Author's Note: Okay this is a little side project that I just HAD to write because it looked like SO much fun. No worries though, I won't let it distract me from my other projects, I promise.

Chapter 1

"Hun wake up! I don't want to be late and we have to meet with the headmaster today." Diane Davenport said as she knocked on the door to her son's room.

Tristan groaned but sat up all the same with a smile on his face. He looked over at the school uniform that hung on his closet door. His first day at Chilton. Even though he knew he would miss his friends at his old school, Chilton was the only way he would ever reach his dreams of going to Harvard. Lucky for him, he was getting into the prep school on a full scholarship because of his high grades, without it, the tuition would be too much to handle. He only hoped that he wouldn't be too far behind. It was already a month and a half into the school year.

"Tristan, did you pick up the dry cleaning?" his mother called worriedly.

Tristan sighed. His mother would have been lost without him. "In your closet mom!" he called.

"Thanks honey!" she said as she ran past his door in a rush.

"Today is going to be great." he said to himself beaming. He looked over at his clock. "That is if I'm not late!" he exclaimed hurriedly and ran off to get the day started.

Fifteen minutes later he was following his mom to their Jeep.

"Good morning Stars Hollow." he said quietly.

"Tristan, come on, if you wanna get some coffee before school, which I know you do, we have to get going." his mom called as she climbed into the Jeep.

"To Luke's!" he agreed, hurriedly getting into the car.

"So, did you talk to Lane last night?" Diane asked, making small talk as they drove towards the diner.

"Yeah, I'm going to meet her after school today." Tristan said as they pulled into the town square.

"And you're taking the bus home right? I have to work late at the inn tonight." she said as they pulled to a stop in front of the diner.

"Yeah mom."

"Luke!" she called as they walked into the diner.

"Diane and Tristan, what a surprise." Luke said sarcastically as he walked out from the kitchen.

"Coffee?" she asked hopefully.

"No." Luke replied simply.

"Why?" she asked putting on her best puppy face.

"Because, every morning you and your son come in here begging for coffee that will rot your insides and I tell you no. But you persist and refuse to leave until I give you coffee. Then you go and I think that finally you are satisfied but then you come in for dinner and beg for even more coffee. I have to put a stop to it once and for all."

"You forgot all the times we come in here just because. And your little speech about all the junk food we eat." Diane pointed out.

"Mom, are you trying to encourage him?" Tristan asked.

"So, your first day at the Chilton. Nervous?" Luke asked Tristan as he poured them two cups of coffee despite his previous statement.

"Nope, not as long as I have this life giving liquid." Tristan mused as he and his mother both took a swig.

"Luke!" Taylor shouted as he came in complaining.

"What?"

"Did you do that!?" he shouted as he pointed outside to Stars Hollow's first stop light. The big yellow sign had been taken off and put back on upside down with a large red "X" on it.

"Now why would I do that?" Luke said innocently.

"Because you are sorely against this town's modernization!"

"Modernization?! Taylor, we are modernized! I don't see any outhouses! We have electricity!"

"That's beside the point!"

"Are you going to order anything?" Luke asked walking around the counter.

"No!"

"Then get out!" he ordered.

"What?" Taylor asked in shock as Luke grabbed him and led him to the door.

"I'm going to do further investigation of this matter!" Taylor huffed but he left all the same.

"Yeah you do that!" Luke shouted angrily at his retreating back. He turned back and walked behind the counter again. "Jess!" he shouted.

"What?" the boy said coming down the stairs.

"Did you vandalize the crosswalk sign?"

"Maybe, maybe not." he said bravely.

"Well, if you didn't, no punishment. If you did," he turned and looked at him, with he a smirk he added, "no punishment."

Jess gave his devil-don't-care look. "Thanks Luke, later."

With that he headed off to what was hopefully school.

"We have to go too, Luke." Diane said gathering her coat and purse.

"Okay, later Di, have a good first day, Tris."

They waved back and got into the car.

An hour later the mother and son stood in front of Chilton Preparatory School.

"It looks very…er…warm." Diane said encouragingly.

"If by warm you mean the gates of Hell." Tristan said.

"Yeah, you're right it's very…"

"Off with your head." Tristan supplied.

"Yup, I don't remember it being this daunting when I went here. Oh well, let's go meet the executioner, also known as Headmaster Charleston."

"Behave."

"What? You know I could be a lot crazier but I'm not. Be thankful. I used to know this Gilmore woman, totally rebellious and very crazy if you ask me."

"What happened to her?"

"I hear she went to Princeton. It's not like I was really friends with her though so I didn't really look into it."

"Do you regret having me?" Tristan said as they got out of the car and were halfway up the steps.

Diane stopped and turned to her son. "What?"

"Do you regret having me? Do you regret not finishing Chilton because of me?"

"No, never! Why would you say that? Have I ever given you the impression that I thought you were a mistake?"

"No, it's just…if it weren't for me then maybe you would have finished school and we wouldn't be where we are today."

"What, you mean a scholarship case?" Tristan nodded. "This is the only thing that we haven't been able to pay for ourselves. Ever. Honey, we aren't poor. I don't regret anything in my life. I'd rather be making a mediocre living than put you through the hell that goes along with being a child of high society. You understand?" Tristan nodded again. "Good, now let's go show these snobby rich people what you're made of!" Diane finished enthusiastically.

They laughed as they made their way through the maze of hallways, passing by students as they went.

"Hello, I'm Diane Davenport, here to meet Headmaster Charleston about my son Tristan Davenport." Diane said politely to the secretary once they entered the office.

"Just a moment." she replied. She walked through a large wooden door and reappeared seconds later. "He'll see you now."

"Thank you." Diane said and led Tristan through the door.

"Ah, Miss Davenport, it's nice to see you after so long." Charleston said extending her hand towards Diane.

"It's good to be back." she said cordially. "He was headmaster when I went here." she whispered to Tristan quietly.

"And how is Mr. DuGrey?" he asked referring to Tristan's father.

"I honestly haven't heard from Michael in a few years." she said as her smile faded.

When she got pregnant at sixteen by the ever-charming DuGrey, she went against her family's wishes and refused to marry him. Doing this caused her parents to disown her.

"I see. We were so sorry to hear about the deaths of your parents, boating accident was it?"

Her jaw visibly clenched at the mention of her parents. The ones who left her homeless with a child. The ones who wrote her out of their wills entirely.

"Yes, it was."

Sensing it was a delicate subject the headmaster decided to change the subject.

"Ah, and you must be Tristan." he said shaking Tristan's hand.

"Yes sir."

"Ah, well, both of you take a seat." he said. Once they were seated he continued. "So, Tristan, you previously attended Stars Hollow High, is that correct?"

"Yes sir."

"And your record says you left with a 4.0 correct?"

"I believe so sir."

"That's impressive, for Stars Hollow, but here at Chilton the academic bar is raised considerably. You will really need to apply yourself. Our students have been hard at work ever since they first stepped into these halls their freshman year, you are starting at a disadvantage. You will need to be up to speed with not only their knowledge from previous years but from the material that has been covered in the first month and a half that you missed this year. Are you willing to go through all that?" Charleston asked seriously.

"I know it will be difficult but I've worked too hard to get to this point in my academic career to give up. I ready and up for the challenge." Tristan replied.

"Good." the headmaster said standing up. The Davenport's followed the suite. "Welcome to your Junior year at Chilton." he said extending his hand towards Tristan.

Tristan accepted the hand. "Thank you."

"Your welcome, go to the academic office for your schedule, locker assignments, et cetera. Have a good day."

Taking it as a cue to leave Tristan and Diane stood and walked out.

"Okay, Tris, can you take it from here?" Diane asked as they stood outside the hall.

"Yeah mom, I'm a big boy now. I think I can manage." Tristan said jokingly.

"Eh, disrespect me like that one more time mister and no more coffee for you!" she said pointing an accusing finger towards him.

She broke out into a smile and hugged him.

"Okay, Luke's for dinner?" she asked.

"Of course, who else? Al's Pancake World?" he joked.

"Please, don't even joke. Al should have kept to pancakes. Bye, I have to go make sure Sookie doesn't burn down the kitchen."

"Bug Michel for me!" he called at her retreating form.

"Always!" she said back.

* * * * *

By the time Tristan was settled it was already third period, English. He sat down just before the bell rang. The teacher leaned back against his desk to address the class.

"Well class. Today we have a new student. Everyone say hello to Tristan Davenport."

There was a chorus of mumbled greetings. Tristan tensed as two girls, one blond and the other brunette sitting to the right of him looked at him suggestively, in an almost taunting manner.

"Okay, so let's start right away. Can anyone tell me, what Shakespearean play had what is considered to be Shakespeare's goodbye to theatre?"

Two hands went up immediately. Tristan's and a girl with long blond hair sitting in the next row over in the front seat.

"Paris, why don't we let Tristan answer this one."

Paris Geller's mouth dropped open in shock. She turned around and gave him a death glare. Who did this guy think he is?

"The Tempest" Tristan answered.

"Correct, that is what we are going to be starting today…"

He was cut off when a blue-eyed girl with brown hair sauntered into the class with a smirk on her face. Tristan took note of her un-tucked white button down and rolled plaid skirt to make it shorter, showing off her legs.

"Sorry I'm late Mr. Medina." she said casually, snapping her gum at him. She gave him a devilish smile and walked towards her seat next to the two girls who checked out Tristan earlier.

"Nice of you to join us." he said sarcastically. "Please see me after class for you're detention."

Ignoring him she noticed Tristan. Snapping her gum again she asked, "Who's the new guy?"

Max sighed. "Tristan Davenport, meet Rory Hayden."