September 4th

The summer had zipped by in the blink of an eye it seemed. The first summer Jess had been allowed to work what he would consider was more like part-time than what Luke had allowed during school. He had appreciated the extra money that was slowly building in his car fund tucked safely in his sock drawer and honestly, he sort of appreciated that Luke hadn't allowed him to work full-time hours as it had made time for Jess to enjoy his summer as well. Luke always seemed to know the balance that would work best for Jess, even though Jess would never admit that to him.

Saying goodbye on their last day of Stars Hollow High hadn't been too hard for him and Rory. They knew they would still see Lane and Pete regularly and the rest of their classmates weren't much of a concern to either of the teens. The eve before their last day, Rory had been going on and on about missing a few certain teachers, but in Jess' mind, they could all stuff it. If he never had to see Ms. Harper again, it would be too soon. Mrs. Truly was sad to see her two best students go, but even Jess had agreed that the two would keep her updated on their progress and come to her with new book suggestions when they could. When the last bell rang, the siblings were officially Chilton students, and Jess only hoped he wouldn't feel the need to look back.

He couldn't believe how fast the last few months had gone. He had always heard time goes faster the longer you are living and he supposed it made sense. A four-year-old would feel as if a day crawled by as one day in their life was a huge chunk of their entire time on earth. Yet, to a forty-year-old, one day, twenty-four hours, didn't make a huge impact in the grand scheme of things. It was this summer in particular that made Jess start to realize he was getting old enough to not notice the moments ticking away before they were gone altogether.

"Here sweets, I hemmed your skirt for Monday," a frazzled Lorelai handed the plaid piece to the girl as she whirled through the room. "Jess for the fiftieth time I need you to try on your pants. Chilton made themselves very clear that you are to look sharp. I doubt that includes sending you to school with three inches of pant leg dragging on the floor."

"If you know it's three inches, then why do I have to bother trying them on?" He was being difficult he knew, yet the possibility of holding off wearing that awful uniform until the very last minute was too tempting not to try.

"It's either drag or have your ankles show kid. Those are your options if you don't want to put on the dang pants."

Jess sighed dramatically, "I don't want to hear a single word about how I look like a cute little boarding school boy," he warned snatching the garment from her clutches.

"Oh come on, they are cute!" She defended as he shut the door.

"We need to get him a date, he's far too grumpy," Lorelai concluded turning to her daughter. "Speaking of dates, are you still going out with Dean tonight?"

Rory rolled her eyes, "It's not a date, Lane's going to be there. Besides, I'm pretty sure if anything was going to happen between us, it would have by now," her expression changed to glum.

The mother gave her daughter a sad smile, "Don't fret too much over it sweets. You're young, maybe he's scared to make the first move."

"Are you saying I should make the first move?" the girl asked wide-eyed. "Because I'm pretty sure that's not an option."

Lorelai laughed, "I'm pretty sure it is an option if you want it to be. But just give him time Hun. If I've learned anything about relationships it's that they always take lots and lots of time," she rolled her eyes playfully.

The teen sighed with frustration, "Fine. I'm not a patient person you know."

The woman laughed out loud, "Well you are my daughter."

Jess chose that moment to push open his door, "They're like a foot too long!" he grumbled, dragging the long fabric along with him.

"Ah, and why Lorelai are you making me try these pants on again?" Lorelai replied in mocking.

"Yeah, yeah," Jess waved his hand, "Can you just pin them so I can take them off?"

"Somebody's crabby for a Saturday," the woman noted as she got to work.

"The last Saturday before school starts does that to me," he concluded.

"Well, I for one am glad school's starting. You have been bored since the start of August."

"When have I ever complained I was bored?" Jess countered in defence.

"You didn't have to complain. I know you kid. You've been driving me up the wall," Lorelai pointed out, "Your big brain needs to be challenged."

"Yeah and we all know school does that," Jess added sarcastically, rolling his eyes.

"Yes," she nodded, "This school will. I know you have doubts, but I'm confident you're going to be much happier there."

Jess gave a doubtful look as Rory spoke up, "I know I will! Did you see their library Jess!? I might not even make any new friends. I'll just spend all my free time in there," She joked.

"Gee that's healthy," Jess teased, though he imagined himself doing just that. He still wasn't quite convinced the kids at their new school would be any better than the ones at their old. Probably worse considering they were all coming from a background like the elder Gilmores. He would have to take up smoking just to cope, no matter what Luke would say. Okay maybe not.

September 7th

"Alright, just one more picture!"

"Lorelai," Jess sighed as he and Rory stood on the front porch dressed in their newest threads and sporting brand new backpacks sitting neatly on both shoulders. Like a couple of preppy kids, Jess thought absently.

"Yeah Lorelai I think they've had enough," Luke stepped in. They had been taking photos for the last ten minutes after all.

"Oh okay," she relented, resting her camera loosely on her hip, "You know you'll be glad to have these pictures one day."

"Mom, we do appreciate it!" The prodigal daughter assured, "But you'll see us in these uniforms every day for the next three years. There will be plenty more photo opportunities."

"Better not be," Jess mumbled as Lorelai exclaimed, "But not 'first day at Chilton' photo opportunities! Luke, can you believe how big our babies are? The next thing you know we'll be taking photos of them moving into a college dorm!"

Luke nodded once, allowing himself to smile proudly at his kids as well. The truth was, they were growing up fast. He realized it more and more each day. In another few months Jess would be driving and it would only be a blink before they were moving out of the house. These thoughts made Luke start to feel panic creeping up through his body, though, so instead, he ushered them along. "They won't be going to college if they don't make it to their first day of Chilton first, and your bus will be here in less than ten minutes, so get a move on."

"If we miss it we'll just catch the next one."

"Jess."

"I'm kidding."

The bus dropped the kids off right in front of the school and for a moment the pair stood in awe at the grand architecture.

"I don't think I'll ever get used to the size of this place," Rory admitted, staring at the large building.

"Maybe by graduation," Jess hoped, suddenly feeling slightly uneasy as well. "You ready?"

"As I'll ever be," Rory took a deep breath.

They picked up their schedules in the main foyer with the rest of the students. It was slightly less awkward to be the new kids on the first day of the year since everyone was learning a new schedule as well and for that the siblings were grateful.

Jess found their schedules side by side and grabbed them off the table just as a familiar face stormed into his personal space.

"Move," Ordered the irritated voice of a blonde girl Jess recognized from their tour the previous spring. Glaring girl, he recalled.

"Well aren't we bright-eyed and bushy-tailed this morning," he drawled to her sarcastically.

"I'd be a little more 'bushy tailed' if I didn't have all these incompetent new kids fumbling around like chickens with their heads cut off," she snapped back as she grabbed her schedule off the table.

"What's your problem," Rory spoke up with a face.

Her gaze focused on them once more and she began sizing them up with a cold look. "You're my problem," she informed, staring Rory down. "You and your boyfriend thinking you can just waltz in here and upset the whole dynamic of this school."

"He's my brother," Rory corrected with irritation.

"Yeah and right now he's getting on my last nerve."

"He's just standing there."

"Exactly. Listen, I own this school and I don't care how many recommendations from your English teacher you have or how high your test scores are, this is my turf and you'd do well to remember that."

The girl pushed passed Jess, storming down the hall as students tripped to get out of her way.

Jess shook his head, "What a freak."

"She's definitely intense," Rory noted.

"That's Paris Geller," a nervous looking blond informed the pair, "You'd be best to stay clear of her unless you want your life ruined."

"That's a bit dramatic, don't you think?" Jess eyed the jumpy lad.

"If you pose a threat to Paris Geller, she makes you sorry for ever auditioning for that Broadway play, believe me," he informed with horror in his eyes, "She doesn't even like Broadway," he mumbled to himself as he took off down the hallway, books pulled tightly to his chest.

"Did we just walk into 'The Breakfast Club'?" Jess asked shaking his head.

"It's all very peculiar," Rory replied thoughtfully as she watched him go, "What's your first class?"

"English, Mr. Medina."

"Me too," She smiled, glad that they didn't have to part ways just yet.

They found their first class without much difficulty, unfortunately realizing that they shared first period with none other than the Chilton Queen herself.

"How many classes do you think we have with her?" Jess whispered as they searched the room for two empty seats. Jess usually liked to sit in the back of the class whereas Rory preferred the front. Promising not to abandon each other on the first day unless absolutely necessary, they compromised on desks closer to the middle of the room. Rory turning down Jess' plea for seats by the window, if only because she knew it would distract her brother and that was the last thing he needed.

"Hopefully just one, otherwise it's going to be an interesting year," Rory sighed back.

As they settled into their seats, Rory watched as a medium-sized blond boy entered the room and sized her up right away. She heard him whisper to his friend, "Who's that?"

"New kids I guess?" The other boy shrugged and Rory turned away, feeling like an animal at the zoo.

"Just ignore them Tristan, they're of no interest to you," Paris spoke up from two desks over.

Tristan, as they just learned his name, only smirked and moved closer, "I think they're very interesting," he spoke, though only looking at Rory, "Tristan Dugray," he held out his hand, "Looks like we got ourselves a Mary."

"Oh, my name's Rory," she corrected.

"Whatever you say, Mary," he only smiled back and Rory was left without words.

"She said her name's Rory," Jess spoke up for her, clearly agitated by the whole production.

"And who do we have here?" Tristan sized him up, "I think I remember hearing about you. You're the one with the chart-topping test scores aren't you? A personal invitation to Chilton," the blond recalled to whoever was listening. "Well Prep, you must be yearning to get some learning started. I hope we're not all too dumb for you."

"Jeez if I didn't know any better I'd say the zip code of this school was 90210 with the way you all act," Jess shook his head.

"Into girly shows too I see," Tristan smirked.

"Just calling it like I see it," Jess shrugged with ease.

A middle age man chose that moment to enter the classroom and called everyone to attention, "Find your seats quickly please, we have a lot to go over today."

The boys gave each other one last look before Tristan pushed off the desk he was leaning on and found his seat. Jess shook his head to Rory who only shrugged in return as she focused her attention on the man who was now standing at the front of the room.

It was then that Jess first got a look at their new Lit teacher. He was middle-aged, yet that didn't seem to stop nearly every girl in the room from staring with stars in their eyes. Though he knew she hated it when he distracted her in class, he couldn't help but whisper to his sister.

"Please tell me you're not going to go all doe-eyed with this guy too," he gestured to the room of smitten gals.

Rory however, only made a face. "Not factoring in the age difference, he's more of my mom's type than mine anyhow."

"So he's Luke level hot?" Jess made a face and shot another glance at the man.

"I told you, it's too gross to think about."

"I'm sorry I asked," Jess agreed, turning back to the front of the class and realizing he had better start figuring out what the man was talking about if he wanted to try to keep up with this new school.

The class was long and there was definitely no ease in, 'let's get to know each other' period. Jess wasn't put off by this. He actually found the class sort of interesting and had to admit that the guy was more than just a pretty face, he really did seem to know what he was talking about too. He talked easily with the class and let the discussion come naturally, something Jess respected. Jess almost felt the urge to raise his hand and join in at one point, but he didn't. He wasn't quite there yet.

English classes were never all that bad, however, and it didn't ease the way for the rest of the day. By lunchtime, Jess already had an arm full of textbooks from the first half of his classes. Homework was going to drown him by eighth period he was sure of it. He was already exhausted. His fear that the new school would be hard work was an understatement and so far the classes weren't persuading the teen either way. In some ways, he could feel they were more challenging, but mostly they were the same old classes with double the amount of work involved. Already the thought of sitting at his desk all night pouring over his work sounded tiring and drained his spirits.

"Jess!" Rory called, grinning wide when she saw her brother passing by as she exited her classroom.

"How was Psych?" the brother asked once they were side by side.

"Great! You know I could deal with fewer choice students, but these classes are amazing! I already feel like I've learned so much and it's only day one! How was Chem?"

"Not as fascinating as Psych evidently," he smirked.

"Oh come on, admit it, you don't hate this place like you thought you would."

"I'll admit that we're never going to see the light of day again with all this work they're forcing on us. I'm serious Ror, there's got to be some child labour law against it."

The girl only shrugged, "Maybe it's a bit excessive, but it's worth it if it's going to get us into better colleges, right?"

The boy rolled his eyes, not prepared to start yet another argument about whether or not Jess would even be attending a post-secondary school in three years. "You hungry? I'm starved and if we don't hurry we'll miss all the good escargot in the cafeteria."

He turned quickly in the direction of his locker, pulling Rory to follow suit only to slam into a familiar elbow forcefully.

"Oops! Might want to watch where you're going, Prep," Tristan spoke as the shorter boy's books tumbled to the floor.

"You got a problem man? Caus I can make you mine," Jess threatened, slamming into the blond's chest. He had learned how to handle a bully years ago and cocky dicks never troubled him anymore.

"What is going on here?" Jess watched the principal march towards him.

Tristan straightened up immediately, "Sorry Principal Charleston. I accidentally ran into the new kid here and I guess he got the wrong idea about my actions."

Jess opened his mouth to defend himself, but the man beat him to it.

"We do not condone violence of any kind at our school Mr. Mariano. I advise you to adhere to that. This is your one and only warning on the matter."

Jess saw Tristan's smirk from the corner of his eye as he apologized and attempted to look contrite. He would get that asshole back that was for sure.

Once the principal was out of earshot the blond spoke up. "Might want to leave the bad boy act at home Prep. You don't pull it off well."

Jess attempted another move toward him, but Rory pulled him back, "Jess, he's not worth it."

"Listen to your girlfriend, wouldn't want a Prep like you to get detention now would we?"

"He's not my- Ugh never mind! Let's go Jess!"

"See ya Mary"

"It's Rory!"

"How was your day?" Luke asked the teens as they returned home.

"Crap," Jess grumbled, throwing his book bag on the couch and stomping to his room, swinging the door closed behind him.

"Rory?" the man looked expectantly, "Care to fill me in?"

"It could have gone better," she shrugged but smiled a moment later. "The classes were great!"

"Yeah? You sure have quite the armload of books. That all homework?"

"Chilton doesn't mess around," the girl's smile widened. The only kid in history to love schoolwork that much, Luke shook his head.

A silence rested between them as they stared at each other, Rory eager to put her books down and get to work. Finally, Luke spoke his mind, asking the question he knew Rory had the answer to.

"Should I go talk to him," Luke motioned in the direction of the disgruntled teen.

"He'll be okay," she assured, "You know Jess has a hard time with change. He'll be settled in a few days."

Luke nodded. If there was one thing he knew Jess didn't handle well, it was change. It wasn't an obvious character trait and on the outside the boy usually appeared calm, cool and collected in any situation. But, after taking care of his nephew for as long as he had, he was more than in tune with the signs. The nervous habits; blasting too loud music when he wasn't accustomed to a new environment, carrying a book with him to hide behind in uncomfortable situations, acting out when he felt out of control. The uncle understood coming from a background like his nephew's, where every change Jess had to go through as a kid had only made situations worse. He was still trying to teach the boy that change could also be a good thing.

"You're probably right," he agreed with the girl.

Rory nodded, "So anyway," she replied, raising her books, "I better get started on this."

"Sure, of course," he waved his hand, "Don't let me slow you down."

Luke knocked twice on Jess' door and waited until he heard the faintest 'yeah?' Before he let himself enter.

Jess was sitting at his desk, though it didn't seem he was doing anything particular other than staring off into space.

"I figured you couldn't get much work done without your books," Luke explained, placing Jess' abandoned bag from the living room onto his bed. "Sounds like you guys have quite a bit of work to do."

"Understatement," the teen sighed, turning to face the man. "It's going to take all night."

"Well you better get to it then," the uncle concluded with hopefulness.

Jess rolled his eyes and turned his back to the man once more, "I just got home. I need time to chill first."

Luke nodded like he expected the fight, "Which is why I waited a half hour before coming in here."

He knew Chilton wouldn't magically transform his nephew overnight, but a man could hope.

The boy sighed again, "It was a really long day uncle Luke. The kids sucked. The classes were intense. I'll get to it eventually, I promise."

Luke sighed in defeat, "Okay bud. I'm going to trust that you know what you're doing. If you get behind it's you who'll get in trouble from the school, not me."

Jess nodded his understanding, evidently prepared to take the consequences if need be.

"Suppers in an hour and I want you in bed by ten tonight so don't wait too long."

"Ten? I'm 15 you know," The boy scoffed.

"Exactly. A growing boy and it was a long day, which you are going to have to get up and do all over tomorrow. You'll thank me in the morning, trust me."

Jess rolled his eyes at the man's back as he left. He zeroed in on the bag now sitting on his bed full of books that he didn't have an ounce of motivation to open. He let out a long breath. It was going to be a long night.

A/N- This chapter has been ready for a while now, but it's been a rough few weeks for me and I wasn't able to give it that last read through until today. I hope you enjoyed the first Chilton installment! Let me know what you think! I may or may not be working on the first Friday night dinner scene as we speak... Please review if you can!