Survey the District: How Long?

Dear Date the District,

OK, I feel like this is the oldest question in the book, but how long should you wait before sleeping with a new guy? Let me explain: I always wait three dates to bring a guy home. But I don’t want to sleep with him after only three dates. We always mess around, usually naked, but I stop him before he goes all the way. And then it gets weird. He either tries to go further, or just gets up and leaves, and, either way, it’s never the same after. Are guys expecting me to sleep with them on the third date? Should I just get over my prudishness?

The Not-Quite-So-Virgin Mary

It’s not how long you wait to sleep with a guy, it’s how you go about waiting.

While it’s good to postpone the inevitable, setting arbitrary rules (like the 3-date minimum) isn’t going to get you what you want. Let’s take a look at why.

First, let’s state the obvious: sex is a game. A lot of people don’t like to admit this, but it is. It's biological in its origins: guys are looking to spread their seeds far and wide to further the human race in genetically diverse combinations, while girls can only reproduce with one partner every nine months. So it makes sense that, in general, guys want to play the field, while girls are looking for something a little more stable. That means we have two different teams (men and women) with two different objectives (lots of promiscuous sex, exclusivity) and no way to compromise. Sorry, but that's a game.

Guys win this game all the time. They find a girl, convince her to play a few rounds of hide the sausage, and start looking for the next girl. Girls end up crying and wondering what went wrong.

Even girls who aren't looking for a relationship still have a hard time getting what they want. Every girl wants to hook up with someone who, at the very least, is nice to her and acts like he's interested. But because guys are less likely to get attached, they're less likely to adhere to any standards of polite behavior.

So, if you're a girl, how can you win the game?

If the object of the game, for a guy, is sex, the first step is to keep him from winning. That's right: withhold sex for as long as possible.

You seem to understand this, in theory, Mary. But you’re going about doing it in the wrong way. Inviting a guy back to your room and grinding all over him in a tiny thong and then saying, "I don't wanna have sex with you—yet" isn't withholding sex, it's being a huge cock tease. When you're practically, but not technically, having sex, guys aren't thinking, “Wow, I really respect her for holding out.” They're just frustrated. They've seen you naked, they have a pretty good sense of what sex with you is going to be like, and they're annoyed that you let it get this far and don't want to go all the way. Almost all the mystery is gone, and what little is left is irritating, not alluring.

And when you tell him things like, “I won’t sleep with you until we’re exclusive,” you’re not helping your case, either. Everyone wants what they can’t have: an expensive purse, your best friend's boyfriend, a six-figure salary with three month’s vacation. If a guy isn’t sure whether or not he’s gonna score with you, he wants it more.

Remember when you were a kid, and you really wanted the new My Magic Diary for Christmas? If your parents told you it was coming, it wasn’t that big of a deal, and Christmas didn’t seem that far away. But if you weren’t sure whether or not it would be under the tree, the days between Thanksgiving and December 25 passed by at an agonizingly slow pace. All you could think about was how cool you would look with the My Magic Diary, and how badly you wanted it.

It’s the same way with guys. If they know they can sleep with you after three dates, the game loses the excitement. And it’s like the present you knew was coming: you played with it a few times, and then you forgot about it. The guy who knows how to get what he wants will make sure he gets it a few times, but then he’ll go out and find something else that wasn’t as easy.

So keep your flirtations public for as long as possible. You can hold hands on the street. You can kiss at a bar. But as soon as you take it back to your room, everything that you won’t do becomes a tease.

There’s no magic rule for how long you should wait. My rule of thumb is: at least a month. But if you’re only seeing each other once or twice a week, you should probably wait longer.

That way, when you do decide it’s time to take it “someplace a little more quiet,” you don’t have to worry about stopping things before they get too far.