking. Jess nodded towards him and turned on his heal, but ran straight into his uncle. "Uncle Luke," he greeted him with a large smile and a hug.

"What are you doing here?" Luke seemed more dumbfounded than excited, but he hugged his nephew back before taking a step back and crossing his arms. "And what are you doing behind the counter?"

"Being rude," Kirk answered with a shrug.

Jess rolled his eyes. "Being helpful," he corrected Kirk.

"He's being rude," Kirk told Luke.

Luke closed his eyes and shook his head at Kirk, trying not to acknowledge his presence. If anything, Luke was grateful that his nephew was able to deal with him for at least once that day.

"The customer's always right," Kirk added. Instantly, Jess and Luke shot him a daring glare and the man threw his hands in the air. He was about to speak again, but there was something too threatening about the two that he couldn't bear to do much other than sigh and look down at the counter.

"Where were we?" Luke added as he headed out to hand off coffee, letting Jess follow him. "Oh yeah, so why are you here?"

Jess' eyes widened as he looked at him. "Can a guy just visit his uncle without being bombarded?"

"Geez," Luke groaned, "I won't be asking again."

"Thank you." Instead of continuing any sort of conversation, Jess turned around and headed towards the upstairs office to unpack a few things from his bag. After spending a few moments in peace, he finally brought himself to going back down towards the chaos, but not before grabbing Howl and shoving it in his coat pocket. He planned on heading towards the lake and reading it for old times sake. As he headed down the stairs, he heard the voice of a small girl, asking Luke for waffles. As soon as she asked, Kirk joined in by saying that it wasn't fair. Jess prepared himself for whatever storm he was about to step into with the crazy townsfolk that were as entertaining as they were annoying. "Someone gave you another kid?" Jess joked as he pulled up next to Luke. Luke turned around to see him, forgetting that he was there. In that moment, Luke started to panic. Jess could see it in his eyes, but he wasn't sure the reason behind it.

"Who's that?" the little girl asked as she pointed towards Jess. If he were being honest, he would say that she resembled the Gilmore girls far too much, but he wasn't going to make any conclusions right off the bat.

"My nephew," Luke told her, suddenly sounding annoyed.

He was about to introduce himself, but as soon as he knew it, Lorelai darted through the door and rushed over towards the girl. In that moment he felt that he was right. She was definitely a Gilmore girl. The eyes and hair were what set him off to it – that and the fact that she had their patented quirk to her. He could see it without her even speaking a word. "Jess!" Lorelai hopped in her spot when she saw him standing next to who he presumed to be Rory's little sister. "Where did you come from, kid?"

"Why's everyone interrogating me?" He asked. He sounded more serious than he was, but Lorelai left it alone.

"Well, it's nice to see you," she smiled as her eyes shifted to the girl. " Elinor, we've gotta get going, sweetie."

"Why?" She prompted, looking at the elder Gilmore.

"Because I said so and whatever I say goes."

"Why?" She asked once more, making Lorelai roll her eyes.

"Because I'm the leader of the clan. The provider of the household, the alpha-male, and the one who's in hurry so there's absolutely no chance of arguing with me."

Jess smiled, knowing that he had heard that one before. It wasn't like Lorelai to reuse her lines, but he had to admit that it was a pretty good one.

"When will mom be back?" Elinor asked Lorelai with a frown.

Jess stepped back, preventing Luke from walking towards a customer. "Mom?" he mouthed. Luke shook his head and tried to get out of the situation before it went any further.

"Tonight, remember?" Lorelai stuck her hand out, waiting for her granddaughter to comply. "You sticking around for awhile?" she asked Jess as Elinor put her coat on.

"Uh," Jess stammered, "yeah, I guess so."

"I'll see you later then," she smiled before heading over and giving Luke a peck on the cheek. "You too, mister." Luke swatted her away, acting embarrassed of her gesture, but everyone in town knew that he secretly loved it.

As soon as the girls left, Jess scrunched up his face at his uncle. "Mom?" He asked once more, this time loud enough for the entire diner to hear. "Did Lorelai kidnap someone's kid?"

Luke's jaw dropped, as if he was going to say something, but instead he pursed his lips back together and continued on with his work. It wasn't three seconds later when Jess heard a psst sound coming from down the counter. "What, Kirk?" he snapped.

"Mom is referring to Rory," he told the boy, "now if you'll excuse me. I'd rather talk to people who aren't rude."

Jess' eyes grew wide once more, "No, no, no, no, no," he whispered to himself. He walked out of the diner without saying a word and headed straight for the lake. He had no idea that Rory even had a boyfriend, let alone a kid. She didn't seem like the kid type to him, actually – at least not until her career simmered down. Instead of dwelling, Jess took out his book and read away. He'd apparently see her later that night