Rory discovers an old, unfinished letter as she sorts through her stuff before heading out on the campaign trail. Having broken up with Logan, there is nothing to stop her from finally finishing it. Set after the end of the show.

The characters aren't mine; they belong to Amy Sherman-Palladino.

The Key is in the Timing

Rory hadn't expected going through her old things to be this hard. She had been away to Yale, to her grandparents' house and yet still, still, this house and this town and these memories had a hold on her that she was sure she would never really understand. Some of her stuff had been moved when the house was redone but thankfully, and possibly due more to Luke than to her mother, the boxes were neat and intuitively labeled.

She was surprised by how much stuff she had managed to collect over the years. She still had some mementos from her time with Dean in here (her box of cornstarch – the first, but sadly not the last, thing she had stolen). Even if things hadn't ended particularly well between them, the first time she fell in love and the boy she fell in love with would always have a place in her heart. It was as she was looking through this box (previously her Dean box but now labeled 'Personal' – another indicator of Luke's involvement as he, though he would never admit it of course, had never really warmed to Dean) that she stumbled across an old pad of paper, still partially filled with blank sheets. Why she hadn't used all the paper and how it could possibly be classed as 'personal', Rory didn't know. She it tossed away but, as sport had never been her strong point, instead of landing on the 'useful' pile on her bed, it slid back to the floor with the air lifting the cover as it did so.

Rory froze in shock. There were only two words on the first page. Two four-letter words which her brain didn't seem to understand.

Dear Jess,

That was it. Nothing else. Nothing offensive or shocking or particularly exciting… just 'Dear Jess'. This was the pad she had taken with her to DC that summer. And that had been the summer that she's realised she didn't love Dean anymore just as this was the summer she had realised she didn't love Logan anymore, or at least she couldn't be with Logan anymore. The parallels were striking. She wondered how Jess was; she hadn't spoken to him since their meeting, their kiss, at Truncheon. Was he mad? Sad? Great, now she was rhyming… The more she thought about it, the more desperate Rory became to finish the letter, one that she should have finished that summer before senior year but hadn't had the guts to. She wanted to believe she had the guts now.

Dear Jess,

Hi. I know this really out of the blue and for that I'm sorry. I just… Jess, this is the letter I wrote to you the summer after I kissed you (well, I didn't write all of it then, just the 'Dear Jess' – for someone who says she's good with words, this letter sure did stump me). I just stumbled across it as I was packing up my things (I've got a job on Obama's campaign trail). I don't know why I didn't throw it out after we got together. I just forgot I guess.

Anyway, I found the letter and I couldn't stop thinking about it and how I'd never finished it and how if I had finished it I might not have had to live through the painful Shane experience. I also couldn't stop thinking about parallels I'd noticed between my situation now and the situation then.

I've broken up with Logan, Jess. He proposed to me but I couldn't say yes. Don't take this the wrong way: I'm not going to confess my love or anything and I'm not writing this to get you as my rebound; I'm just telling you what happened because I couldn't help but notice the recurring theme. Last time, I kissed you and went back to Dean. This time, I kissed you and went back to Logan. Both times, the relationships I went back to ended.

You're a recurring theme in my life, Jess. I wouldn't have this job or a degree without you and your re-occurring. So when I saw the letter, pathetic and unfinished, I knew you deserved better. You deserved a full letter with a beginning, middle and end. Maybe I'm the last person you want to hear from right now and I wouldn't blame you if I were. I just thought you deserved your letter – one with the truth.

And I miss you, Jess. I probably shouldn't have written that but I'm not going to take it back now. You're getting the truth, mister.

I'll include my address in case you want it. I hope you want it.

Rory

A/N: Most of my ideas come to me as one shots but with this story I'm not sure whether to end it here or continue on with letters exchanged between Rory and Jess as she travels round the country – any thoughts or opinions would be much appreciated. Thanks.