Disclaimer: I don't own Gilmore Girls. I just have a very fertile imagination. This is my take on what could have happened if Rory realized, before Tristan left, that she wanted him to kiss her goodbye. Enjoy.

A special thanks for TheMavster, for being my new Beta! :)

That went well. Rory thought sarcastically. She had came home, after the play, to find Dean sitting down at her porch. Of course he was mad at her. She had left him standing in the middle of that hall, doing God know what with Richie Rich inside that empty classroom, according to him. The worst part was he wasn't even wrong

"Do you even love me, Rory? Or is it just a joke to you?" He asked her. She had no answer for him. She thought she did, at the beginning. But ever since they were back together, something was missing. When she tried to pinpoint that feeling, to figure out what was missing in their relationship, all she could see was messy blond hair, devilish blue eyes and that smirk that was permanently attached to his face...

So they broke up, again. At least this time she saw it coming. She sighed, sitting on her bed. She couldn't even bring herself to feel sad about it, she was too busy being brokenhearted that Tristan had left. She remembered then that he had given her something, and at that time she was too dazed to pay attention to what it was. She looked for that piece of paper in the middle of her books, where she had shoved it when she got inside the car, and retrieved it. It was an address, Tristan's address, in North Carolina.

She quickly wrote it down on her phonebook, so she wouldn't lose it, and thought about what the hell was she supposed to do with that damn address. Did he expect her to write to him? What would she say? That she was willing to wait for him? And, more importantly, should she be willing to wait for him? She had no idea. She closed her eyes, and was assaulted with the memories of that kiss. She still couldn't believe that she had kissed him. Did she really love him?

"Hey, hun. Are you okay?" Lorelai asked her, entering her bedroom. She was looking at her, concerned. Her daughter was unusually quiet on the way back from Chilton, after the play. She knew something had happened, when Dean walked away from Chilton without a word. Rory looked close to tears now, after seeing him walking out on her, again, after Rory failed to tell him that she loved him, again. She was starting to think that maybe she never really did.

"I'm okay mom. I guess some things just don't work out. I think getting back together was a mistake..." She told her mom. Lorelai sighed, and sat beside her only daughter, trying to comfort her. She already knew that Rory and Dean getting back together was a mistake. That was not what she was worried about right now.

"So, want to tell mommy what happened with Bible Boy in that classroom?"

"Uh. We kissed." Rory told her mom, a little bit uncomfortable. She was afraid of what her mother would think. They had a really open relationship, were best friends, even, except when it came to boys. Then it would get way too awkward.

"Wow. So, what happens now? Are you together?" Lorelai asked, expecting the worst. She didn't want Rory mixed up with those kids, she didn't think they were good enough for her. She didn't want her daughter to go through the inevitable ache of getting her heart broken, and those boys were expert in doing just that.

"Not really. His parents are sending him to Military School, in North Carolina. He left today, before the play." She told her mom. She was getting tear-eyed just thinking about it. She wasn't supposed to feel like this. She wasn't supposed to fall for him.

"Oh. So it was a good-bye kiss?" She asked, trying to understand what was going inside her daughter's head. She looked dejected. Wasn't this the same guy that always got on her nerves, calling her Mary? The main reason that Paris and her crew would pick on her and make her life hell in that school?

"I don't know. He just... kissed me. He kissed me, and then gave me his address in North Carolina, and left." She said quietly. "I can't believe he left just like that. I really don't know what to do. Should I write to him?"

"You'll figure it out, hun." Lorelai said, kissing her daughter's forehead and leaving her alone for a while. She thought it would be best if she didn't interfere, especially when both of them knew what she really thought about those trust fund babies.

Next day at Chilton, the school was abuzz with gossip. Everybody was talking about the King of Chilton being banned from Hartford. Some people were talking about him going to prison, some people were talking about boarding schools, and very few people were talking about how he was sent to Military School. The only good thing about Tristan being gone was that Paris and Rory managed to develop some kind of friendship.

With Dean out of the picture and Tristan gone, Rory was feeling alone, at least in the heart department. Sure, she focused much more on school and on getting into Harvard, but everybody could see that a spark was missing. Some people in Stars Hollow believed that she was upset about Dean, but only a couple of them knew who she was really missing, and Jess Mariano was one of them.

After she and Dean broke up, Jess asked her out on a date, at the "Bid-A-Basket" festival. They went out a couple of times, but Jess could tell that her heart was already taken, and after that, when Luke finally got around to asking Lorelai out, it was too weird. It was almost like dating your cousin. So they decided to be friends.

It was because of Jess' insistence that she decided to write to Tristan. She wrote that first letter almost two months after he was gone, and Tristan wasted no time at all writing back. They never talked about their feelings, or about that kiss they shared right before he was sent away, but they talked about everything else. He was the first person to hear about her decision to attend Yale instead of Harvard, and she was pleased to hear that he, on the other hand, was going to University of Maryland, in Washington, much to his parents despair. But, as he said, it had the best Department of Criminology and Criminal Justice in the US, and she encouraged him to go and follow his dreams.

It started with those letters, and soon they were talking on the phone, at least once a week, sometimes even more. Aside from Jess, and Lane, Tristan was now one of Rory's closest friend. Sure, she was still totally in love with him, and he was still totally in love with her, but both of them were masters in the art of hiding their feelings for one another. Everyone else could figure that out, except the two of them.

They even met a couple of times, during those two years. He visited her, once, at Yale, but it was too weird. They almost kissed again, but they were interrupted by a naked guy passed out on the corridor near her dorm room. It was mostly when he was summoned to Hartford, for family obligations, that they saw each other. It seems that Military School had straighten him out, according to his father, and his presence was requested more and more. That was one of the motives that he wanted to go to University of Maryland, because he didn't want to be so close to home. He and his parents did better with the distance between them, he argued.

They had their first fight when she told him about the end of her first year at Yale, and the biggest mistake of her life: Dean. He almost flew over to punch him, when he heard about the affair, but it seems that Jess beat him to it. He almost sent Dean to the hospital, after Lindsay confronted Rory and the affair was made public. What Tristan still didn't know was what made Rory do a stupid, stupid thing like that.

The only one who knew the real reason was Jess, and Rory made him swear he'd never tell anyone. Tristan didn't speak to her for almost a month after hearing it. Little did he know that he was the reason that Rory did that stupid, stupid decision and slept with Dean. It all happened after she heard, through the grapevine, of course, that he was seeing someone in Washington.