This is my first attempt at fic writing. The characters are owned by ASP and the idea of this story in based off a book by Karen Anders. I wanted to give a BIG Thank You to Season 4.5 for all the help.

AN: Tristan and Rory never went to school together. Lane and Rory are best friends. Tristan and Jess are best friends. Rory and Jess don't know each other. The story is full of bad advice, good intentions and romance. I hope decide to give it a chance.

Rory Hayden sat outside her father's office waiting for his meeting to end. She was supposed to see him so they could discuss plans for her mother's surprise birthday party. While waiting, she began reading through the latest copy of FASHIONISTA, a hip new magazine. Flipping through it, she came to a quiz entitled" Who's Your Hottie?" Skimming over the article, she got to thinking of her non-existent social life. She had her share of fix-ups and stale men her father approved of, but she wanted more. She wanted the spark and passion her parents had. Deciding something drastic was in order she decided to take the quiz and find out who her ideal hottie was, then she would seek him out. She was young, free and ready to have fun.

Tearing the quiz out of the magazine she quickly marked her answers. After tallying her score, a 22, she read the description of her ideal hottie.

If you scored 21-29, -

You crave the BAD BOY. He follows his own rules. Takes

what he wants when he wants it. He will push you to the

limits inside and outside the bedroom. He has a devil-may-care attitude and charm to spare.

The Bad Boy…hmmm. I've never dated anyone who could remotely be considered BAD. Where would…

The sound of the office door opening interrupted her thoughts.

"Ror, I'm so sorry, but the clients want to take me to lunch. Can we reschedule?" her father, Christopher Hayden, asked as he walked toward her.

Checking her watch and tamping down her irritation at the wasted 30 minutes of waiting, she looked at him and smiled her perfect daughter smile and said, "Sure Dad. Give me a call tonight thought. We really need to get started planning."

Kissing him on the cheek she smiled. "I'm going to go back to work. Maybe I'll grab a sandwich on the way back to the Times."

"Thanks hon. I'll call you tonight, I promise."

Watching her father hurry back into his meeting, she decided that was the final straw. She

loved her father, but sometimes he couldn't see beyond his own needs and timetable. She needed to do something for herself. The Bad Boy was the key to it all. Gathering her belongings, as she got ready to leave, she stuffed the quiz into her purse. As an after-thought she decided to stop by her best-friend, Lane's desk.

Her father had hired Lane as a personal assistant for one of his new employees. After quickly filling Lane in on her plans for the evening and promising to call, Rory finally got ready to leave the office. Hearing her father's voice from down the hall, she looked back bypassing his companions and settled her gaze on him. With a quick smile and wave to him she turned back to Lane.

"Okay, so I'll call you later. Maybe we can grab some dinner or something. There are some ideas I want to talk to you about later."

"Sure, I'm here until 4 o'clock, so just give me a ring."

"Bye."

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Tristan Michael DuGrey Jr. was newly hired at Hayden Financial, but he was eager to make his mark. He had just been in Mr. Hayden's office with some clients. As they filed out he looked down the hall and saw a petite brunette talking to his PA, Lane Kim. The brunette turned and he felt like he had been sucker-punched. As the most captivating pair of blue eyes looked right past him and settled their gaze on his boss, he felt a wave of disappointment.

Watching as she departed the office, he noticed a piece of paper on the floor near where she had been standing. After giving his good-byes to the clients and his boss he walked over to Lanes desk, but not before grabbing the paper.

"Hey Lane, who was that?"

Smiling at her boss, "Hi, Mr. DuGrey. You have a couple of messages. Who was who?"

"The small brunette that was just talking to you. Who was she?"

Staring at her boss, she realized who he was talking about and what he was really asking. Narrowing her eyes, she told him, " She is the boss's daughter, Rory Hayden. And you can just forget about whatever you are thinking. It will never happen."

"Why do you say that? Is she dating someone? How do you know her so well?"

"We grew up together. She is my best friend. And I know she doesn't date guys like you, willingly. And she never dates men that work for her father."

"Does she feel like we aren't good enough, because we work for her father? You make her sound very shallow."

"No! Certainly not. Rory would never think that about anyone. She is the nicest person I know. She just doesn't date stockbrokers. She thinks they are boring. So, unless her father set her up, she tries to stay away from that "type".

"Lane, do you think I'm boring? Am I your typical stockbroker?"

"You Mr. DuGrey? Not a chance. I think you broke the mold. But either way you look at

it, it just won't work."

"Thanks for the advice Lane."

Turning to go back to his office, Tristan looked down and remembered the paper in his hand. Opening it up he realized it was a quiz out of a magazine. Remembering that Rory had the magazine FASHIONISTA in her hand, he realized she must have taken the quiz.

Once settled behind his desk he took another look at the paper. He had struck gold, because he had a drawn-up blueprint to Rory's ideal man. Now how to go about using this information to make her see his would require some thinking. After looking over her responses and tallying her score he checked the descriptions of men and found the one

correlating to her score. He bypassed, PROFESSIONAL. Surprise, surprise, ALL-AMERICAN BOY, INTELLECTUAL, ARTIST and came to the final one. The one Rory wanted – BAD BOY.

Sighing, he leaned back in his leather office chair. Rory wants a Bad Boy. The one guy he didn't understand. He could be any one of the other types, but Bad Boy…that was so far from his personality. He shouldn't really be surprised that she wanted someone so unlike a stockbroker. This was going to require some major help from his best friend and old college roommate, the original bad boy, Jess Mariano.

Please review. Let me know what you thought, if you had any suggestions, etc.