Disclaimer: I don't own Gilmore Girls

Jess's POV

I woke up on the floor with my head on the bed. Rory woke up at the same time as me.

"I'm going to go get some coffee" Rory got out of bed and walked out the door.

-------------------------

Rory's POV

In my half sleeping state I ran into a boy. He was tall a lot taller than me. I think he's around 16.

"Hey" he said.

"Hi I'm sorry I wasn't paying attention to where I was going it's my fault"

"Don't worry about it" he smiled at me "Hi"

"Hi"

"I'm Dean"

"Rory"

"Rory that's a cool name"

"It's short for Lorelai" I smiled.

"Shoot I don't have any cash I got to go get some from upstairs it was nice meeting you" I started to walk away from the line.

"It's ok I'll get it" he stopped me.

"Uh thanks I'm sorry but how old are you" I asked.

"14"

"You're tall" I said wondering if I should trust this guy.

"Would you like to see some ID" he laughed.

I nodded and he took out a school ID.

"I feel like an idiot" I mumbled.

"What do you want" he asked.

"Uh regular coffee" I said.

"Two regular coffees" he said to the mad behind the counter.

Minutes later the guy handed us the coffee and Dean paid.

A/N: I really hate Dean he won't really be a major character he's also going to be extremely ooc just because I can't stand how he was on the show and I wanted him to help out a little.

"Would you like to sit down" he asked.

I nodded and he led me to a table in the little café inside the hotel. I sipped my coffee quietly not looking at him at all. I couldn't stop thinking about Jess. Do I really love him?

"Are you ok" he asked.

"Yes" I lied. I didn't feel like lying today. "No" I added.

"Wanna talk about it" he asked.

"No" I lied again. "Yes" I added.

He motioned for me to continue.

"Ok well I like this boy and I've known him for a long time well not really long just a while a few years" I started "but anyways he's with this other girl her name is Shane and we used to be friends but then we stopped being friends and now we're friends again and I'd like to keep it that way and I don't think stealing her boyfriend would help keep it that way not that I think I could steal him I mean there's no way he's interested in me. I really like him I can't stop thinking about him he's engraved in my mind and it kills me to see him with her. The worst part is that he's my mom's fiancé's nephew and we have to share a room together on our little family vacation. He lives with Luke that's my mom's fiancé he owns a diner. Luke not Jess. Jess is the boy that I like."

"Wow" Dean said.

"It's complicated" I said.

"I can tell" he laughed "I think you should tell him how you feel"

"I did during a game of truth or dare"

"What did he say" he asked.

"Well I walked away he followed me then I started crying and he hugged me and I went intoa whole rant about how I don't want things to beweird and how he probably didn't care about me and then he said he did care about me and then we fell asleep."

"Well then maybe he likes you too" Dean tried.

"I had the weirdest dream I told him I loved him."

"Do you?"

"Yeah I think I do" I smiled "thanks you've been a big help."

-------------------------------------

Jess's POV

"I used to have dreams like that too eventually they stopped" Shane's voice came through the phone.

"When" I asked hoping it was soon.

"When he got his sentence" she laughed.

"Two weeks" I sighed.

"Yeah" she said.

"So tell me more about this dream you had."

"I told her I loved her that's pretty much it"

"Do you" she asked.

I thought for a second. Did I?

"Yes"

"Then go get her" she said.

"Thanks Shane"

"Tell me all about it"

"Will do" I smiled. When I first started going out with her I figured it was just a waste of time just something to get Rory jealous but she really was a pretty good friend. She helped me more than I thought she could.

I heard a noise and looked up. Rory was standing in the doorway eyes wide.

"I can't do this" she mumbled and ran out and into some really tall guy.

"I guess it didn't go very well" the tall boy said.

"Oh I was just looking for you" she smiled brightly.

"You were"

"Yea come on" she opened the door wider and let him in "Jess this is Dean, Dean this is my mother's fiancé's nephew Jess."

Ouch.

-------------------------------

Rory's POV

"I couldn't do it help me" I whispered.

"Hey didn't you want me to teach you that game 2 Truths and a Lie"

"Isn't that that stupid game where someone has to figure out what's a lie" Jess asked.

"Yea" Dean nodded.

"Sounds easy enough let's play" I smiled hoping he had a plan.

"Ok I'll go first" Dean said "I've never had coffee, I live in Chicago, I can't ski"

"You've had coffee" I said.

"Yep your turn" he looked at me like this is your chance.

I looked at Jess completely taking him in. He wouldn't like me. Why would he? I'm nothing. I'm no one. I was saved when mom burst through the door.

"How is it possible that you are already up dressed and have met a new friend" she asked.

I shrugged.

"Well new friend you have to leave we are hitting the slopes" she said and Dean left without another word.

"You guys get ready to go we'll meet you out there" mom left.

---------------------------------------

Jess's POV

"Great it's locked" I turned back to Rory who was taking off her jacket.

"Why would they lock it" she asked.

They're meddling again.

"Why did we lock them in the apartment" I mumbled. I don't think she heard me. I hope she didn't hear me.

"What was that" she asked.

"Nothing" I said quickly.

"Okaay" she walked over to her bed.

"So what's with that guy" I asked.

"Dean he's just some guy I met who helped me work through something.

Damn. I wanted to be the one to help her deal.

"Oh so you're feeling better"

"Yup"

"Good no talking in your sleep tonight" her eyes got wide and she stood up and walked around nervously.

"Jess really you can't hold that over my head" she said quickly "I mean I was asleep I didn't know I had even said anything out loud"

"It's ok Ror" I tried to calm her down "Shane said she had dreams like that all the time."

"Yea well she's your girlfriend."

"What does that have to do with anything" I asked.

"Well your girlfriend saying she loves you in a dream is one thing but just a friend that's kind of pathetic don't you think."

"What Rory what are you talking about" I asked.

"What am I talking about? What are you talking about?" She relaxed.

"What happened the night in the storage room" I said "what were you talking about." She tensed right back up and I regretted asking.

"Nothing" she walked to the other end of the room.

I'll let it go.