If you really want to impress someone, if you really want them to know you love them, that their soul makes your soul a big gigantic pudding, then you really only have one option: You have to write them a love letter.

Honestly. You can get away with just one really good love letter and forget all the other trinkets. Just make sure it is good.

To help you on your Match Quest, I’ve put together the 6 Rules of a Perfect Love Letter as I see them. Trust me: I have been doing this for years. Ever since the Internet first sang its sweet, robotic melodies into my Grade 9 ears, I was reaching out, writing insane, terribly human and terribly soulful love letters. And I’ve gotten pretty good at it.

Forget about buying perfumed papers, or fancy pens and all that sparkly garbage. This love letter is going to be typed and sent by email in the middle of the night. Part of the charm of love letters is they seem sincere. And nothing says sincere more than obviously hastily-written notes of undying affection, through email. People might think you are being off if you spend 6 hours making a pretty letter design or whatever, and psychologically it sends the wrong message. Sloppy emails are the best way. The medium is the message, after all, and emails are the embodiment of expressing your immediate, uncappable lovingness.

To strengthen this one, make lots of meta-level commentary about how you are writing an email. Talk about where you are, what you are doing, exactly at the moment as you write.

Example: “It’s 4:32 a.m.— geez. I am in my living room, my head hurts from missing you, and I can’t sleep.”

Might not have made this one clear above, so let me risk repeating myself: It has to be improvised. Even though your email browser has a “Save” function, you are by no means allowed to come back to this letter later. Once you sit down, that’s it. Start it, finish it.

The biggest reason for this is that once you start writing it might seem bad to you. It probably will start a little awful. But if you keep pushing, keep at it, something magical happens and you all of a sudden end up—and there is no better way to describe this—“in the zone.”

Apparently there’s some psychology to support this, too. It’s like going through all the phases of sleep; the longer you stay with a task, the more creative and active your mind gets. I notice this transformation every time I write anything. You just need a little warm up, you know?

So no matter how much you want to hit pause, you can’t. You have to keep going. Trust me on this one.

p.s. This is not a pass for grammar or spelling. You need to do at least one read-over. Nothing breaks the heart juices more than an incorrectly used “their/there”, or worse, a missing word. This will make all your hard work equal to garbage. You don’t want this.

The subject line. By far the most overlooked part of the email love letter, but in my opinion one of the most essential pieces.

I suggest writing it before you even start your letter, something kind of cryptic and beautiful, and personal. Like “Breaking through, heart beats.” See that didn’t really mean anything. But that’s not the point. The trick is to do something that feels right.

Always be open to swapping your subject line for a reference to something really cool you do in the body of the email. This happens all the time. When you are “in the zone” (see rule Number 2), and the word-fists are really pumping, you are going to say something really significant, really awesome, and it can be your new, much better subject line.

“Now that you are more than dream.” I made that one up, but you can see how it’s progressing. Kinda?


The only thing I can say is more important than the subject line without any doubt is the original, crisp use of metaphor. This is also the hardest part. You are bound to be throwing around metaphors and similes in this thing, you won’t be able to avoid that. What you can avoid, however, is the tired use of something that’s been said a hundred thousand times before you.

Here’s a good tip: if you might have read it in Shakespeare, you should not use it. Hence “pearly whites” for your beloved’s teeth. That’s just wrong.

Make something up. And be sharp. Really try to identify the image, or feeling, you are trying to express. Don’t tell him your “heart aches” when really it’s probably all in your stomach. Tell him instead: “Our love fills my stomach with a crazy, wild electricity. It’s hard to explain—but it’s there. Being numb. Being crazy. Being in my stomach.”

This includes everything from subject line, to metaphors, to the way you sign off at the end. Writing love letters is a big deal. It’s like playing a game of poker. You need to be ready to pay up on everything you say. And if it’s any good, it might have a real impact on the person you are sending it to.

So the biggest rule, boiled down, is this: If you don’t actually love this person, don’t write them anything. Just leave chocolates in their locker or ask them to a movie. The only thing you write in relation to them is a text message asking when they’re free.

Look, life ain’t easy.

Sometimes you will give so much to a person, and you will still get nothing in return. If you write enough love letters, one of these days, one of your loves just won't write you back. It's a numbers game.

But the important thing is to know how to react. If you did everything right, and everything honestly, it's going to hurt when you don't hear back. The only thing that will comfort you is this: You had no choice. You had to write your love letter, and it was absolutely beautiful that you did. No one else ever would, and only you had the courage to really tell the truth, tell them how you feel. Remember this, because the next part is hard.

If they don't write back, you cannot, no matter what, ever write them again. You did it. You told the truth. You are you. But writing again is playing a dirty game—you are going to try even harder to get a response, do even more tricks, get even better at all of the games. But if it's not there, it's not there, and you have to be careful not to turn love lettering into love orchestrating.

Your gut instinct will be to send another letter. Another gruesome, cutting little piece of protest. "Love me, I am a person and I will string all these persuasive metaphors together for you, pixel dust, for the rest of my life, if only you will write me back."

But you'll regret it as soon as you hit “Send.”

Don't write love letters to be loved back. That's the thing. Write them to relinquish all that beautiful art, all that wonderful steam and passion—but all of it has to be true. And that's the single most important part. Never write a bad love letter for the one you really love. But, even more importantly, never write a great love letter out of desperation.