A/N: I wasn't even gonna write this story or even tempt to write a GG fic. But the idea kept eating away at me and I broke down. It's all AU and I'll try to keep Rory and Jess as close to their characters as I can. Certain things will still be the same as on the show but other things are different. I didn't realize just how much I miss Gilmore Girls until I started to read stories on here and start to re-watch the series. Hate it or love it let me know.

Disclaimer: I own nothing related to Gilmore Girls.

Description: Jess grew up with both Liz and Jimmy in Hartford. He got accepted into Chilton with a scholarship only for it to be taken away when he spent too much time with Tristan pulling pranks. His home life slowly crumples around him, leaving Luke to pay for his schooling.

Rory lives with her mother and Luke. Lorelai knows about Luke paying for Jess's schooling but has yet to meet Jess. The only father Rory has ever known is Luke as Chris has never came to visit.

Jess pulled the worn book from his back pocket sliding it across the table. A smirk graced his lips seeing the confusion in the clear blue eyes. "How'd you get my copy of Howl?" Came the small voice. Her blue eyes darting to the book moving back to the brown orbs.

"I found it yesterday." Jess replied seeing the confusion more evident in her eyes. She said nothing knowing it was in her bag all day yesterday. It was right between her folders and Chem. book all day long. That was until the bus ride home when it wasn't there to read.

"It never left my bag Jess." For a reply Jess shrug his shoulders stealing a fry from her tray and getting up. "You took it from my bag didn't you?" She asked annoyed. "Why?"

"Bored." He smirked walking away. Rory huffed stuffing her book in her bag before dealing with her tray. She tried to go after Jess groaning when the warning bells chimed for class. Instead she went to her locker getting the books she needed.

"Oh Mary." Rory refrained from rolling her eyes glancing at the blond boy who casually put his arm around her shoulders. "There's a party this weekend."

"So what Tristan." Rory bit at him trying to break from his grip.

"So?" He questioned pulling Rory into his side once again. "You're my date." He quipped with a smug smirk.

"Say what?" She screeched spinning to look at him. Tristan sent her a wink and walked off stuffing his hands in his pockets. The anger at what Tristan demanded of her was boiling in her veins. There was no way she was going to Tristan's party with him outta everyone.

She slammed her books on her desk her bag falling to the floor with a loud thud. She could feel eyes on her for a few seconds. After class started she felt a pair still on her. She glanced in the direction she knew Jess would be in. For a split second she could she worry in his dark eyes but that was covered up with a smugness smirk tugging on his lips.

"Ms. Gilmore," Was being called breaking the gaze she held with Jess. Rory blushed slightly looking at Max Medina, giving a small smile. "You will be working with Mr. Mariano." The smile Rory held turned into a grin. "Earnest Hemingway is the author you get to dissect for your oral report." The grin on Rory's face slipped into a frown of annoyance. Of all the authors out there she gets stuck with the one she truly despises. She didn't need to look back at Jess to know that he was happy as ever.

~ 1 Year earlier ~

Rory walked through the halls not knowing what to expect. Chilton was completely different than Star Hollows high. Between being called Mary all day long, her locker being stuck and wrecking Paris's project her day had been the worst day of her life. The only plus was when a boy with black hair and deep brown eyes sat at the table across from her at lunch. She glanced up from her Jane Austin novel to get a better look at the boy who sat at her table. He held a small smirk pulling a book of his own out and sat reading. Jess would glance at Rory when he felt her eyes where back on her book.

"Hi." Rory put her book down glancing at the boy before her.

"Hi." He replied his eyes following the words typed on the page he was on.

"I'm Rory." She told him trying to get the boy to say more.

"Jess." Half a smirk spread across his lips. He looked up in time to see Rory stand up. Normally Jess sat by himself to engrossed in his books to par take in a conversation that was based on rumors. But seeing the blue-eyed, brunette a book in front of her not caring about the people around her, he could tell she was different.

For the first two weeks of school Jess would take his time getting to the lunchroom. He would look at the sea of students until he found the one he was looking for. Everyday Rory tried to talk to him. All she would ever get was a grunt or huh.

"Why?" Rory asked finally having enough. Jess placed his unopened book on the table. He raised an eyebrow placing his arms on the table, giving her a questioning look. "Why do you insist on sitting here? You don't talk no matter how many times I try. God it's so annoying. I don't even know why I don't move elsewhere. Or why I let this bother me. But it does." Rory flushed a light shade of pink over her mini rant.

"It is what it is." Jess smirked seeing further frustration cross her face.

"What's that supposed to mean?" Rory huffed finding the tray of food more interesting than the boy who sat across from her.

"You tell me." He replied getting up walking around the time bending down to whisper. "There is no friend as loyal as a book." With that Jess walked off leaving a very confused Rory behind. That didn't answer her question at all. The words swam around in her head all weekend. She finally just gave up. She had a feeling Jess would never tell her. Outta mind, outta sight. She wanted to avoided him at all costs but quickly learned she couldn't do that, there was something about Jess that kept pulling her back in.

"I figured we could go to your place and get started on this report." Rory spoke up joining Jess in the hall way. She figured it would be easier to stay in Hartford for a few hours.

"Can't." Jess replied glancing at Rory. She in return eyed him up with a small glare. How was Jess supposed to explain that his mother was a drunk and his father decided 6 months ago that this life wasn't for him? That his uncle pays for him to be in Chilton. "We can go to yours though." He pointed out.

"Can't do that either. I have to be at my grandparents' house tonight and I was gonna head to the library to get some work done before hand." The dress she was to wear for the dinner hung in her locker.

"How did you get into this school?" Jess asked with a playful smirk on his lips. Rory gasped gently hitting him. "Ror if you were already heading to the library don't you think I could go with you?" He asked seeing the realization hit her.

"I didn't think of that." She said softly looking at the floor. Jess pulled her into his side. Letting the conversation drop. Rory had to wonder why Jess couldn't have been the guy that wanted to go to parties with her. The guy that liked her the same way she liked him. But according to Jess they were only friends. Being friends was nice but she wanted more and every day she saw the girls at school flirt with him it cut her deep.

The one thing Rory didn't know it had hurt him to see her with Dean. It was at that moment he decided it was best to stay friends with Rory. Even after Rory confessed to him that Dean had broken up with her because he had feelings for some Lindsey chick. He hated to see Rory so broken and fragile. He wouldn't be the cause of that ever. It was better if they stayed friends. He pushed his feelings away. No one could hold a candle to Rory Gilmore.