How to Write a Memorable Love Letter

For Valentine’s Day, we searched the country for inspiring love notes—and asked Bill Shapiro, editor of a book of love letters, for advice on writing one that’s a keeper.

By Rory Evans | February 2010
How to Write a Memorable Love Letter

PLUS: 9 Love Letters That Will Melt Your Heart

You started collecting love letters four years ago. How do you write one that stands out?
A great love letter is personal, with something that refers to your secret history together. If you always go to the same diner on Sunday morning, get one of its paper place mats and write your letter on that; it’s a reminder of a shared moment. You also want unguarded honesty—really let your emotions fly. And maybe this is most important: Your letter doesn’t have to be for a particular occasion. Three weeks before Mother’s Day. Tuesday the 12th. It means even more when it’s not expected. Then it’s an uncontrollable declaration of love.

What if you want to express your feelings but you don’t think you’re a good writer?
People don’t believe this, but it doesn’t matter how well you write. It’s the fact that you committed it to paper. You could draw a picture of a window and write “I love to watch you through this every day as you come home from work.” A love letter is a reflection of the person who wrote it.

Do you have a favorite kind of love letter?
I usually like the ones that are a little complicated, that say we’ve been through something together and have come out the other side, because I think that’s what love is about. I also love the starburst ones, where you feel someone’s heart exploding with joy and passion.

Do you think the space constraints on Twitter and text messages will hurt love letters of the future?
Not necessarily. You can text someone “I am thinking about your eyes” as you’re on the bus going home. It’s short, but it’s unexpected, and you can string many messages together. It’s so immediate—you’re saying, I am thinking about you right now.

So electronic love letters can be good. But do letters that are handwritten, stamped, and mailed earn extra points?
A letter doesn’t have to compete with e-mail; you can use both, at different moments. But when was the last time you got a letter in the mail? I don’t mean a bill or a catalog but a letter from a lover. That letter is now more meaningful because it’s so rare.

We know that love can be fleeting. What possesses us to write all this stuff down?
We want love to last, and we think it will. Writing it down is a hopeful act: It guarantees that in some way, it will last. It’s like taking a picture of a baby—you are capturing something you know is going to change.

It can be scary to send a love letter, can’t it?
Yes, it’s very intimate. There is always the question at the beginning of a relationship: When is it the right time to say “I love you” without getting laughed at? The risk is there, but if the feeling is reciprocated, the reward is so sweet.