A/N: First and for most I want to thank everyone who took the chance to read the first chapter of my story. I received a lot of helpful feedback that caused me to reanalyze this chapter before I actually put it out. Thank you all.

To my feedback givers:

Miriam Dickens - Thanks for the feedback. I was dying too. I was like just go with him. My friend & I argued for an hour about this. She's a R/D fan. Needless to say... I won that argument.

Magic em - I used to watch Dawson's Creek all the time. I never was a Dawson/Joey fan but was easily able to parallel Joey to Rory because the entire second season of D/C... Joey was doing the push pull thing with Pacey & Dawson... it sickened me. I just felt that this past season... actually the past 3 seasons have been Rory playing games with both Dean & Jess.

Mystyk-cryer - I'm glad that I got your interest. I hope you'll continue to read.

CaliforniaDreamer - I appreciate all the tips you gave me. I'm going to definitely work on everything you mentioned. I'm definitely trying to get the characterization thing down. I'm hoping it becomes easier as things develop.

Sarah - Glad you liked it thus far. I agree about the writers... Rory was so not in love with Dean. It was a territorial instinct I think. She always envisioned her first time with Dean... actually that's not true. I lied. She envisioned her first time with Jess because she actually talked to Lorelai about it. But it completely ruined the innocence of the character.

Dawn - I hope I can convince you otherwise. And I hope that you will like the way I develop this.

Smile1 - There's more to come. I hope you'll stick around to read it.

Disclaimer: Everything belongs to ASP & Warner Brothers. I own nothing.

I should be used to being alone by now. Out here on the road heading back to the one bedroom apartment I shared with six other guys. Had she come with me, we probably would have stayed in New York but plans quickly changed. I'm leaving this city and onto bigger things. The open road was going to be my new companion. I have no idea where I'm heading. Not a clue. If she was with me, the next few days... hell the next few months would be meticulously planned from sunrise to sunset. Every moment accounted for. That's how it was intended. I wasn't supposed to be alone again. This trip was supposed to be a shared journey of rediscovery. It was always meant to be with her... traveling alone this summer was never my plan.

Here I am alone... the only company I have right now is the sound of my radio which is fading into the background as my mind becomes a jumble of thoughts and emotions. Yet again, I am left to figure out what I could have possibly done wrong this time. Nothing. All I did was ask her to come away with me. Cliché? I know. Big time. And I'm definitely not the cliché type. Ask anyone who has spent two minutes in the same room with me. Don't even remind me of the Norah Jones reference that is supposed to be associated with that phrase... I won't allow it. I will not let that moment become something out of a sappy romantic comedy. I will never let myself or anything I say become that cliché.

Ever since we broke up... I did the growing up thing. I did the whole soul searching quest and I did change. I promise I did. I finally mastered the whole being-there-for-other-people-without-asking-questions concept she was always talking about. I swear I did. Hell I walked my mother down the aisle at her wedding to the same moron who tried to knock my head off my shoulders the night before at his bachelor party. For me that was a big deal.

You know all the altruism crap... good will towards other... all a waste of my time. Really what was the point of changing when she couldn't even be there to see it? There was no point. I did all that reinvention, finding myself crap for what... a certified Gilmore kick in the teeth that's what.

I thought that if I finally got my shit together... then we could be together. Who was I kidding? To think that I, Jess Mariano, could hold on to Rory Gilmore. I was a fool. Her exquisiteness, outside as well as in, should have been clue number one. She was... is... stunning. Her eyes were... are still... burning embers that can penetrate your skin and burn deep into your soul within a single moment of eye contact. Trust me. I should know. Her incredible intelligence, desire, and motivation destined her to be great. To accomplish amazing feats. She has. She will. And there I was failing out of Stars Hollow High, my senior year no less, working full time at the Wal- Mart in the next town over, part timing at Luke's and trying to hang onto the incandescent Rory . I must have been fucking kidding myself.

Maybe if I had gotten things right from the very beginning things would be different. She would have come with me tonight when I asked her. She'd be sitting next to me right now. She would change the station on the radio until she found some annoying 80's music. Then she would turn the volume way up and start to sing the words. I would just sit there... smiling at her and laughing. I love 80's tunes. I honestly do, who doesn't love Aerosmith or AC/DC, but really how many times can I listen to the B-52's 'Love Shack' before I want to strangle someone or break something? I tolerated it though... for her. Only for her.

We'd sit and talk about the last year. How life has really been treating us. At first she say everything was just 'peachy keen'... of course she'd only say it to quote Rizzo from Grease... but she'd still say it. Then we would dive into the real circumstances that surrounded the past year. She would rave on about Yale and the college life. I would tell her all about living in New York and my long awaited light bulb cartoon moment. After a while she would start to doze off and I could envision her resting her head on my shoulder. I'd slip my arm around her and hold her as close to me as possible without smothering her. She'd rest peacefully until I woke her when we stopped at a small diner for breakfast.

We'd go in and order... she of course would start with her coffee and probably a stack of pancakes draped in maple syrup... I'd have a super six, which any one who has ever been to a truck stop knows its two eggs, two slices of toast and two side orders with a choice of hash, bacon, sausage, or fresh fruit. Although the fresh fruit isn't exactly appealing to anyone that drivers a sixteen wheeler for eighteen hours a day but it is nevertheless an alternative to all the grease. We'd plan out the next few hours of travel distance before we would stop again for lunch. She would take over the driving... and I have never let anyone drive my car but I would let her... so that I could catch a few hours of sleep.

We'd travel like that for days on end until we finally found a small town or a big city that she liked. I had enough money saved up for an apartment and to turn on the essential utilities. Electricity. Heat. Water. Telephone. We wouldn't even discuss the cable issue. We wouldn't need it... at least not right away. Our nights would be well spent. After a long day of work for both of us, we'd come home and read to each other. Stay up all night discussing the literal and underlying meaning of the piece. The author's intentions for the readers. The plot itself. Until one of us fell asleep in the others arms... content... safe... relaxed. God, how could I have messed up so bad?

The least she could have done was give me a second chance. Okay maybe more like third. But I was finally ready to be everything she needed me to be. She would finally be able to count on me. I blame her. If she hadn't kissed me first... who the hell am I trying to kid? If she hadn't kissed me, I sure as hell would have kissed her and I still would be head over heels in love with her. It's a good thing I'm having this conversation with myself. I have a reputation to protect. Reputation? What a fucking joke! Never mind, I don't have a worthy reputation or legacy to protect. Forget? Definitely the only option. Consider my past almost forgotten. Almost.

Damn it! I don't blame her for saying no. I did this all wrong... twice. I told her I loved her... finally... after a year of being out of touch and then I got in my car and drove away. What the fuck kind of romantic gesture is that? I should have stayed. Waited. To see what she would have said. Would she have said it back? Who knows. But what right did I have to come to her after three months and ask her to put her life in my hands. None.

God, how did I become such a loser on the boyfriend scale? That aspect of my persona is completely damaged. Shane. It was her and every other girl before Rory Gilmore. I mean they were simple. Insignificant almost. A distraction. Bur seriously what more did I expect? All that existed in those relationships was the endless groping and make out sessions. I never cared about any of them. Not that I could. They all had the intellectual capacity of an average twelve year old and not a single one of them could tell the difference between Fitzgerald and Hemmingway. And not one of them could hold a candle to Rory.

Finally I pulled into the parking garage a half block away from my apartment in the city. I pulled into my regular spot on the fourth level and turned off the engine. I looked at my car. Examining every scratch. Every dent. The rust. The two toned paint job. I was just so fed up with my life and the direction it was going in. I lifted my leg and just kicked the front, left fender a couple times with my black steel toed boots before walking to the elevator that took me down to the busy streets of the city. You would think that at 3 am on a Friday night the city would be sound in quiet. In Stars Hollow it would be. It'd be calm and quite. The air would be still and cool. God, I missed the quiet nights in Stars Hollow. Thank god that was one of the few things I missed. But New York... it's alive and bustling. Even in the wee morning hours

I walked with my hands buried deep in the pockets of my jeans and was in front of my building in two minutes flat. The plan was to pick up my things... the very few things I owned... and leave. That was my revised plan.

What am I doing? I asked myself one hundred times over. I must be crazy. I mean lock me up and take me to the asylum. I'll admit myself freely. I'll even promise to try and be as entertaining as Halle Berry was in Gothika. I'll even try and get my license to be a therapist before I commit myself. Robert Downey Jr could be my shrink who tries to help me. It will all be great fun. Much better than the movie. Minus the whole creep factor that the director and screenwriter insisted on adding.

What else could possibly explain my reasoning? Insanity. Taking a taxi from New Haven back to Stars Hollow at 3 am. Psychosis. I had to be suffering from some sort of psychotic break.

The entire cab ride I did nothing but think. Think about Jess and what he said and what he meant to me... what he means to me. I want him in my life again. And to go to these lengths to accomplish that feat. I must be neurotic. All I could contemplate was the next step.

On a good day, when my head wasn't all muddled and bemused, I probably would have started a nonchalant conversation with the driver. Not tonight though. Not that he didn't appear to have some interesting tales to tell. Seriously, I've watched the 'Taxi Cab Confessions' on HBO about a hundred times. Okay a bit of exaggeration. Maybe I tuned in more like five times but still I'm sure not of his tales could top picking up three drag queens on 5th Avenue and driving them over to Broadway so they could meet their 'dates' for the evening. Let me mind you their 'dates' were three business tycoon types... definitely lookers... and they were going to see Cats. I will never forget the expression on the cabbies face when he saw the three guys. It was like the Visa Check Card commercials. Tickets to a Broadway show - $120... New Calvin Klein dress for the show - $300... the look on the cabbies face when three well dressed business men picked up 3 drag queens... PRICELESS.

Before I knew it the taxi came to a stop in front of our destination. I handed the driver two twenty dollar bills for his services. "Thanks for the lift," I said as I climbed out of the yellow vehicle. "This can go down as the most uneventful ride you've ever given."

"Not so much. I once picked up a mime for a street festival when I was driving in LA. His hand movements were just annoying. At least I know that you had something on your mind."

"That obvious?" I asked as I crossed my arms across my chest.

"Kid, you're not the first college student I picked up a 3 am to bring to some small time. Trust you won't be my last."

"So was it the deafening silence or the staring out the window blankly?" I asked. I wanted to figure out what it was. I had to be ready with my best poker face to get the information I came for.

"Good luck kid." He responded. He had obviously evaded answering my question.

"Thanks." I responded as I watched the yellow car drive off into the night.

I took a deep breath and turned around to face the building. Somehow it seemed different. I was receiving a completely different vibe. It was impossible. I was just here last weekend. Whatever. I didn't have time to dwell on the feeling.

I walked up to the glass door, and despite the sign that indicated otherwise, Luke's was about to be open for some serious business.

"What the hell?" I could have sworn I was hearing things but I was wrong. Someone was downstairs at the diner banging relentlessly at the door. Calling my name. Lorelai. That was my first thought. But even I knew she was at home getting sleep. She had the test run at the inn tomorrow. Then again she could be up suffering from anxiety. She must want coffee.

I kicked off my blanket and throw my legs over the side of my bed. I sat there for a moment with my head in my hands. I rubbed my hands over my eyes... forcing myself to wake up some more. I stumbled off the bed and felt my bare feet hit the cool hardwood floor. I staggered slowly towards the door and opened it. Before heading downstairs I looked at the clock. 3: 45. God damn it.

I wobbled down the stairs. Hanging desperately onto the railing to hold my footing. The banging continued. "Hold on" I screamed. Secretly I hoped it was Taylor so I could beat the life out of him. I pushed my way through the curtain and made my way to the door.

Imagine my surprise when I finally unlocked the door and found the youngest Gilmore standing at my door step. "Rory," I said acknowledging her presence as I tired to focus my eyes. She stepped right past me, into the diner. She appeared frustrated and out of breath. Something was definitely on her mind. "What are you..."

Before I could finish my question it was answered. "Luke, I really need your help. And you know that I would normally go to my mother about this but she won't understand this. Definitely not this. Considering who it's about. I just really need your help Luke. I didn't know where else to go."

I closed the door and showed her to an empty seat at the counter. I snaked around and turned on the machine. "Coffee?" I ask. It was more than understood that she needed a cup but I had to say something.

"Of course."

I turned around and placed my hands on the counter top to stabilize my balance. I was become more awake every moment. I had to carefully approach the topic. "Rory, exactly what is it you need help with?"

She was struggling to find the words. I could tell. She wanted to ask me the right way. "I need to go to New York."

Immediately I was thrown back. "New York?"

"I have to... I need to..." She was stuttering in the way only a true Gilmore could. Lorelai did it all the time. Every time we fought she would start to stammer over her words. It was a trait that let me know she was annoyed... and nervous. But with Rory... it meant something life altering. I knew it.

"Rory."

"I need to go and see Jess. Tonight."

A/N: Taxi Cab Confessions was an actual series on HBO. I am not aware of an episode that aired as I discribed above... I made it up strictly for entertainment purposes.