AN: This is my first Gilmore Girls fanfic. You'll have to excuse me if I'm not completely true to the characters. Anyway I figure I should put my disclaimer in here now so here it is: I don't own anything except for in my head and my dreams, then I wish I owned Milo Ventimiglia.

So here goes nothing. Just let me know if it completely sucks and I'll do my best to try to fix it.

Chapter 1

Rory woke up early to her phone ringing. She had been away from home following Obama for about two months. She checked the caller ID before answering only to see that it was her mother calling.

"Hey, mom. It's only 8 a.m. where I am. I don't function well at this time in the morning."

"Dearest child of mine, I have exciting news. I can't believe you abandoned me after so long to go chasing after some married politician, but I guess I understand."

"What is so exciting that you have to guilt trip me about taking this job?"

"Are you fully awake now?"

"Yes."

"Good. Now, you didn't get up to get coffee or anything did you because if you did you're probably going to end up dropping the cup and spilling it everywhere."

"Relax. I still haven't gotten out of this nice, soft, comfy bed in this wonderful hotel I'm staying at in Philadelphia."

"Okay, are you ready for the news?"

"Yes."

"Okay. Last night after my Friday night dinner that I had to endure alone, Luke asked me to marry him."

"What'd you say? But didn't you guys just get back together?"

"Yes, Rory, we did just get back together. You really want to know my answer?"

"Hello, do I sound like some random stranger who doesn't care about your life?"

"I said yes. Now guess who I want to be my maid of honor?"

"Let me have a few guesses. Me."

"Yes."

"Wow. I can't believe it. Of course I'll be your maid of honor."

"Okay, sweetheart, I'll let you go back to sleep now."

"Bye, mom."

Rory flipped her phone shut and put it back on the nightstand. She tried to go back to sleep, but with the exciting news about her mom and Luke, she just couldn't. They really deserved this. She couldn't think of two people who are more perfect for each other.

She decided to go ahead and get out of bed. She looked over at Sarah, now one of her best friends. Where ever they had to go, Sarah wasn't far from Rory. With today being a Saturday and not having to do any work, they had decided that they'd go explore the city.

Rory got up and grabbed some clothes from her bag. She went to the bathroom and closed the door. She took a quick shower and decided she needed coffee now. She left the bathroom only to find Sarah ready to go.

"Hey, Rory. I was wondering if you were ever going to come out of there."

"Well, here I am. Let's go find food and coffee first. Then after breakfast we can go look around. I actually have an old friend who lives here and works at a publishing company. I'd like to go see him today."

"Okay, well, so long as we actually do more than eat and catch up with your old friend then I'm fine. Maybe your friend can show us around if he's not too busy."

"Maybe. I don't really know if he's even going to want to see me now. Last time we met up I kind of broke his heart I think."

"Aw. Rory, what am I going to do with you? So, how did you meet this guy?"

"His mom sent him to live with his uncle who runs this diner that my mom and I go to practically every day. Anyway, we were friends for a while and then my boyfriend at the time broke up with me and Jess was there to pick up the pieces."

"Sounds like he's a good friend then. So after your boyfriend broke up with you I guess you and Jess started going out."

"Yup. That's pretty much what happened. We ended up breaking up because he decided to go live with his father, who abandoned him, and we didn't think we could do long distance. Toward the end though, things weren't going so great. I've only seen him a few times since then, but we're on speaking terms I think, or at least we were last time."

"Hey, it sounds like this guy really liked you."

"That's an understatement. The time before last time I saw him, he was getting his car from his uncle, who had stolen the car, but it broke down before he could even make it out of Stars Hollow. That time he practically avoided me up until right before he left. That was when he just tried to make me stop running from him and stand in front of him or sit down long enough for him to tell me that he was in love with me."

"Wow, he had it bad."

"I think he might still feel that way about me."

"Why?"

"Last time we met up, he sort of kissed me."

"Okay, no more on the subject of this guy named Jess that I haven't even met yet. I can tell you're starting to get a little uncomfortable. So, I heard you on the phone this morning."

"Yeah, my mom called me and told me that she's engaged now."

"Wow. Who's the guy?"

"His name's Luke, he's Jess' uncle."

"Oh, the diner guy."

"Yup. Nobody could make coffee like Luke."

They had left their room a while ago and were now walking into a café. They sat down and ordered their breakfast. They didn't talk about anything while they ate.

After they were done and had paid their bill they started talking again.

"So, where should we go first?" Sarah asked.

"How about we go see my friend, Jess first. He might be able to give us a few suggestions as to what we can do the rest of the day. I almost wish it wasn't Saturday."

They hailed a taxi and Rory told the driver to take them to Truncheon Books. Fifteen minutes later they pulled up outside the building and got out of the taxi. Rory paid the driver and they walked in.

Rory spotted Jess immediately. He wasn't really paying attention to who had just walked into the room. He was busy talking to one of his coworkers. As soon as he was done talking to the person he looked in the direction of the door. He seemed like he was frozen in place for a few moments and then walked over to them.

"Rory, what are you doing here?"

"I'm following Obama. With it being Saturday we weren't doing anything and decided to come explore the city."

"It's really good to see you. Are you going to introduce me and your friend here or do we have to guess each other's names?"

"I was getting to that. Jess this is Sarah, Sarah this is Jess."

Sarah stepped forward and shook Jess' hand saying, "nice to meet you."

"You too."

"So, Jess, do you have anything to do for the next few hours?"

"I actually took a half day off. Your mom told Luke that you would be in Philly, Luke then told me and gave me the name of your hotel. I was actually going to go see you."

"This plan worked out pretty well now didn't it? We were actually going to ask you to join us for the day if you weren't busy."

"I'd be happy to spend the day with an old friend and get to know somebody new."

"Thanks, Jess."

"No problem. Hey, Matt, Chris, I'm gonna go now. If that's okay with you."

` "Sure, go have fun. Take the whole day if you want, we don't have enough to do here to keep us busy," one of the other guys in the room yelled at Jess.

"I guess that means you have me all to yourself for the day."

"I guess so. Come on."

They walked around the city for a few hours just talking and occasionally they would walk into a bookshop or something. Finally at around 12:30 they walked into a restaurant for lunch. So far, Sarah and Rory absolutely loved the city. Jess was a great tour guide in spite of him not really being a people person. After lunch Jess had to get back to work because he didn't trust his coworkers to actually do any work with him not there. They made it back to Truncheon. Sarah went ahead and walked outside to get the two girls a taxi and left Jess and Rory to talk to each other. They waited till Sarah was outside before they said anything.

"So, thanks for today, Jess."

"No problem. Rory, what was your actual intention of coming to see me today?"

"Jess, I told you exactly what it was when I walked in here this morning. Why are you interested in that anyway?"

"It's just that last time you came to see me, you didn't exactly not have an agenda. I was just wondering. What are you doing tomorrow? I was thinking if you wanted to we could go for lunch somewhere and catch up."

"Tomorrow's Sunday so I don't have work to do. Sure. That sounds great. I've really missed you."

"I think you've said that a million times today. But, it's good to see you too. So, do you have a number I can call you at?"

"Oh, yeah, hang on a second." Rory took a pen and a peace of paper out of her purse and wrote her cell number on it. She then handed it to Jess, "here you go. I guess I should go out there and go back to the hotel before Sarah runs in here and drags me out."

"I guess so. I had fun today."

"So did I."

They stood there not really saying anything for a few minutes. Finally Jess pulled Rory into a hug and said, "I really missed you. Next time don't wait so long before visiting."

"I'll try, but it might be a while."

Rory didn't want to leave Jess, she didn't even want the hug to end, but alas all good things must come to an end. Before she couldn't keep herself from doing so she pulled away from him and meant to kiss his cheek, but at the last possible second he turned his head and she caught his lips instead. It was better than any kiss she'd ever had. Before the kiss evolved into anything more she pulled back and walked away.

When she got outside Sarah decided to question her, because she had seen what had happened.

"I thought you told me that you guys were just friends. If that's true then, what was that that I just saw?"

"Nothing."

"Oh, yeah. You just kissed a guy that you claim that you don't have feelings for. How is that nothing?"

"I don't know what just happened. I meant to get his cheek but he turned his head and I got his lips. Would I be lying if I said I didn't like that kiss?"

"Rory, honey, would you even be here if it hadn't been for him? I mean, he pulled you out of that ridiculous hiatus. That was only because at the time, he knew the old you the best. Could you imagine what your life would be like if he hadn't called you out on how much you'd changed that night?"

"I would probably still be living with my grandparents and I probably wouldn't have ever gone back to Yale, or become a journalist so I wouldn't have met you. I wouldn't be able to stand that."

"See, you admit that you wouldn't be here without him, but when you were talking about what I just saw, you started blushing so hard."

"No, I wasn't."

"Yes you were. I bet he's the only one that could get that shade of red out of you too."

"Okay, fine. Yes, I was blushing. By the way, Jess is taking me to lunch tomorrow, so you can hang out with some of the others if you want. We were just going to catch up, you know, tell each other what's been happening in the past few years."

"OK. Thanks for the warning. I'll think of something. You just have fun with this guy. You seemed really happy today. Happier than I've seen you in a long time."

"I was. I wonder what I should wear tomorrow. I mean after the kiss, he's probably going to think it's a date, but it's not. So what do you think?"

"Maybe just wear a good pair of jeans and a nice looking top, not a skirt and blouse, unless it's not that dressy."

"What would I do without you, Sarah?"

"I don't know."

Before they knew it, they were back at the hotel. They decided to just order room service for dinner and watch whatever was on T.V. That plan worked out great. The next thing Rory knew, she was answering her phone.

"Hey, mom."

"Hey, kiddo. So, what's going on with you?'

"Well, today, I met back up with Jess. This time it wasn't an accident. You knew I was in Philly this week so you told Luke who then told Jess and gave Jess the name of my hotel."

"How'd you know?"

"He told me. But, um, this time it wasn't him coming to me, it was me coming to him. You see, Sarah and I needed a guide to show us around the city and I hailed a taxi and we went over to Truncheon. Thank god Jess was there today or we probably wouldn't have been able to learn our way around seeing how I've only been here once and that was at the open house for Truncheon and Sarah's never been here in her whole life."

"Wow. So, did he say anything about last time you saw each other?"

"Surprisingly, no. However, I think he might bring it up tomorrow. He and I are having lunch just to catch up and to talk. You know, normal friend stuff. Except it won't be just friend stuff because today I kind of kissed him."

"You what?!"

"Relax, mom. It was an accidental kiss. I was just going to kiss his cheek when at the last second he turned his head and I got his mouth instead. Would it be a bad thing if I said I liked it?'

"Oh, sweetie. I don't know what to tell you except you guys had better sort this thing out before my wedding because he's the best man."

"Really, it had to be him? Oh well, at least I won't have to dance with Kirk or TJ."

"True. That's the bright side of this."

"Hey, mom. It's getting kinda late so I'm gonna go. I'll talk to you tomorrow and let you know how my lunch with Jess went.

"OK. Talk to you tomorrow."

Rory then hung up her phone and laid it on the night stand and went to sleep.

AN: Like I said, this is the first fanfic that I've written for Gilmore Girls. I would appreciate your reviews, please no flames. Remember the more reviews I get, the longer the story is, also the more good reviews I get, the better the story might end up being. Constructive criticism people, you gotta love it.