High School, Boys, And Brothers

Summary: Tyler Gilmore was very protective of his little sister, Rory. For his junior year in High School he went to a boarding school in California, where he met Finn Rothschild, Colin McCrea, and the infamous Logan Huntzberger and they soon became best friends. When Lorelai decides she wants Tyler back in Connecticut for his senior year the others follow. They've all enrolled in Chilton with Rory, so Tyler can live at home with his single mom in Stars Hollow.

AN: This starts off end of the summer and Chilton doesn't require any uniform. I've been reading a lot of these stories lately and I've decided I want to write one so here it goes...

Disclaimer: If I owned Gilmore Girls I would be writing season eight, not a story on Fan Fiction...

CHAPTER 1: NEW BOYS, LIMO'S, MOVIE NIGHTS, AND CHILTON

AIRPORT

Rory was beyond excited. Her brother that she hadn't seen for a year was coming home to go to high school with her. Over that year she had changed very much. She use to wear baggy sweats, sneakers, and sweatshirts and now she wore Abercrombie skirts, flip-flops, and Hollister Cami's. Every guy was after her and that would be the same this year.

She stood there with her 34 year old mom, Lorelai. Lorelai had Tyler when she was sixteen with Christopher Hayden, they got married after he was born but when Lorelai found out that she was pregnant with Rory he left. He would send her 1,000 dollar checks every month without a return address so no one could find him, not that they wanted to. Tyler was perfectly happy being the man of the house.

"FLIGHT 33592 HAS JUST LANDED," the man on the PA said.

The two Gilmore's watched as the few people on first class got off until they saw Tyler. They ran up and hugged him tightly. He dropped his bags and hugged them back. He really didn't care about the people staring, he missed his mom and sis. Rory looked behind him and saw three boys standing there. The first one came off to Rory as a nerd with his sweater vest. The second was at least six feet tall, had messy brown locks, and was wearing hot pink sunglasses. The last one was definitely the most attractive to Rory, He was around 5'10, with medium blond hair, and a flirtatious smirk.

"I thought you only had one sister, Mate," The tall one said in an Australian accent looking at Lorelai.

"Oh! I'm his mom, and you're exotic," She corrected.

"Rory, Mom, this is Colin," He said pointing to the nerd,"Finn," pointing to the Aussie, "And Logan." He finished pointing to the blond, who locked eyes with Rory. "Guys, this is my mom, Lorelai, and my sister, Rory."

"Now Love, You don't look so shy," Finn commented.

"Oh I've changed! You like?" She asked, twirling around, directing the last part to Tyler . He just swallowed hard and forced a smile, trying not to fight with her now.

"Well I'm definitely not complaining!" Finn announced giving her a wink earning him a hard kick from Tyler.

The group walked out and got into the limo that Emily had bought them, for special events. She had also bought them a private jet, their house, and new cars. They didn't use the jet much and only used the limo when necessary like today because they had three extra guests. Since the all boy's parents were out of town they were staying with Tyler for a week.

When they got to the house Tyler gave them the grand tour and they each picked their rooms. Logan got the room with the balcony but small closet that was across from Rory's room and below Finn's. Colin got the room across from Tyler's and below the master bedroom. Since they were having a movie night Rory, Logan, Tyler, Finn, and Colin went to Doose's to get food while Lorelai went to pick up the movie.

The teenagers follwed Rory through the aisles each holding a basket that she was quickly filling with candy and poptarts. They quickly paid and met Lorelai at the house. When they were setting up the food Lorelai found out she had to go deal with something at the inn leaving just Rory and the boys. During the middle of the movie Rory fell asleep on Logan and within ten minutes everyone else was out.

MORNING

The next morning everyone went to their respectable rooms to get ready for their first day back at school. Rory decided on wearing a pair of Kino's, white Bermuda shorts, and a tank top that said 'Little Miss Giggles' with smiley faces all over it. She made sure that her hair and make-up were perfect for a certain blond boy. When she came downstairs she received a glare from Tyler.

"Ty, Deal with it I have changed!" She said firmly as she grabbed her coffee.

They soon all got into there cars. Tyler took Colin and Finn in his car since it was a three seat-er and Rory took Logan in her two seat Lamborghini.

RORY'S CAR

"So Rory, What do you like to do?" Logan asked trying to strike up a conversation.

"I like to read, I'm on the paper. You?" She asked taking a quick glance at him.

"Yeah I'm on the paper too, Daddy's orders, Ace," He said smirking at her.

"Ace?" She asked turning into the Chilton parking lot.

"Ace Reporter," He said making her blush.

"Well here we are, good old Chilton!" Rory said as she stepped out of the car followed shortly by Logan.

TYLER'S CAR

"Hey Gilmore, Why do you care so much about how your sister dresses?" Colin asked from the passenger seat of Tyler's Porsche.

"Because she's my little sister and I don't want any one looking below her face or above her knees," Tyler said seriously. "Well here we are. It's weird being back he said as he walked in with his friends.

CHILTON HEADMASTER'S OFFICE

"Hello Headmaster Charlston," Rory said as she entered his office with the boys.

"Rory Gilmore, it's so nice to see you again. Is that you Tyler? So good to see you again too!" He said shaking Tyler's hand. "And who might you three be?" He asked looking at Finn, Colin, and Logan.

"I'm Logan Huntzberger, this is Finnegan, Finn, Rothschild, and Colin McCrea. We're new," Logan explained using the last names on purpose.

"Well it's very nice to meet you!" He said shaking his hand. "Now Rory would you mind helping these boys out today?"

"Of coarse not," She said as they left to go get their matching schedules.