Chapter 7

The next day Rory met Jess at the diner as planned. "Uncle Luke, I'm going with Rory, you got it covered here?"

"We got it Jess, just go." Lane answered for Luke.

They walked outside and Jess took Rory's hand and led her to the bridge. "I know it's a little cold but I figured this was as good a place as any, we do seem to do a lot of important talking here. But if you get too cold let me know."

"No, this seems perfect. There are a lot of memories here aren't there."

"Yeah. I never did tell you about the swan that attacked me here did I?"

"The what?!?"

"Ok, you remember the night that I was supposed to have dinner with your grandma and showed up with that black eye?"

"Yeah, I know you didn't get it from Dean now, so what does this have to do with a swan?"

"Ok, so I was out here and this swan beaked me right in the eye." Rory burst out laughing. "See this is why I lied and said it was a football. Anyway, later that night after I told Luke and after he stopped laughing we came out here to try and find it and it tried to attack us again. I'm telling you the birds are evil."

"Wait," Rory said still laughing "you're telling me that the reason you showed up to my grandmother's dinner with a black eye was because a swan beaked you in the eye?" She could barely get it out this she was laughing so hard.

"Yeah, yeah, well at least now you know."

"Oh my. Jess, you do know I'm going to have to tell my mom about this and we're going to mock you for life right?"

"Yeah, I figured when I told you it was only a matter of time before Lorelai found out." Jess groaned.

"Well, thank you for being honest." Rory said still giggling a little. "Ok, I guess that's as good a place as any to start. Why did you feel you needed to lie about that Jess? Sure I would have mocked you, but it would have been better than getting into that huge fight."

"I didn't think you'd believe me. And the entire time we were together, and part of this was my own fault, but I felt like I had to prove myself to everyone. Prove that I was good enough to be your boyfriend. Everybody loved Dean so much and you were the town princess dating the golden boy. Then I came along, the town hoodlum and everybody just expected me to hurt you, expected me to not be good enough for you. I hate that they ended up being right."

"I think sometimes when all we expect from people is failure, they can't help but comply."

"Yeah but it still wasn't right. And I didn't handle things right. I cared about you so much, I loved you even, but it always just been me to deal with my problems, I didn't rely on anyone else. So when I failed out of school and then Jimmy came, I just panicked and did what I do best, ran away. That stupid fight we had at that party didn't help either. Though that was mostly my fault too. I shouldn't have pushed you and you were right to get mad. And I shouldn't have punched Dean."

"Well, he wasn't exactly Mr. innocent either."

"Yeah but I shouldn't have left without saying anything. And I shouldn't have kept calling but saying not anything, but I didn't know what to say. Then when I came back and blurted out that I loved you? That was so stupid. Even though I meant it, I couldn't spring that on you, and after all that asking you to run away with me, I was an idiot. Nothing about how I handled us was right Rory, nothing."

"You're right. Well, mostly. I knew you had emotional baggage, I knew you had problems trusting people, yet I expected you to be able to treat me like a normal boyfriend. Sure I wanted you to let me in and tell me what was going on, and you should have, but I shouldn't have expected too much. And then just when we started to be able to move past all that, just when were approaching friends again, I go and screw it up myself. Whether you had hurt me in the past or not, you didn't deserve that. You didn't deserve me using you against Logan, especially when you couldn't stand him, it wasn't fair to you."

"Rory can I ask you something? Why did you get back together with Dean? Why did you sleep with him when he was married? That doesn't sound like you."

"I think I was confused. I was just getting to where I was completely over you and then you show up again and ask me to leave with you. And I remember having this conversation with Lane about how it was exciting and unpredictable and part of that was thrilling and I wanted to do but it was also scary. I had no idea if you would mean it later or if you would just leave again. And then we started talking about Dean and how he treated me so well and how I screwed that up. Then Dean and I met up again and he said his marriage to Lindsey wasn't working and I just, I think looking back that it was like I was trying to get back at you and prove to myself that Dean was a better choice. I tried to see through the infidelity and my true feelings and convince myself that he was right for me. So I forgave the fact that he used me to end his marriage and the fact that he told me that it was a mistake and that he didn't even know if I would stay with him because I had dumped him before and tried to make it work. But he wasn't willing to fight for me. He came to my grandparents house where they were throwing me this party, trying to introduce me to eligible guys they thought were suitable for me and he freaked out and broke up with me saying he would never fit into my life. I gave him no indication of that, he just broke up with me. Logan was there and he and his friends helped me get over it by drinking and being ridiculous. I think that's when I started to really like Logan. Does that make sense? Does that answer your question?"

"I think so. It was like Dean was what I wasn't, but he still wasn't the one for you?"

"I guess so."

"Ok, so Logan, what's the story there? I'm sorry, but he doesn't really seem your type. We used to make fun of guys like him".

"I didn't know this was going to be talk about all of Rory's exes day, but ok. When I first met Logan I thought he was self entitled and spoke to people like they were beneath him. Like he did that dinner when you met him. That was the Logan I first met. But then I was doing this article for the Daily News that involved this secret society that he was in called the Life and Death Brigade. He showed me how to just have fun with life. How to not stress out so much and at first, how to just date. We weren't exclusive at first but then I couldn't handle it so I told him I was out. He decided instead to be exclusive. That's when things got tricky. He took me to his parents house when his sister was announcing his engagement and his mom and grandfather attacked me and said that I wasn't good enough for him. Then his dad tried to smooth things over by offering me an intern position at his paper but then during my review told me I didn't have it. I went to a party with Logan to celebrate his sister's engagement and I couldn't handle it so we stole a yacht, and got arrested."

"You got arrested! Wow Gilmore, you managed to get arrested before I did, bet this town didn't see that one coming".

"The town doesn't know. It happened in Hartford and Mom and I kept it a secret, well except from Luke. Anyway that's when I decided to not go back to Yale. I figured if Mitchum Huntzberger didn't think I "had it" then what was the point of being a journalist. Logan didn't really know any of this but when I told him, I don't know he tried to talk me out of it but not really. Logan's life was all parties and drinking and life and death stunts. It was thrilling but somewhere down the road I lost myself. That was about the time you showed up, doing more with your life than I was. It woke me up. Here's this guy no one but me and Luke thought would amount to anything and here I am, the town princess supposed to conquer the world and I dropped out of school, moved in with my grandparents and joined and worked at the Daughters of the American Revolution. So after you left Logan and I got into a huge fight in the middle of that bar. So we took time off which apparently Logan saw as a break up which I didn't even realize until his sister called to say she was sorry about it. Then he weaseled his way back into my life, apologized and I took him back. Why? I really don't know I guess his thrill was still appealing to me. And then I go to his sister's wedding and I found out that he slept with almost the entire wedding party during the time we were apart. And he justified it by saying that he thought we were broken up and I bought it and we were together again until he asked me to marry him. Logan was good to me at times. He bought me nice things and took me nice places. But I think I let that overshadow that he didn't appreciate me. And he wasn't willing to fight for me either, not in the end anyway. He did at first but then it was, get married or that's it. It had to be under his time and rules."

"So, why did you give both of them, Dean who didn't fight for you used you and Logan who cheated on you and thought you could be bought with expensive gifts, why did you give them a second chance but not me? I know I left and I know I was stupid, but I did fight for you Rory. Maybe it was too little too late, but I fought for you. Not only to be with you but when you weren't at Yale, I fought you yourself for what was best for you. And it got you to go back didn't it? All I ever wanted was for you to be happy. But you weren't happy being smothered by Dean and you weren't happy being toted around like arm candy with Logan. And I guess that's what hurt the most. When you told me that you loved this jerk that cheated on you and treated you like something he owned, it really hurt. I thought she'll love this jerk and give him chance after chance but she still won't forgive me for hurting her all those years ago. I know I hurt you, but you hurt me too Rory. And that's why I thought we needed to talk. If anything happens between us, even if we just become good friends, I don't want all of this to come up later in a fight or because it burrowing deep inside of us. So I guess that's my last question, why didn't I get a second chance like they did?"

"Jess, I know I hurt you before. And I felt like a jerk afterwards. That's why I never called you afterwards. As for why I never gave you a second chance, I don't honestly know. I think because you hurt me deeper than either Dean or Logan did. And not because what you did was worse, but because I felt more for you. You were the unexplainable love to everyone else. Dean made sense, he was as you said, the golden boy. He was good to me and made me a bracelet and a car. And Logan was the nice rich boy who was misunderstood and really a good person. But you were the hoodlum who just wanted to corrupt me in everyone else's eyes. You had to really know me, and really know you to understand us. You loved books and were so smart and you didn't care that I was the town princess or that I would go to Yale and make you feel dumb, you wanted me to have everything I wanted. So I think I knew that if I let myself, I would fall harder for you then Dean or Logan and that was scary. I let myself listen to the town, even to my mom and Lane because while they knew me, they didn't know you, not at the time. I think the only person outside of us who got it was Luke, which is funny since it took him so long to get that he and my mom belonged together, but us he got right away. So, I guess that's it, I knew a second chance was a risk for me getting hurt more than ever, not because you were worse than the other two, but because I loved you more."

"I guess I can accept that. So, now that I grilled you, do you have anything you need to ask me, or did we cover all that before?"

"Just one thing. If I wasn't with Logan that night in Philadelphia, or if I didn't tell you I was, what did you want to happen? Was it just going to be a physical, one time thing? Or did you want more?"

"Rory, I've always wanted more with you. Yeah, the physical is nice, we were always good at the kissing part, we said that from the beginning, but it was more than that, it always was. I'm glad you told me you were with Logan. I hated that you were with him, but I wouldn't have wanted to do something with you and then find out later it would have just been a one time thing. I think that's why I got so mad, why it hurt so much, I let myself think we could try again."

"Ok, so now that we've gone through six years worth of our past and how we screwed it up, where do we go from here?"

"I meant what I said before, I think if we rush trying to label it too quickly, trying to define it and put a set of rules down for it, it will fail. And trying to be us again when we won't, we can't see each other very often? Its stupid and asking for failure. So lets just see what happens. But we have to be honest with each other. We have to communicate and really try. Because eventually, yeah, I hope this goes somewhere beyond friendship. But that can't happen if we don't keep talking and emailing and writing letters."

"I think I would like that. I need someone to write too besides my mom and grandparents and Lane. And it will make things easier in March when Mom and Luke get married. Hey, the fact that we're going to be step cousins doesn't bother you does it?"

"Oh geez, can we not think about or talk about that please?"

"Haha. Ok. Jess, I'm glad we had this conversation. And I hope this goes somewhere else too. So as my friend, will you go to Friday night dinner with me, Grandma is planning this celebration of my being in town that she didn't want to interfere with Christmas and she said to invite you."

"Oh geez. You want me to go again? You're grandparents are going to think we're together, and I know your grandmother invited me this time, but I think she was just excited about the wedding, no way that woman wants me in her house, around you again."

"Look at it this way, if my grandparents get to know you now, as one of my friends, then they'll like you more if this does ever go anywhere else. And she'll get suspicious if I don't invite you and mad if you turn it down. I know, since its in my honor what if I invite Lane and Zach to come? Then its not like we're together just that my three friends from Stars Hollow are there."

"Fine. You know how hard it is for me to say no to you. Geez we've been here for like three hours. We better get back before I get accused of kidnapping you."

He held out his hand to help her get up and they walked back towards town, both with slight smiles on their faces.

Author's note: I know this one was a lot longer than the others, but I felt it was needed. I always thought that if Rory and Jess talked about stuff things would have gone differently. I hope it wasn't too deep ;) Hope to update soon and hope you enjoyed this, let me know what you think!