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Hello Jess!
It’s me Rory, in case you didn’t… read the name on the envelope?
Oh wait. Damn it. Let me start over, I did it all wrong!
Dear Jess
Hi!
Yes I know I could’ve just crossed out the stuff from when I said “Hello Jess” but I thought you might enjoy reading some Gilmore Girl crazy.
So I just… well not just, but I graduated from Yale! God knows how though… how I ever actually compensated for that semester I wasn’t here I will never understand.
I can’t believe I’m about to say this, but I kinda miss Paris. She was… a nice reminder you know? Even if I wasn’t Stars Hollow Rory anymore, I had a constant reminder of myself from before Yale whenever I looked at her.
I’m covering the Obama Campaign! How about that right? It pays next to shit but I like it. I start very soon. Too soon. In six hours, I’m getting on a bus and leaving, which is why you don’t have a return address on this letter, I don’t know where I’ll be.
I hope the campaign goes through Philly, I want… I want to see you again.
I hope you don’t hate me, my Jack Kerouac. I hope you don’t mind the nickname I’ve given you. I hope… I hope you don’t mind that I call James Dean too. I hope you don’t mind me saying that I miss your wild hair and leather jacket. I guess I hope for too many things, many things I have no right to hope for anyway.
I’m tying up loose ends. I’m trying… I don’t want any regrets haunting me this time. The last time my life changed, when I went to Yale, I had so many regrets. Too many. Some were not regrets perhaps, they were things left unsaid. This time, as my life goes into its next stage, I’m making sure that does not happen again.
I’m sorry. For what I did. It isn’t what it is. No. I will not accept that. This is too unfair. I was unfair to you and I feel like I still am.
If I could change one thing about that encounter, I would never stop kissing you. Or perhaps even if I did, I would… I would turn right! Like you did. I would turn right and come back to you.
My dearest Jess, I am so sorry for how I've been treated over the years. I know it’s long gone and that magic’s not here anymore. But… I just feel so ashamed.
I hate that our first kiss was me cheating on Dean.
I hate that I never wrote to you when I was in Washington even though I wanted to.
I hate that I refused to accept that I like you and put you and Dean (and probably Shane, I don’t know if she even told you about our encounters) through so much pain.
I hate that I let my mom’s dislike towards you dictate my actions towards our friendship, a friendship that clearly was more than just friendship to both of us.
I hate that I liked from afar and never did anything about it.
I hate that I wasn’t the one who ended my relationship with Dean for you.
I hate that I kept comparing you to him.
I hate that I used the silent treatment as a weapon against you.
I hate that I didn’t believe you when you said you didn’t get into a fight when you had that black eye.
I hate that when you told me you loved me I didn’t try to stop from leaving.
I hate that my response to you begging me to run away with you was sleeping with Dean. (Yeah that happened, oh god, I’ve never felt more shame in my life)
I hate that I couldn’t deal with a bad internship experience and my response was to commit a felony and drop out of Yale (this one has nothing to do with you but I guess it still irks me)
I hate that I didn’t break up with Logan when you came to see me, when I clearly wanted to do it.
I hate that I didn’t break up with him after he slept with his sister’s bridal party.
I hate that I came to Philadelphia and kissed you only to walk away.
I hate that I let myself forgive him.
I hate that… I hate that I tried to use you.
I hate that I missed you.
I hate that I missed your touch.
I hate that I still miss you.
But…
I hate that you dated Shane to piss me off.
I hate that you never let me in.
I hate that you lied to me about your black eye. (Yes, I know about the swan)
I hate that you left me the way you did.
I hate that you didn’t say goodbye, again.
I hate that I loved you despite all of it.
I hate that you told me you loved me and then ran away.
I hate that you asked me to run away with you when you knew how much I loved Yale, I couldn’t just leave! What were you thinking?!
I hate that you said Happy birthday and left again… why didn’t you stay?
I hate that you said “It is what it is, You, Me.” Those words have been haunting me for so long!
I hate that… I hate that I haven’t heard from you in so long, which was to be expected honestly! I just hate it.
Anyway… I just… you’re the biggest regret of all. Things could’ve been so different!
We could’ve stayed together!
Or maybe got back together again!
Or ran away together (it’s a possibility, no matter how remote or stupid.)
So… so if you could just call me, or just… ask me out again… because I really want to be your girlfriend again. Because at the end of the day, you set my heart on fire, each nerve of my body is ablaze everytime you touch them.
My sad tortured writer, please… one more chance is all I ask from you.
I’ll leave my number at the end of this letter.
But I need you to know Jess, you’re my only one, and no matter what, no matter what happens, whether you call me or not, whether or not you even acknowledge this letter, I am so so immensely proud of you.
You did it Jess, you found your passion and you got successful, all by yourself. You… you are far more than I deserve. You are… you’re amazing. You got exactly where I thought you would get someday. You got big! I’m so proud of you.
We’ll see each other again one day (you know since my mom and Luke are really serious this time), but I hope it’s sooner rather than later.
Yours faithfully and forever,
Rory