A/N Plan on trying to post a chapter or two a day, depending on how fast the writing goes. Please leave comments on any ideas. I have the basic outline laid out but am always interested in opinions. Hope you enjoy. I always felt this discussion was necessary.

Chapter 10 - Jess

Jess ran out of the Gazette as quickly as his legs would let him move. Once Rory gave him the opening to see her that evening he did not want to give her a chance to renege. He had already chastised himself enough over the dumb coffee. Who brings coffee to a pregnant lady, he grimaced at the idea. Of course it is a pregnant Gilmore, so there is room for deliberation. And she didn't know he knew, so bringing her tea or decaf would have just been odd.

As he turned the corner back toward the diner he ran into a tall figure. He looked up. There he stood, his old nemesis, Dean Forester. He backed up, not quite sure of what to say or what to do. He didn't need to worry. Dean spoke first.

"So you are still in love with her." Jess looked at Dean in confusion, he had said it as a statement rather that a question.

"I'm sorry?" He tried to be polite, acting as if he misunderstood what was being said. He did, but he didn't.

"I will admit, she is a hard one to get over. I blew my first marriage thinking she was the girl for me. But I wont deny it, she is special. She was just a little too much for me. She wanted too much, she was too much. Thank God I realized that. But she encouraged me to be better than I was. I think that was her charm. She assumed everyone was as wonderful and capable as she was…is. She brings you into her world and its like Hansel and Gretel in the candy house. Until, at least for me, you realize you have bitten off more than you can chew."

Jess stared at Dean, taking in the honesty in his words. He couldn't let him walk away without knowing a few things, so he decided to ask, rather than being confrontational, which had been his MO with Dean in the past.

"Wait, you and Rory got back together? I didn't know that."

"Yeah, remember the time I saw you at Yale? Well, things were just kind of starting back up."

"Wait, you were married, that's why you said you blew your first marriage. What happened?"

"I wasn't over her. Lindsey was my rebound girl and she treated me good and she was simple and wanted simple things. Rory wanted big things for me, school, a career not just a job, a future that wasn't what I had in mind. But I loved her, and after Lindsey found out about the affair, she left me. Rory and I tried to make it work, but it didn't because it was never meant to be."

Jess digested Deans words. Words he would not have ever applied to Rory. Affair was the one that resonated in his head the most.

"Wait, so why do you say I still love her?"

"I saw you man. I was walking across the street from the Gazette and you caught my eye and I saw you staring at her through the window when you thought no one was looking. And then I realized who you were staring at, and I thought, of course, I know that look. I have worn that expression. Look Jess, I am happy now. I love my wife, I have three kids and one on the way. But Rory was my first love. I will always love her. Not love, love, but care for her in a special way. But the look I saw on your face was the one I used to wear. Even after I married someone else. It took a long time to realize that I would never be what she needed, and that in reality she wasn't what I needed."

Jess was surprised at the number of words that poured from Dean. He had never been much of a talker.

"How do you know what she needed?" Jess's tone was extremely calm and polite, he wasn't challenging Dean's statement but rather, extremely interested in his point of view.

"Rory wanted the world. Maybe she doesn't anymore, but at that time she did. And I knew it from the beginning. I should have steered clear. But who can, from a girl like that. But after we got back together it was like I was getting her back from you, and I was winning, I didn't realize that you were not the enemy. But the night we ended things I realized what I was really fighting against. In my mind she was a simple girl from Stars Hollow, Lorelai had kept them away from all of the other stuff, so Rory didn't act like that. But from the cotillion I should have known. I didn't fit in her world with the rich friends and the big parties and the bottles of champagne. I wanted a simple life. I ended up going to school and got a degree and a career, I thank Rory for that. And then I met an amazing woman who is an awesome wife and mother. I couldn't ask for more. But it took learning the hard way. The Rory Gilmores of the world are few. But as you know, she is impossible not to love. The problem is whether or not she will love you back."

Jess just nodded his head as Dean spoke taking in all he was saying.

"I gotta get going man, it was nice seeing you, and I mean that. Be careful! Don't love someone who can't love you back. You will end up wasting too many years. I know."

And with that Dean walked away leaving Jess standing in the middle of the street dumbstruck. First at the fact that he had just had a cordial conversation with Dean Forester over Rory, and second over the magnitude of what he had said. He knew he would be replaying the conversation in his head for a long time. There were things he didn't know. Things he did know, and things he had yet to find out. But the one thing he was sure of was that he wanted to try. Dean said that he and Rory were not meant to be. That was something Jess knew from the first time he saw them together, he wasn't enough for the likes of a girl like Rory, even then. But the question he wanted the answer to was whether or not he and Rory were meant to be. And even after all these years, he felt the answer was yes. If they would just give themselves a chance.

But now things were a wreck; she was pregnant and there was another man in the mix. The trail of broken hearts Rory Gilmore left behind her.