Straight from your heart.

I wrote my first "I love you" letter when I was 18. It wasn't my first "I have intense unending adoration for you and all you do", that was at 14, and again at 17. The first LOVE YOU IN THE WAY THAT I WANT TO KISS YOU ON THE MOUTH letter waited until winter of my freshman year of college. I hand wrote it with skinny Crayola markers, skipping every other line in case my handwriting was horrific (it was), and gave it to the object of my affection at a dinner party that I hadn't been invited to but crashed anyway. She slipped it into her bag and waited for her mom to come pick her up after we'd all disbanded for the evening.


Even though my raging crush has passed, we're still great friends to this day, and my life would be so much more boring without her in it!

The second love letter I wrote was to a friend of mine who I'd been hopelessly devoted to for the entirety of my adolescence. He was my date to Senior prom (obviously all of this occurred before I realized I was HELLA gay) and we'd been through a lot together. I wrote him an email, held my breath for three months, and finally heard back from him.

"This is really sweet of you, I'm glad I got this, because I don't usually check this email anymore!"

We proceeded to hang out on Christmas break, as we normally did, and had a really intense four hour not-date, where he let me down easy and explained his situation. Life was crazy, and he hadn't been single since he was thirteen. He needed a little time to adjust to being a person who didn't have to acquiesce to the wants and needs of another person.


We haven't seen each other in a hot minute, but I still consider him a great friend.

The third I love you letter, I sent today. I don't have crushes often, hardly ever—actually. I decided to try this one out. This girl and I have a lot of weird common idiosyncrasies, and she's beyond attractive. I'd been trying to go about things in a very rib-nudgy way. Like, "Hey hey hey, you're pretty cute. You wanna do a thing that we both like together? Maybe we can get fake twitter married or something...?"

Finally I remembered that no one is a mindreader and straight up sent her a message that read something like: YOU'RE SUPER COOL. I REALLY HOPE YOU'RE GAY BECAUSE I LIKE YOU IN A STUPID MIDDLE-SCHOOLY SENSE.

I wasn't even really expecting to hear anything from her, I just needed to send her a note so I could get all of the crush-feels off my chest.

She wrote me back today and sent me THE nicest note ever. It effectively was like, "I'm not gay, but I think you're really cool too!" ...annnd then I blushed a lot. It was awesome!


What's cool is that she was the first friend I made on tumblr. We've e-known each other for almost half a decade!

In any case, I know word vomiting all of the feels you have into a letter and delivering said letter to its intended target isn't for everyone. I have to work up a lot of courage before I even figure out what I want to write, let alone before I send it out into the universe!

Here's what I would suggest if you want to write someone a crush letter: 

1. Don't worry about whether or not you want to send it. A lot of times, I'll end up writing twenty drafts of crush letters before I decide which one I'm going to send out. Some of them just help me expel my feelings, some of them provide useful excerpts that I'd like to throw into the final draft. Even if you don't ever feel like you'd want to send your crush letter, it feels good to just have one sometimes. Or just to know that you've gotten those feelings out of your system. If you decide to send it, great! If you decide to keep it in your journal and not let anyone ever read it, great!

2. Be concise, but be yourself. The first letter I wrote was really wordy. The girl I sent it to wasn't super dense, but I definitely had to explain it to her much much later that I'd actually written her a letter that essentially said: HOLY FUCKING CRAP I HAVE A HUGE-ASS LESBIAN CRUSH ON YOU. That was a fun conversation...heh. In any case, this is why going through a few drafts of something is helpful. You can cut the fat, and get rid of all the stuff that doesn't say *exactly* what you intend to say. Maybe you wouldn't write a letter that says something like: I WANT TO DO A SEX ON YOU IMMEDIATELY. The last letter I wrote said something to the effect of: I want to make us Chemexed dark roast and listen to jazz radio on Saturday afternoons with you. Sure it sounds super cheese-tastic, but that's exactly how I feel about this girl. That would be a thing I'd really want to do with her at some point. How do you feel about the recipient of your letter? What is it about them that makes your world a little brighter? How can you say this in the way that's the most efficient, and the most YOU?

3. Realize that you're writing a crush letter more for you, than for your crush. The sad thing about love, (or crush) is that no one owes you shit at the end of the day. You have to go into it with the realization that a few things might happen:

  • You may get let down gently (as I always have been) and politely set free to go fishing for a different equally wonderful human being.
  • You may get crushed (as has sometimes happened even when I've been let down gently) but with this, you now have knowledge that you didn't have before; which allows you to pick up and move on.
  • You may hear nothing. If your intended crush recipient is someone like Taylor Swift, maybe you should ready yourself not to hear back from her. The person who you wrote your letter to may not want to write you back. It's agonizing, yes—but it's their prerogative. Don't go postal on them if they don't write you back right away. They may not know what to say, or how to say what they want to say.
  • You may get a letter back that reads something like this: "I've felt the same way about you for so long but didn't know how to bring it up!" Essentially, you then become the hero for cutting through all of the awkwardness and the two of y'all can start planning a wedding. Make sure to invite me!

Writing a crush letter can be really scary, but if you're like me I always feel a LOT better after everything's said and done. Hopefully it'll make you feel as good as it makes me feel! (Though I suppose relieved is more the word I'm looking for.)

Happy expressing yourself~!