Freelance, Letters

A Letter of Obstacles

Dear _____,

We’re not together anymore, I know that. I’m aware. And I’m just confused because I still have really strong feelings for you. Or at least I think I do. There’s times where I think about you, or when I just experience life with you where I feel so happy and beautiful. You don’t have to do or say anything, it’s just the small things you do that make me feel good.

Since we broke up, it’s felt like without the titles and expectations, I’ve been able to just breathe and enjoy you for who you are and just how great we are together when we’re intimate. I know we can’t just keep breaking up and getting back together which is why we kinda just left it at that. Or maybe I’m just assuming things again. I don’t actually know how you feel about any of this anymore, I thought we were on the same page, but I’m always on a completely different page from you.

Just in the past few weeks alone, it felt like things were getting better for us. I’ve told you this before, since we broke up it never felt like I lost you, I still feel like I have you by my side, I still have these feelings for you. Or maybe they’re not even feelings. Maybe I’d just rather be with someone than be alone.

Pros Cons
  • An amazing kisser – to the point where my heart melts and simultaneously, chills spread through my entire body.
  • The way you suck on my tits – holy fuck, it feels amazing and you’re so good at it.
  • The way you take control when I suck your dick, and I honestly love sucking your dick. It’s probably the only time I’ve ever enjoyed it this much, and even swallowing your cum, something I’ve never done for anyone else.
  • The way you lift my leg up when we’re making out against a wall, just turns me on.
  • The way you fuck me – I can close my eyes and recount almost all the times you’ve fucked me and just imagining it alone gets me turned on. I get wet just thinking about you
  • The way you turn me on in general.
  • Handsome. As. Fuck. – really attractive; your smile, your jawline, your eyes, ugh. Really hard to stay mad at a face like that in all honesty.
  • The fact that we’re not together, so you’re not obligated to do anything for me anymore, but it’s that much more meaningful when you do
  • You make/made time for me – even though we’ve broken up and we’re not together anymore and we’re just friends, you’ve managed to watch movies with me on the phone, have video calls with me, talk to me late at night.
  • You’re funny. I value good humour.
  • When we were together; you’d do things for me you wouldn’t do for anyone else.
  • You’re really smart. I’ve learned more with you than I could have ever learned myself, so thank you for that.
  • You’re my plug. For everything. Good tv shows, movies, culture, memes, I’d live in a rock without you.
  • The way you look at me; whether it’s a dirty look, or a look of endearment – though I can’t stare back for long without blushing I like it
  • Even though we’re not together anymore I still think about you all the time. And no I don’t expect you to do that in return. – Thinking about you is what gets me through my days. Especially at the bank – I can just think of the 100 funny moments we’ve had together and keep up a genuine smile towards others.
  • That you share things with me sometimes
  • That you’ll initiate plans sometimes and it’s really sweet, like asking me out to dinner, or a movie.
  • You don’t care. This is a huge con in itself, it’s almost as if this con alone is the root cause of every other con.
  • You can be really inconsiderate.
  • You seem like you have feelings but can just sometimes be so cold and it confuses me. How can you have all these pros and then just not care? It’s so confusing. I get dizzy trying to wrap my head around it.
  • That you don’t trust me. – It’s not your fault, but I can’t really see us working out if you don’t trust me. – Then again we’re not working out; we’ve already broken up, right?
  • When I try to be more vocal and honest with you, which is something you’ve said you wanted from me – you spit it back in my face and call me over dramatic.
  • You’re selfish. It makes me wonder if any of the gestures I think you do to for me were for me at all.
  • I don’t trust you. Mostly because you can make me feel amazing with things you say or the small things you do, but can turn around and just suddenly not care, or be cold towards me, or just not give me any sort of action that shows that you mean what you say.
  • You don’t know how to apologize. Not even for the betterment of a relationship with someone, even if we are just friends, if you’ve hurt my feelings in someway, and if you cared about your friends (which it’s obvious you don’t) you’d apologize for hurting them, whether you meant to or not.
  • You think I project myself onto you. I don’t. I’m not thinking about me. I’m trying to think of who I think you are and it never matches up. Guess I don’t really know you if all I do is guess.
  • Nothing excites you.

Score 17:10. I just needed to put it in writing, this letter isn’t really for you. I wanted to know if the pros outweighed the cons. And they do, but not by much, because I haven’t even listed all the pros. I don’t need to. And they do outweigh the cons in list form, but I do value someone caring, considerate, and someone that trusts me and for me to trust them in return. You obviously don’t think I mean anything I say, and you think that I project myself onto you. I want to trust you. And I feel that 80% of the time I do believe everything you say. In terms of facts you share with me, feelings you have when you express them, there’s small things I don’t believe you for, an example would be your body language towards me asking you to go downtown with versus what you were saying in words. Body language speaks for itself. It doesn’t lie. And I know that nothing excites you but if that’s the case, then why say “you’re down” when you’re clearly not. If all you wanted was for me to give you some head and send you home. I would’ve done it.

Cause I know the only reason we’re even fucking is to “entertain your own selfish needs” and I willingly accepted that. I didn’t expect you to say that you did want to go downtown with me, we’re not dating anymore, you’re not obligated to do anything for me anymore. Which is why when you genuinely (or when I feel like it’s genuine I guess cause I just don’t know anymore, I can’t assume) spend time with me, it feels that much more special because you didn’t have to. You didn’t have to video call me, you didn’t have to watch a movie with me, you didn’t have to grab dinner with me, you don’t have to do anything for me or with me anymore. But you do. And it makes me feel really good when you do. I’ll admit it. I like it. I really like that I’m important to you, because you’re just as important to me. It feels good to have that feeling returned. But for the most part I feel that the feelings I have for you, and the things I’d do for you are merely unrequited. And again I don’t expect those feelings to be returned. We’re not together anymore. But the feelings I have haven’t changed.

Maybe I need to let you go altogether. Truly just get over you, like you seem to have with me. I’m way too weak for you. I willingly put my self in a position to get hurt with you, just to have sex with you. I’m a fool. I can’t resist you, I’ve tried. I’d rather be hurt by you and still be with you, than not have you at all. And the hurt isn’t that bad. It doesn’t hurt that much, I’m honestly happy for the most part, but I do feel hurt at times when I think about the fact that we’re not together but all the feelings still remain. I don’t cry. But I just feel a little sad when I think about it. And I think about not talking to you anymore, and I just want to not talk to you altogether. I wish I didn’t need you. I wish I didn’t want you. I try to do things to stop thinking about you. But even being on Instagram, I’ll see a post of Mad Max and just think of you immediately. And I want to share things with you, funny posts that I see that I feel like we’d laugh at together, art, music. I want to share with you all the time, I love sharing things with you. Which makes it that much harder to stop talking to you. Because I’ll try sharing these things with someone else, and it just doesn’t have the same effect or feeling that I get when I share them with you.

I don’t get the same happiness talking to other people that I do when I talk to you. Nothing is more satisfying than seeing a notification on my phone from you. Whether it’s a YouTube link, or a WhatsApp message. I’m fucking pathetically head over heels for you. So, I think for my own self-respect and dignity, if I have any left. I should just stop. Because if I don’t stop know, that little hurt will turn into more, and it’ll only make me hate myself more. If I want to start loving myself, I should start respecting myself as well. And that means not succumbing into your selfish needs, and being more selfish to my own.

I wish I didn’t have to let you go, and I wish we were still together, but you can’t always get what you want. And neither can I.





Love always,



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