Letters Jess has written to Rory over the years. Rated M for language and sexual references. Gilmore Girls isn't mine! Hope you enjoy it!
Dear Rory,
I'm writing to say I'm sorry I...you know. I wanted to stay but it's not a good idea, right? I'm glad you're okay. I'm sorry the car got wrecked. Hope Dean doesn't get mad at you. You know your boyfriend's a complete jerk, right?
Damn. I can't send this now.
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Dear Rory,
Who decided letters should start with dear? It's so Jane Austen. Don't sigh like that. I know she's a good writer, I just can't get behind how formal it all is. You're going to lecture me on how relevant she is, aren't you? Okay Rory, I'll listen if you read Hemingway.
Guess this letter's over. It's not like I can see you to compare.
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Rory,
You came all the way to New York to see me, in your uniform, and spent half the day here. Why? Just because I didn't say goodbye? A long way to come just to say that.
What's my point?
Congratulations to your mom. I hope she likes Belinda.
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Rory,
I'm glad you came to see me. Forget that other letter (which I tore up, but anyway.) I wasn't surprised to see you. Does that sound weird? I never expected you to come but it didn't seem weird to see you, hear your voice over my shoulder. And that smile you had. Damn, Rory. People have it wrong when say you're so good, act like you're so innocent. You come see me in New York, ask me to turn right. I know you're with Dean but I feel like -
Forget it.
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Rory,
I'm coming back to Stars Hollow. I know I hate it there. I know I've talked about how crazy that place is, where you throw a festival for the first snow of the season (though that's just your mom, right?) And I wasn't exactly the most welcome member of the community. I thought I wanted to go back to New York, be able to make three turns and actually be somewhere new, but I - it's not the same. My mom's never home and if she is she's getting excited about her own stuff. Luke always asked how my day was, where I was going. Damn, this isn't what I meant. I want to see you, Rory. I want to make fun of this dumb town together. I want to be with you, I want to -
Never mind.
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Rory,
You kissed me and asked me not to say anything and then Luke tells me you've decided to spend the summer in Washington. You didn't even tell me yourself. You never said goodbye. That's a really shitty thing to do. You came all the way to New York to ask me to say goodbye and you didn't even tell me you had plans to go away. Call me crazy, but maybe Washington was so appealing because it's away from here? And I've always said that about Stars Hollow but you've been the queen of its parades. Literally.
I feel like I'm an idiot coming back here. I haven't received one letter or phonecall from you and no one's going to give me your address. Not that I'd try and call you. Forget it. I'm not going to sit around waiting for you to come home. I'm not my uncle. You know he's totally in love with your mom, right?
I don't know what you think. We both know that.
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Rory,
Screw you.
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Rory,
I didn't mean that. I'm mad at you but I don't mean...I ripped it up after I wrote it, but I didn't mean it. Damn, this writing thing is like a disease. I keep writing letters I'll never send. It's something to do around here, I guess. Luke keeps looking at me with the dumbest expression. He keeps saving the pie I like and acting like it's normal. He asked if I was okay the other night. I can't stand it. I spend most of the time on the bridge reading. It's the only place in this town I can handle. I think about you when I sit there so it's not all good. I'll take it though.
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Rory,
I've hooked up with the girl who works in the beauty store. Her name's Shane. I was walking past and she asked if I had a light. I smoked with her and things moved on pretty quickly. She told me her last name but I don't remember it, and I'm pretty sure that's mutual after telling her mine. We have fun and there's not much of this around here. I just wanted you to know I'm not going to sit around waiting like Dean would have. Not that he's here. Two perks in one week - at least something's going right. What with the run on snowcones last week, there's just too much excitement to take.
Paris ruling Washington yet?
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Rory,
Don't you dare be mad at me. You don't do anything and expect everyone else just to mindread and do what you want. You won't even tell me what you want. I know why you're mad, but the last time I checked, you still had a boyfriend and were going around pretending we never kissed. And if that's the way you want it, I'm certainly not going to hang around hoping you'll wake up. You can go on pretending with Dean and I'll go on hanging out with Shane. We don't talk much, but who needs conversation? Apparently we don't.
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Rory,
I miss you. I miss hanging out with you and talking about books and talking to you and when I fixed the sprinkler and saw you I wanted to -
You get the idea.
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Rory,
I can't believe Dean broke up with you at the dance marathon. Guy's a total jerk. I've said it before but now I really mean it. Who does he think he is? Doing it front of all those people, humiliating you like that - complete jerk. Asshole. You deserved better. You are better. When I saw you on the bridge, your eyes shining, I wanted to make it right. I can't.
So now we're together. Why do I feel so weird?
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Rory,
God, you're so beautiful. Kissing you like that wasn't enough. Holding you to me, breathing you in, feeling your smile - I can't describe it. Anything I try turns out totally sappy. It ached seeing you go. I guess we have each other in the future. I can't stop thinking about you, can't stop this stupid grin on my face. Luke yelled at me, some crap about sneaking around and breaking his rules, but I didn't listen. None it matters. It's just us.
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Rory,
I'm sorry I didn't call. I was working extra shifts to save up for the Distillers and I wanted it to be a surprise. I knew you'd love the concert. I'm sure you did. You held my hand and kissed me and pressed against me, but then you wouldn't look me in the eye when I dropped you home. Is it because of the message on the machine? I was going to delete it but Luke pressed play as soon as I got through the door. He said he couldn't believe you could get mad like that. I can. I'll pretend I didn't hear, it's obvious you're embarrassed. I didn't know you were waiting for me to call. I feel bad now, but I wanted the concert to be a surprise. I don't know how to be a boyfriend.
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Rory,
I never knew Stars Hollow could be fun. Hanging out with you, watching Almost Famous and eating takeout and just laughing - it's too perfect. I like making out on the couch with you and I like just talking and not doing anything. I can't believe I want to come home every day. Take out that bonehead school and everything's perfect. Small towns have something going for them after all.
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Rory,
Are we going to do this? Would you believe me if I said I was nervous? I'm not a virgin. You know that. It wasn't a big deal before, it was just sex. Everyone I was with - we knew what it was. And it wasn't bad, exactly, but it didn't mean anything. This means something. I want it to be good for you. I don't want it to be awkward and weird and have nothing going for it, other than it being safe. I know you don't want anything dumb and cheesy like a record playing and scented candles, but it should be good. Not an after school special. I feel kind of weird writing this, but when we kiss, I don't think of those things. I want to kiss you harder, further, feel your skin on mine. I can't think at all. When we kiss like that I relax, know we'll be okay.
If only I could get over myself and tell you about that stupid swan. Are you ever going to confess to egging my car?
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Rory,
I'm sorry. It's not enough. It wasn't what you think. I can't explain, I can't explain it to myself. I'm such a mess. I'm not right for you, I'm not right for anyone. I'm leaving because I've got to start figuring stuff out and I can't do it here. You have to know I can't stay here. Luke threw me out and even if he didn't, what am I going to do? Stay in Stars Hollow acting like everything is fine and dandy while you go to Yale? I want you to go. I was excited - I am excited - and I planned all the quickest routes. But I can't do it, Rory. I don't know what I'm going to do and if I stay there I'll wind up selling stuff on the street and screwing things up even more. You need to leave and not be with me. I'm holding you back. I'm disappointing you. You just got off the bus and the way you looked when I told you I couldn't get prom tickets - I'm such a jerk. It was the one thing I wanted to do for you. I never wanted to hurt you.
I'll call you. I promise.
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Rory,
So it's over. I knew before you answered. I wanted to say something, but what the hell do I say? Sorry isn't enough. I let you down. I knew it but it hurt to hear you say it. You're not going to pine - isn't that what I said when you went to Washington? Part of me wants you to miss me. I'm a jerk. I'm sorry. I'm sorry about not telling you things and yelling and leaving without telling you. I'm sorry we can't go back.
You may have loved me. God, Rory. I can't even write the words. I wish I was more for you. I've hung up the phone and I won't call again. I'll leave you to live your life and try starting mine.
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Rory,
It's hot and the beach is beautiful and all I can think of is how you'd squeak at the sand between your toes and try and push me in the water. There's so many bookstores I want to show you. We'd stay until they kicked us out. I've got a book I was going to lend you, the margins half done. How many books did you have left to bribe me with?
I don't want to think about missing you. How's Europe? It's weird living with my dad but we're having conversations. That's something right?
God, I miss you.
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Rory,
I wasn't going to say anything. I wasn't even going to see you. I was just going to get my car and leave. It's not my fault it was a piece of junk and broke on the road and Luke reclaimed it. It's not my fault we wound up going to all the same places. The only decent parts of town. I wanted to talk to you, but it wasn't the right moment. And then the moment just happened.
I love you. I loved you when I called and you said it and I was too scared to. I loved you when we'd just sit together and I'd see how the sun played on your hair. I don't know when it began, Rory, but I love you. And I'm sorry. And I couldn't handle the thought of you saying you didn't love me anymore so I left. I messed up. Again. But I had to say it.
You look different. It's not just that you cut off your hair. You look different, Rory. Do I look different to you?
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Rory,
I miss you. It's cold and I can't sleep and I miss you.
That's all
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Rory,
I can't believe what happened. The words are crashing in my brain and the look in your eyes. You don't want to be with me. You don't love me - do you? I don't want to know. Everything's fallen apart.
It's such a fucking mess. You know, I started to think maybe stuff was changing. I made peace with my dad and his crazy family, I got a place in New York. It sucks but it's a place. We started getting along, my dad and I, but I couldn't stay there. I had to go back to New York. And then Luke came over and yelled all this stuff about Liz and how I was missing something good for her (he obviously didn't go to any of her other weddings) and that I owe him. I went for him. It wasn't just that I'd get a decent meal and an actual bed - I wanted to make him happy. I feel like such a jerk, Rory. And then he gave me this self-help book and it sounds like something out of Bette Middler's mouth, but there was some pretty good advice. And I think Luke and I are actually okay again. So I knew I had to talk to you and make things right. I was an ass, wanting you to call. I knew you couldn't but I told myself you could if you wanted. I was too scared to - anyway, I was going to say all this. Tell you I cracked and got a cellphone so you can call, if you want to. Say I was sorry and not just for that and maybe we could figure things out again. I was never going to ask you to run away with me. I just freaked out, when I saw Dean, and started saying all this stuff without thinking. I don't want you to leave school. I want to you stay graduate and do all the amazing things you had planned. I still don't know what I'm going to do but I wanted you to know I'm trying.
I didn't say any of that. And now you never want to see me again and I lost any chance with you. I can't change anything.
What was Dean even doing there? Isn't he married? It all seemed weird, now I think about it.
There's no point in writing any of this. I might not ever - I don't want to put that down. I want to forget about this. I'm going to try writing something else. I don't know what yet but I'll find out.
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Rory,
What the hell is going on? I haven't seen you for two years and you're living with your grandmother and dating this jerk? Not talking to your mom? Dropping out of Yale? What the hell? You are screwing up, take this from someone who knows. I know you. I know this isn't you. I don't know what's going on but you need to get back to school and dump this guy. I'm guessing things are serious between you but I don't understand. He's a jerk. He took one look at me, at us, and spent the whole night trying to start a fight. Yeah, I can talk, but I'm not eighteen anymore. Aren't we supposed to have grown up, in theory at least? I still can't wrap my head around this. I'm in a good place for the first time and you - I don't know what's happened but it's bad. I know you miss your mom, too. I always teased you for being so close, but she's your best friend. Don't throw that away. You look sad, Rory. Your smile is sad. When was the last time you laughed?
Rory, you can figure this out. It's hard but you can do it. I'm here if you want me to be. I don't think you do, but for what it's worth.
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Rory,
So that's it. I don't know what to say. You came here, smiling, looking happier than when I saw you last, and told me everything was fixed. I was happy. I was happy for you and for me and this thing I have going here and thought, for the first time, we'd both got our lives together and were doing decently. I loved showing you around. I loved seeing you again. I loved talking to you, smiling at you and - I didn't plan on kissing you. Not when you showed up. But when we sat together and you looked at me that way, it felt right. And you kissed me back and for a second, it was perfect. Thinking without thinking. Does that make any sense? It was just us. And then you were pulling away and talking about that jerk and how you couldn't cheat on me and how he cheated on you. He cheated on you and you're still with him? It's like we're at the bridge all over again. You deserve better than that. I knew he was a jerk. But me saying it won't do anything. You'll figure things out, Rory. I did. I couldn't have written my book without you telling me I could do more. I hope you know you can do more too.
What is it with us? It's been years since we met and now it's like we're back where we started - you kissing me and pulling back, saying it can't mean anything. But it does. I know and you know it. You surprise me and you don't. When I saw you walk in, all I thought was, of course. You're here at the strangest moments but they always make sense. And it's never the right time. It is what it is, you, me. Maybe one day it'll be right. It's never the last conversation with us. I'm angry with you but not very. I always want to listen. I always want to see you. Maybe when it's easier, we'll find each other again. Whenever I go to New York I sit on our bench, hoping you'll find me like you did that day. As for now, I'll do what I do with every letter to you - tear this up.
Rory. You're the changing constant in my life.
Love,
Jess