I am a literati fan for life, but I just had to write this story, because I love writing about the perspectives of other people. This is about Dean's relationship with Rory. It takes place a few years after the series finale and it's in his POV. Enjoy!!
I can't handle this anymore. I got home from work today, and I saw her. I knew that she had moved away, but I was hoping that she would never come back. That was just a stupid idea, I guess, because I saw Rory Gilmore again. And all of those feelings came rushing back just like I was in high school again. I thought that I had gotten over her. I've had a few girlfriends over the years, and I figured that I could move on. How can I still be in love with someone who clearly will never want to be with me? I know that I was a pretty good boyfriend. I was her first everything, and I guess that's something to be proud of.
Let me start back to when I saw her for the first time. She had dropped her books, and was looking up at me with a look of amazement. I stared into those beautiful blue eyes for the first time, and I felt something that I'd never felt before. Rory Gilmore had me way before hello.
After that first day meeting her, I couldn't stop thinking about her. Once I finally thought she might be interested, I decided to make my move. It almost broke my heart that she didn't say anything, but once I started to walk away, she called my name. It was one of the best days of my life.
Our first kiss was in Doose's store, where I worked. It was just an impulsive decision. I don't even know what I was thinking. She said "thank you", and ran out of the store. I think that it was the cutest thing ever, even though I found out later that she was embarrassed by it.
Everything in our relationship was great. She was doing really well in her new, fancy school. The only problem that there was this one guy that was harassing her. I hated to see her hurt, so I was getting kind of annoyed at him. I finally met him one night at her school dance. His name was Tristan, and he was an arrogant little jerk. I soon realized that he wasn't being mean to her just because he was some screwed up kid who liked to bully her. He had a crush on Rory. I didn't know how to handle that-what was I supposed to do? Beat the crap out of him? Well, I almost did, but I stopped myself for Rory's sake. I wasn't sure if she liked him, and even if she did, I didn't want to believe it. Besides Tristan, everything was fine. I knew for sure that I loved her, so on our three month anniversary, I told her. I thought that she would respond back the usual way-with an I love you, too, Dean, and we'd kiss some more. It was then that I found out that she didn't love me, so we sort of broke up.
It was very weird not being with her. However, I could tell that she still liked me, especially when I saw her running away from my house after harassing Clara for information about me. I drove to her school, and saw her with Tristan. I knew that I had blew it, she was with the jerk now. The amazing thing was that she ran up to me, and finally told me that she loved me. Now I'm not sure if she said that to try to ignore her feelings for Tristan, or if she actually loved me. I'll never know. The problems with Tristan definitely didn't go away. They were in a play together, and he was her Romeo, meaning that they had to kiss in the play. I went to watch the rehearsal, and that caused some angry words between Tristan and me. I could also tell that Rory was definitely trying to hide her feelings for Tristan. Shortly after, Tristan had to go to military school. I still believe that if he had stayed, our relationship would've definitely been over. Our problem was solved by it simply disappearing.
However, the relationship didn't stay perfect. I never believed that I could hate someone more than Tristan DuGrey, but I can. Jess Mariano came to town, and screwed up my whole life. Rory and Jess started off friends. I don't know what it was, but I didn't like him from the start. I could already tell that he was bad news. I don't know what Rory saw in him. They would always discuss some weird books that I would never be able to comprehend. Besides the fact that I didn't approve of him as one of her friends, things were pretty much okay. I soon figured out that he definitely liked Rory. I told myself that that was the drag of having such a beautiful girlfriend, other guys are going to like her, right? I did my best to ignore him. Then he crashed Rory's car, and hurt her. I could never forgive her after that. It also showed that she had to like him too or why else would she be spending so much time with him? Luckily for me, Jess went to New York. Again, our problem was solved by it disappearing.
Jess did come back, though, and it was worse than last time. This time, they weren't friends. I saw some of the same symptoms that she had had with Tristan. On the outside, she hated him, but on the inside, she wanted to be with him. Bad. Again, I ignored it until it got glaringly obvious. I had to stop this. I couldn't stay with a girl who treated me this bad. At the dance marathon, she kept talking incessantly about how annoying he was. I couldn't take it anymore, so I let go of her. And I regretted it for the next few years.
Sure, we became friends after that, but it wasn't the same. I knew that she was with him, and I couldn't stand it. Once I realized that we were never going to get back together, I decided that I had to move on. I met Lindsay. She was gorgeous and amazingly nice. One day, I was having a particular bad day, and I just impulsively asked her to marry me. I thought, why not? I could learn to love her. It was obvious that she was totally into me. That was so wrong. I'd always prided myself on being the nice guy, and doing this to Lindz just put me down with all of those other jerks who treat girls awfully. Lindsay was an amazing girl, and I shouldn't have done to her what I did.
I knew that Rory and Jess were long over. Lindsay was being totally overbearing and controlling of me. Rory and I talked a lot, and I realized that I had never fallen out of love with her. So, one night, we took our relationship to the next step. The night that I made love with her is a night that will always stay in my memory. What hurt was that Rory just packed up and went to Europe. She left me this note, telling me that we couldn't be together because I was married. It was just my luck that Lindsay found the note. That became the end of my marriage, and I didn't even have Rory.
Of course, Rory and I did end up getting back together. But it wasn't that great of a relationship. All we really wanted was to get physical with each other, and it was hard enough finding space for that as it is. One night, I was supposed to pick her up at her grandparents' house. I saw her, looking extremely gorgeous in party clothes chilling around with all of these rich guys. At that moment, I realized that I wasn't good enough for her, and I would never be good enough for her, so I broke up with her, a decision that I still regret today. Maybe it was for the best. She obviously liked one of the guys there, Logan, because I heard that they were together for a few years.
All of these problems with us led me to one conclusion. I was the solid, dependable guy who she could rely on. But the other guys, Tristan, Jess, Logan-they were all more exciting than I could ever be. I was just the boring boyfriend. But Rory needed more, she needed a challenge, she needed someone who could turn her life upside down. And I guess that I'm not the guy that can do that.
I looked up, and I realized that Rory had seen me. We stared at each other for a while, and then she walked over and gave me a hug. She said, "Dean! It's great to see you. Do you want to go get a cup of coffee?"
Normally, I would've said yes. But that wouldn't help me get over her. I told her, "Rory, it's really nice to see you, but I just can't. I really need to get over you, and you're not helping."
She looked so concerned, "Dean, I'm so sorry, I didn't know…"
I smiled at her, "No, Rory, it's okay, it's not your fault. By the way, congratulations on your engagement."
Her face immediately colored, "How do you know?"
I said, "Rory, if you're going to wear an engagement ring, you have to expect others to talk about it. So, who is it?"
Suddenly, Jess walked out of the store we were standing in front of. His expression darkened at the sight of me. He said shortly, "Hi."
I nodded, "Congratulations, Jess."
"Thanks. Come on, Rory, let's go meet your mom."
She replied, "Right. Well, Dean, it was really nice to see you."
I hugged her goodbye, and as I did so, I felt some of my feelings released. I could do this. I could move on. There were other girls in the world besides Rory Gilmore, right?
Thanks for reading!!! Please review and let me know what you think!!