A/N- This is my first Gilmore Girls Fan Fic and I wasn't sure how to write this first chapter. I wanted to give Rory a friend while she was gone so I did. She kinda talks a lot in this chapter but there was no other was to get all the Jess stuff out for Kylie.

Disclaimer: I don't own Gilmore Girls. I do however own this plot.

Author's POV

Rory sat on the plane studying her itinerary. She was already missing her mom, she felt like she had lost time with her and that it had been too soon to say good buy.

"Is this seat taken." Rory looked up to see who had interrupted her thoughts. Standing there was a girl about her age with light brown hair and brown eyes.

"No," she replied." I'm Rory"

"Hi, I'm Kylie. Are you a reporter?"

"Yeah I just finished college. What about you?"

"I'm just out of college too and I'm a reporter. Looks like we have some stuff in common, where are you from?" Kylie seemed nice, Rory was relieved to have met someone she had stuff in common with.

"Stars Hollow, Connecticut. Its one of those tiny quirky towns where everyone knows everyone. So small that if you talk to the right person, in ten minutes you'll know all the gossip from who's fighting with who to who is living a double life." Rory replied smiling as she talked about her hometown. "What about you?"

"That sounds like a fun place to live. I never knew what small towns were like I lived in New York until I went away to college. I hated it there I always wanted to live in a place like Stars Hollow, or at least know my neighbor. I think I saw my neighbor back in New York once and when I smiled and waved at him I think I heard him growl." Kylie said laughing. "So where are you looking forward to going most?" She pointed at the itinerary.

"I don't know. I haven't been many places so everywhere I guess. What about you?" Rory liked Kylie, she could already tell they would be friends.

"That's an easy one, Philadelphia."

Rory's eyes widened in surprise. "Did you say Philadelphia? I didn't see that on the list! Why do we have to go to Philadelphia?" she said frowning.

"What's wrong with Philadelphia? And you?" Kyle asked clearly confused.

"My ex-boyfriend lives there. Normally not so bad but we have a pretty rocky past, and things didn't go so well last time I saw him." Rory surprised herself by being so open but she knew already she could trust Kylie.

"What happened?"

"I'd have to start from the beginning for you to get all of it."

Kylie leaned back in her seat. "I've got lots of time and I'm a great listener."

"Okay. Well when I was seventeen Luke's nephew Jess came to town. Luke owns the diner in town and feeds me and my mom pretty much every day. My mom's far from a chef. Luke was also like a father to me. Eventually he and my mom started dating but that was after Jess. When he came into town he was hated by basically every one but, there was just something about him. He was different than any one I had ever met, he was so smart. You never saw him without a book in his back pocket. I found that I liked him as more than a friend which wasn't good because I had a boyfriend, Dean. He hated Jess more than anybody.

"Jess was great but the thing was he left me three different times. The first was after we got in a car accident in my car that Dean had built for me, Jess was driving. He went away and then he came back after a week or two and a visit from me in New York. Yeah, I ditched school to go and see him in New York because he hadn't said good bye when he left. He came back the day of my mom's best friends wedding. I saw him standing by a river. He told me he had come back, I asked why and he said he just wanted to. He was looking at me right in the eyes and I could tell it was because of me. I kissed him. And yes I was still with Dean. In fact I was at the wedding with Dean and I still kissed him. I was in Washington for the whole summer so I didn't have to see him. I tried to write him but I didn't know what to say. When I got back he had a girlfriend. Weeks passed and we pretty much ignored each other.

"At the town Dance Marathon I was dancing with my mom and he came in with his girlfriend and basically stared at me all night. I couldn't take it anymore. Dean was dancing with me then because my mom's shoe broke and she went to get it fixed. I was talking about how annoying Jess was and Dean got mad, he yelled at me and broke up with me saying to me and Jess that now we could be together that it was obvious we liked each other. So Jess and I started dating we fought at times but we always made up. After we had been dating a few months we went to a party. He seemed upset and when I went to find him, he was upstairs alone. We started kissing and he acted like he wanted to have sex but I didn't want to, not there at some party. I stopped him and then he seemed like he was mad. I was upset and crying I told him I didn't know what I'd done. Then I ran out the room and he came after me saying that I hadn't done anything. As I was running out I bumped into Dean and his new girlfriend. He asked what was wrong then Jess caught up with me and saw I was with Dean, he mumbled figures under his breath as he walked by. Then Dean ran after him and punched him. They fought and wrecked the house. I didn't see Jess again until he came back to Stars Hollow a year later. Well guess what he tells me? He says he loves me and then runs back to his car and drives away. I thought that would be the end of him, I was wrong. One night Dean was dropping me off at my dorm, he had rescued me from a party. He was about to leave when Jess shows up. I sent Dean home then Jess asked me to come away with him. I said no.

"Then years pass, I temporarily dropped out of Yale, was living with my grandparents, fighting with my mom. And one night I'm getting out of my car (at my grandparents) I turn around and there's Jess. He said he wanted to give me something and he did. A book written by him. He asked if we could have dinner, I said yes. We meet the next night and as we're about to leave my boyfriend shows up. He comes with and they fight. Jess walked out and I went after him. He asked what I was doing. Why was I fighting with my mom, why was I living with my grandparents, why was I with Logan and why did I drop out of Yale. I couldn't tell him because I didn't know myself. He saved me. I fixed everything. Then I got a flyer for an open house at Truncheon Books which is where he worked. I went. I kissed him. I was still with Logan even though he had cheated on me. I told him that and that I loved Logan. He was upset and I know I really hurt him. That's why I freaked out." Rory finished. She had just told Kylie everything about her entire relationship with Jess. "So what do you think?"

"You should go see him. You know where he works. I'll even come with you." Kylie said encouragingly.

"Okay. I don't know how I'll face him but, I never will unless I do."

A/N- Okay, so what did you think? I've already posted the next chapter I think it's better than this one. So if you didn't like this one don't give up on it yet. Oh and please review. If you have any ideas that you would like me to include let me know and I'll try to.