Title: Figure It Out On The Way

Summary: Rory and Jess. Analyzing. Over-thinking. Trying to learn to love each other. And knowing that you have to start somewhere.

A/N: Set sometime after Sookie's wedding, but well before the dance marathon. I've got a couple (short) chapters ahead already written, but I'm missing a bridge between this one and part III... so until I can figure that out, feedback is definitely appreciated!

I. The Feeling Is Familiar

In my experience, things never really go the way I plan for them to. I think I've learned to expect that. I know I can't control the way the cards fall, so sometimes I put forth some kind of effort and sometimes I don't bother. Either way, I try not to worry about it too much. I know I can't count on stability, or routine, or getting what I want- but I can count on me. I know who I am and I know how I feel about things. I know what's possible for me and I know what's not worth my time. I don't know where I'm going. I figure, as soon as I pick a place, it'll immediately be taken out of the running for me. It's less disappointing to just not go after things at all, for the most part. To just roll with punches.

Liz happened. Robbie and Jake and getting busted and a night in jail happened. Stars Hollow happened. Rory Gilmore happened.

Rory Gilmore. And suddenly all the things I thought that I knew about myself started to crumble a little bit. Started to fray at the edges.

She made me want things I shouldn't have wanted. She made me feel things I wasn't expecting to feel. Made me go after those things. Things that I never really had much chance of getting in the first place.

She confused the hell out of me. I'm not used to feeling uncertain. I'm not used to wanting things I can't have- I'm usually smarter than that. I'm not used to worrying about what someone else thinks of me. I'm not used to trying to impress someone.

I'm not used to caring like that.

But Stars Hollow happened, and Rory Gilmore sure as hell happened, and I guess I just did my damnest to keep my head above water and deal with all the unfamiliar feelings.

And eventually things started happening. We moved forward. It wasn't always exactly how I pictured it happening; it wasn't always easy. But I thought we were getting closer to some semblance of a happy ending. Or if not a happy ending, at least a valiant attempt at a good start.

Somehow, unreal as it seemed, things appeared to be going in my direction.

Well, more or less my direction. I made her laugh. I held her interest. I think I made her sense on some level that there was so much more out there than her small town life- things that would excite her, things that might scare her, but above all else things that would make her feel alive.

And then I crashed her car. I left her, and I left any ideas I had of making plans and finally, finally, getting what I wanted.

But she sought me out. So I bought her lunch, I took her to a record store, and then I followed her back to Stars Hollow.

And she kissed me. And welcomed me home. And made me hope. Made me think I had a shot in hell at love with her.

But she's always been easily frightened. She's always been a runner, whether literally or just in her head. She's never been great with going after the things she really wants, as much as she keeps up this pretense of being ambitious. And as soon as the things she truly wants can't be guaranteed- forget it. She'd rather stay cocooned in what's safe and stable and right there in front of her, than chase after something that could be so fucking amazing- but could also turn out to be nothing.

Rory Gilmore may have wanted me, but she was never strong enough to do anything about that.

And in my mind that's always translated to something more along the lines of: She didn't have enough faith in me for it to be worth it. I was never really good enough for her.

Maybe all of our shortcomings can be explained by the way we grew up and the insecurities we carry with us. Maybe her father never being in her life has made her unconsciously seek the kind of normal, ordinary stability she missed out on as a child. Maybe growing up with a mom who could never really care for her son left me forever doubting my self-worth; doubting that anyone could ever see anything worth loving in me.

Regardless of the reasons or the psychoanalytical breakdown, somewhere along the path of our twisted relationship- if you could really even call it that- confusion turned to anger.

She did what Rory Gilmore does- she ran. She left. Without a word. For three months. And when she came back, she was still with him. Still living her fairy tale fucking life, without a single shred of concern for what she might be doing to me.

Because people like me obviously don't factor into lives like hers. And I knew that. I really did. But somehow, at some point, she had me banking on impossibilities.

God damn her. For making me hope. For making me want to love again, after so many fucking failures.

Jess Mariano, hope, and love. Things that don't go together.

And so this, at least, is a feeling that I'm familiar with. I remember angry. I know how to deal with angry. I know what angry means and where it usually takes me. The sadness that's mixed in, well, that's not as familiar... but I'm doing my best to block that part out and focus on just the anger.

It's not what I want. But I try to keep reminding myself not to want things I can't have anyway. I used to be good at that. I'm sure I can relearn that skill. Learn how to bank of the few things I can count on again.

So fuck Rory Gilmore. If she's ready for something more, she can go ahead and go after it and see what happens, no guarantees. And if she wants to stick with the fairy tale and never step out into the unknown, then that's her fucking choice.