Rory pulled her car into a parking spot in front of the school. As she got out of the car, she looked up at the vast carvings on the outside of the building, remembering when she had gone to the school and it had seemed so immense. Heaving a sigh, Rory stepped away from her car and walked into the building. Students milled around in the hallways and a few of them gave Rory looks as she passed by for she wasn't in a uniform. Somehow, Rory's feet still knew where to take her and before she knew it she was standing outside the headmaster's office. But before she could knock the door swung open.

"Ah, Miss Gilmore, it's good to see you again."

"Hello Headmaster." Rory extended her hand to the portly man who took it and shook it.

"Follow me please." Rory nodded and followed the man out of the office and down the hallway. "So how is Yale treating you?" Headmaster tried to make small talk.

"Very well thank you for asking." The headmaster nodded.

"Here we are." He opened the door for her and she walked in. "Miss Gilmore, this is Mrs. Quin, she teaches the class you will be speaking to. Mrs. Quin, this is Miss Gilmore, she will be speaking today."

"Pleased to meet you." Rory smiled at Mrs. Quin.

"Our other speaker just went to the bathroom, he should be back any moment," Mrs. Quin explained.

"I believe you went to school with our other speaker. He's here to speak about an, ah…" Headmaster Charleston seemed to be searching for a word. "Alternative track. Well, I'll leave you to it then. It was good seeing you again Miss Gilmore." The headmaster gave a wave before exiting the room.

"Excuse me, Mrs. Quin," Rory turned to the woman beside her. Her curiosity had been sparked by the headmaster's comment about an 'alternative track'. "Do you know who the other speaker is?" Mrs. Quin opened her mouth to reply, but was cut off as Rory got her answer.

"Mary!" a familiar voice spoke behind Rory. Immediately, Rory turned.

"Tristin!" Rory was shocked to see her former classmate standing in the doorway. For a moment Rory panned his body, taking in his outfit a simple pair of jeans and a tee shirt with a blazer over it. Rory felt awkward for a moment as she realized she was over dressed. It also didn't help that her business attire further proved that she was in fact a 'Mary'. Rory smiled at Tristin as he walked towards her.

"I never thought I'd see you again. How you been?" Rory tried to respond but stopped when Tristin wrapped his arms around her in a hug.

"Oh," Rory was taken aback. She and Tristin had had a past together, but they were never really friends. He had a little crush on her, but she had stifled it when she chose Dean. Rory put her arms around Tristin to reciprocate the hug before pulling back. "I've been great! You?" Rory looked at his face, and saw that military school had been good to him. A face that had once been a cute boy next door face was now a heart pounding gorgeous face. Rory wished once again that she had worn an outfit that showed a bit more skin.

"A great as I could be going to military school."

"Well you should be out of that by now."

"Yeah I'm actually…"

"Ok class, sit down." Mrs. Quin clapped her hands and Rory and Tristin turned to her. Sharply, Mrs. Quin turned to the two of them with a pointed look. As they tried to suppress their giggles, the two of them found seats.

"Well that was…interesting." Rory commented as she and Tristin walked out of the building towards their cars.

"Were we ever that awkward? I swear half of those boys looked like they were going to pass out when you looked at them."

"You had them swooning yourself mister. 'Um…I was wondering where you got that jacket because it's so hot'." Rory imitated one girl. Tristin laughed. They had arrived at Rory's car and she began to fiddle with her keys. "Well, it was good seeing you again."

"You know, we never really got to talk. Do you want to maybe grab a cup of coffee?" Rory looked up at him. Her mother would be furious, they did have plans. Well actually the Gilmore Girls didn't plan, but they did have an agreement to meet up and do something. Rory looked into Tristin's eyes and immediately found her answer.

"Absolutely."

"Great, tell you what how about you follow me in your car." Rory nodded and then got into her car. As Tristin walked to his car, Rory pulled down her mirror and added a fresh coat of lip gloss.

"I can't believe that with my coffee addiction, I never knew this place was here," Rory said in awe as the two of them walked into the coffee shop.

"I can't believe that you're addicted to coffee."

"Why can't you believe that?" The two had gotten in line and Rory was looking up at the menu.

"It's just not very Mary like of you." Rory turned and Tristin flashed her a dazzling smile.

"Okay you need to cool it with the nickname. I'll have you know that I've done a lot of non Mary like things in my life."

"Do tell."

"Well…" But they had gotten up to the counter.

"I'll have a double, black," Tristin ordered. "And you non Mary?"

"Oh you don't have…"

"Yes I do, what do you want?"

"Vanilla cappuccino, extra foam." Tristin handed the man behind the counter the money for the coffee and then they went to pick their cups up. "That was very nice of you."

"I'm a nice guy. Thanks man." Tristin nodded to the man who handed them their coffees. "I may not have been back in high school, but I changed."

"So I noticed." Rory smiled as she took a sip of her coffee. Tristin pulled out her chair for her and Rory couldn't control it any longer, she laughed out loud. Tristin smiled as he pushed in her chair and then went to sit on his side of the table.

"So tell me about your non Mary escapades." Tristin leaned back in his seat.

"Well I guess it all started with Jess. He was the bad boy that my mom didn't really want me to date. He's also the reason I missed my mom's graduation. Then I went on to sleep with my ex boyfriend, Dean."

"Ah yes, the infamous Dean. Is he still just as freakishly tall?"

Rory nodded. "Well he was my ex at the time and also happened to be married." Tristin choked on his coffee.

"You slept with a married man?" Tristin seemed genuinely surprised.

"Yup."

"I guess I'm not the only one that's changed since high school."

"Oh that's actually not the worst of it. Then my next serious boyfriend and I stole a boat, got arrested, I had to do community service. I dropped out of Yale and moved out of my mom's house. It was bad."

"I'm impressed." Rory smiled and took a victory sip of her coffee.

"So what did you do after you left Chilton?"

"Nothing near as exciting as that. Let's see I got sent to military school, which I think broke my spirit. Adults could actually stand to be in the same room as me for extended periods of time after military school. And then I went on to Harvard. I graduated early, this year actually. Partly because I was tired of school and partially because there was really no need to go back another year." He sipped is coffee.

"I'm sorry, no need? I dropped out of college, remember and I went back because I realized there was a need."

"Ah but you see your daddy isn't loaded."

"So?"

"So he didn't buy you an office building so that you could open your very own law firm."

"You own a law firm?!" Rory was shocked. This was certainly not the Tristin she had gone to school with.

"Not only do I own it, but I run it as well. Which is especially good because that means I can choose the company dress code. They have to wear proper business attire when meeting with clients but other than that, I'm thinking of requiring the girls to wear skirts no longer than midthigh." As Rory rolled her eyes she realized that some things never change.

"You were impressed with me and you've done all of that? I suddenly feel so, under accomplished."

"No you see Rory, I'm impressed with you because you actually live." Tristin set his coffee on the table. "Every day I go into the office and do paperwork or make business calls. I have a routine that's rarely broken. I can't remember the last time I had a date. Or the last time I got totally trashed."

"Last night," Rory said indicating herself.

"See what I mean? You're doing things that normal people our age do. I wish I had that, but you know there's no going back now." Unsure of if she should pity Tristin or smack him for taking his charmed life for granted, Rory avoided eye contact. "Hey, I didn't want to bum you out." Tristin reached his hand out to her.

"No I'm not bummed just a bit confused. How about we change the topic."

"So how's your love life nowadays?"

"Just broke up with my serious boyfriend."

"Why?"

Rory was a bit peeved that he felt he should be privy to her private life, but then she figured that if his love life was really as pitiful as he said the least she could do is let him live vicariously through her.

"We just grew apart is all." Tristin nodded his approval and then Rory's phone rang. "It's my mom," Rory informed him as she pulled the phone from her bag and looked at the caller id. "Sorry." She flipped open her phone. "Hey mom." Her mother's voice angrily yelled back.

"Hey mom? That's all I get? We agreed to do something after your Chilton thing. Are they really keeping you up there that long? How many questions do these damn kids have? Or are they holding you hostage? Should I call the cops?"

"Mom, I'm fine. I just ran into…" But Rory wasn't really sure if she should tell her mom about Tristin, they hadn't gotten along well the first time he was around. "I just ran into someone and so now we're out to coffee. So I'm going to go, don't want to be rude. Love you mom." Rory slammed her phone closed and immediately it began to ring. With the push of a button, Rory's ringer was silenced.

"You and your mom had plans?" Tristin surmised.

"Yeah, but…"

"No buts, I know how important you guys are to each other. And I'm sure she's a lot more fun than I am. Get out of here." Tristin reached into his pocket as Rory talked to him guiltily.

"Are you sure because it's ok I can see her any time." Tristin pulled out a pen and grabbed a napkin from the table.

"And we can see each other any time as well. Here." Confused, Rory looked down at the napkin he had handed to her. In his big sloppy handwriting he had written is number down. She smiled and slipped the napkin into her purse.

"It was good seeing you again Tristin." Awkwardly, she bent down and gave him a hug.

"Bye Miss Hilton." Rory pulled back and gave him a look. "Well Mary doesn't fit anymore but I think Paris Hilton does." Rory grimaced.

"How about you call me by my own name for once?"

"That's not as much fun." Tristin gave a grin and then Rory walked away from him. She wasn't out the door though before he called to her. "Bye Rory!" She smiled before turning around and giving him a wave. Then she drove home to meet her mother.