A/N: Why yes, I do feel the need to work every possible Season 5 scenario into a Rory/Jess reunion ;)
Disclaimer: All recognisable characters belong to Amy Sherman-Palladino and other folks that aren't me.
Jess was used to junk mail. He didn't really get anything else, except the usual bills and final demands. Nobody really knew where he lived from one month to the next, except for Lily - she was the only person to write him letters. Even then he got them few and for between. This was why Jess paid so much attention when a pretty hand-written envelope showed up in his mailbox. It had so many post marks on it and at least three different people had written on the envelope, including his mother. More signifincatly, the original direction was clearly written by Rory.
Jess didn't know whether to be thrilled or panicked and chose to be neither until he knew what the letter was about. Shoving the letter in his back pocket, he headed out to a spot he knew well, his favourite bench in the local park. His mind filled with thoughts unbidden, memories both sweet and painful that he wouldn't part with for the world, and all starring a certain Miss Gilmore. Jess sat down, took out the letter, carefully opening the envelope ad prising out the pages within. He knew Rory's handwriting so well, and swore the paper even smelled of her - clean and pretty, just like always. There was an odd smile on his lips that Jess wasn't even aware of as he sat back on the bench and began to read. His expression and mood would take a great many twists and turns as he took in the entirety of what Rory had to say.
I know you'll probably be surprised to get this letter. I'm surprised to be writing it also, but there are some things I just really need to tell you. It's past midnight on a week night, and I'm back in my room at home, scribbling away by torchlight even though I'm the only one home. I wonder if you're picturing me right now, like I'm picturing you, maybe on the bench I found you on in Washington Square Park. It's weird to think that I don't even know where you live anymore, hence why I'm sending this letter via everybody else. I only hope it reaches you eventually.
So, my Dad's father died last night, or the night before. My days get messed up when it's this late at night. Anyway, he died and it got me thinking. I never knew him. I met him once but that was all. This man was my grandfather and now he's gone without us ever really knowing each other. That's so scary and strange, and wrong when I think about it.
Me and my Dad have been fighting lately. It was as much my fault as his, I knew that anyway, but when I found out his father died, I just couldn't take it. I barely even remember what we were fighting about anymore. Well, that's not entirely true, but it seemed to get all blown out of proportion and context over time. It can't have been worth it, it just can't.
I love my parents so much, and my grandparents too. Even though none of them are exactly old, that's not the only reason people die. It happens all the time. Accidents, diseases, even murders. It's scary to think of all the things that might not get said or done. I really hope everyone close to me knows how much I love them. If anything happens to me or to them, I need them to know.
I guess you're wondering now what any of this has do with you. Well, you know us Gilmores, why get to the point when we can dance around it in our very own, practically patented, off-on-a-tangent way, right?
Jess, I don't want to leave this world knowing there are things I should've said and done but didn't. I don't want anyone I care about being taken from me not knowing how much they matter to me.
I care about you, Jess. Despite what you might think right now, I love you. I always loved you, I think, from that first day when you walked into my room and asked if we could bail out of the window and escape! You were right about me knowing, just the same as you did, that we were destined. It never made sense. We never made sense, not to my Mom, or the town, or even to me sometimes, but I was happy when we were together, and I did love you. I'm pretty sure I'm always going to.
When you asked me to leave Stars Hollow with you, I didn't say no to be cruel. You know that's not me, don't you? The truth is, I had to be harsh, because if I gave you the chance to try and convince me, I probably would've let you. I couldn't leave, Jess. Maybe if you'd wanted to stay, we could've worked something out, but running was never an option for me.
You told me I could do anything I wanted, and I do believe that, but as brave as I can be, as adventurous as I plan to be in my future, my present is in Stars Hollow and at Yale. It's what I need right now.
Believe me if I could have both, my education and my life as well as you, I'd say yes in a heartbeat, because I so regret what happened with us, Jess. You loved me and I loved you, in spite of our differences, or what anybody else thought. I know it's too late now, but I figured if I could just explain things to you, it'd be one less regret when either of our time comes.
What's that line that Elizabeth says after Darcy finds out about Lydia eloping with Wickham? 'I can't bear to think that he is alive in the world and thinking ill of me'. I hate knowing you're out there thinking I don't care, or that you shouldn't care about me anymore. I want you to know that you will always be in my heart, Jess. Always.
Jess barely finished reading, only seeing Rory's sign off as a blur, as he realised what was affecting his vision. Guys like him didn't cry, at least not where anyone could see, but she had moved him so much with her words. Rory was a writer, no doubt about that, but it was less her skills as a wordsmith and more the fact she had poured her heart and soul onto paper that got to him.
Rory loved Jess, always and forever. It'd sound sappy and dumb if he could get past the part where he was thrilled beyond compare by the revelation. She had said she thought she loved him once, years ago when they were still kids, and he had been so stupid as to run out on her. Now the truth lay before an adult Jess, bright and shining. Rory loved him, and only hope he didn't hate her for all that had gone before. As if he ever could.
Jess folded up the letter and shoved it back into his pocket. He dragged his sleeve across his watery eyes, then checked his watch. He needed to pack a bag, find a schedule for the buses out of here...
The minutes felt like hours as he scrambled to be ready. Then he sat waiting impatiently on the bus back to the only place he ever dared to call home. The journey seemed to take forever and Jess couldn't even bear to read he was so on edge. His legs jiggled so much with pent up energy that they ached like he'd run a marathon by the time he arrived in town.
Jess was a ball of pure nervous energy waiting on the Gilmores' porch, and almost completely collapsed in on himself when finally Rory opened the door.
"Jess? What are you doing here?"
"Having no regrets," he told her, a moment before they fell into each others arms, all happy tears and desperate kisses.
No regrets. Not anymore.