Before You Pour Your Heart Out to Him, Ask Yourself This

The problem isn’t showing someone you’re interested. It’s becoming deeply invested before you know whether the interest is mutual.

This past weekend I was hanging out with a friend of mine when Aaliyah’s 4 Page Letter started playing on the radio.

I’d heard the song plenty of times before. When I was younger, I sang right along without thinking much about what she was actually saying.

But this time I really listened.

And although I still like the song, I found myself thinking: this may not be the best relationship advice.

The premise is pretty simple. She likes a guy, she’s too shy to tell him, so she decides to write him a four-page letter explaining how she feels.

And that’s where I started thinking.

What’s Wrong With a Four-Page Letter?

Absolutely nothing if you’re writing a college application, a business proposal, or making the case for getting your child into a competitive private school.

But four pages confessing your feelings to someone you’re not even sure likes you?

That’s a lot.

And the problem isn’t that a woman should never tell a man she’s interested.

The problem is investing four pages’ worth of emotion into a relationship that hasn’t actually happened yet.

That’s an important distinction.

There’s nothing wrong with smiling at someone you’re attracted to, starting a conversation, flirting a little, or even letting someone know you’d be interested in getting to know him.

You can give your interest somewhere to go.

But after that, you also need to leave enough room to discover what he wants.

Don’t Confuse Expressing Interest With Proving Your Worth

One of the things I believed strongly when I originally wrote this article was that women shouldn’t pursue men because “men love the chase.”

I don’t think that’s the most useful way to explain it anymore.

The bigger issue isn’t who technically makes the first move.

It’s reciprocity.

If you’re doing all the initiating, all the reaching out, all the planning and all the emotional revealing while trying to get someone to see how wonderful the two of you could be together, you aren’t getting much opportunity to learn how interested he actually is.

You’re giving him all the answers instead of gathering information.

Show some interest.

Then watch.

Does he move toward you too?

Does he initiate conversations?

Does he look for opportunities to spend time with you?

Does he seem curious about you?

Does his effort grow as yours does?

That’s much more useful information than whether you managed to convince him to give you a chance.

Be Careful About Falling for the Relationship in Your Head

There’s another problem with the four-page letter that I still think is worth talking about.

When you write pages and pages about someone you barely know, chances are you’re not only writing about him.

You’re writing about what you imagine the two of you could be.

You’ve already started constructing the relationship.

Maybe you’ve imagined how he would treat you, what dating him would feel like, the conversations you’d have or how happy you’d finally be if he liked you back.

But those are still your thoughts.

You don’t know yet whether the real man can live up to the relationship you’ve created in your imagination.

And the more emotionally invested you become in that imagined relationship, the harder it can be to pay attention to what’s actually happening.

Instead of asking:

How can I get him to like me?

Try asking:

What is he showing me about how interested he actually is?

That’s a very different question.

But What If I Already Know Him?

Knowing him changes some things, but not the basic principle.

A heartfelt letter inside an established, reciprocal relationship is completely different from pouring your heart out in hopes that your feelings will create feelings in someone else.

The question isn’t really:

Should a woman ever write a man a love letter?

Of course she can.

The better question is:

What am I hoping this letter will accomplish?

If you’re expressing love that’s already being shared between you, that’s one thing.

If you’re hoping four beautifully written pages will finally make someone choose you, that’s another.

Here’s What I Think We Really Want

When I originally wrote this article, I said women secretly wanted the four-page letter to come from him.

The roses. The chocolates. The declaration.

And there’s still something underneath that idea that I think matters.

Most of us want to feel chosen.

We want someone who doesn’t simply accept our interest but has interest of their own.

Someone who thinks about us when we’re not around.

Someone who reaches out.

Someone who makes an effort.

Someone whose feelings don’t have to be coaxed, persuaded, or carefully engineered into existence.

And sometimes, when we really like someone, we start doing more and more because we’re hoping our effort will inspire that feeling in return.

But attraction doesn’t work like an exchange:

If I give you enough love, attention and effort, eventually you’ll give me the same thing back.

You can show someone who you are.

You can make it easier for him to approach you.

You can even make the first move.

But eventually, you have to stop doing and start observing.

Because the goal isn’t simply to get the person you want.

It’s to find out whether the person you want is choosing you too.