I get a lot of positive feedback from readers on the effectiveness of my advice, which is one of my primary rewards as a blogger. But there’s one area where young women continually struggle to implement HUS strategy: No Sex Before Monogamy.

Don’t get me wrong – it’s not that women want to have sex before monogamy. They want nothing more than to have sex within the context of a relationship. The problem is that they’re often unsure about whether they’ve reached that point, and they hate, hate, hate having to initiate the DTR, i.e. “Define the Relationship talk.”

Picture this. You’ve hung out with a guy a few times, you really like him, and you think he likes you too. The attraction is strong, you’ve made out and gone a bit beyond, and you’re hoping he wants a relationship and that the two of you will be official soon. He appears to be sincere in his interest, and you’re pretty sure he’s not interested in anyone else. But he hasn’t said anything about dating, and you wish he would before he tries for sex! Because if he doesn’t, you’re going to have to call a halt in the middle of a passionate makeout and ask him, “What are we doing?” And he’ll stare at you in bafflement and say, “What? Don’t you want to?” And you’ll say, “Yes, I do, but I mean, what are we doing really? I mean, are you just looking to hook up, or…?” At which point he sighs, sits up, and resigns himself for the inevitable “talk.”

Girls need lady balls of steel to go there, because even if the guy is open to a relationship, we worry that killing the buzz this way will be such a turnoff that he’ll want to get away from us as fast as possible. So more often than not, girls go off the high dive hoping for the best. Even girls who have rehearsed the lines with me report back that they couldn’t bring themselves to say it when the time came.

Sometimes it works out and not long after having sex he states that he wants to be your boyfriend. Many times, though, sex is the Touchdown and it’s Game Over. You just don’t understand – how could a guy go from liking you so much for weeks, then pretend you’re just buddies (or even worse, strangers) when you bump into him on campus? Dammit, you should have asked him what he was looking for!
I’ve got two important pieces of information for you today – a strategy and a caveat.

Reducing the Awkwardness of the DTR
As a woman you are the gatekeeper to sex. You’re calling the shots on timing, and if you have sex without asking any questions, it’s on you, you know that. So how can you bring up the relationship question without feeling like you’re killing the mood and creating major awkwardness?

Make it short and very direct. Reader Gin Martini recalls what his college girlfriend (now wife) said:

“I won’t [hook up with] anyone who’s seeing other people. Are you?”
That won’t guarantee you a relationship, but at least it speaks to the question of being exclusive. It also provides an easy opening to the question of what each of you is looking for. Do not wait until you’re both all worked up to ask this question! When you get the sense that he’s going to try and escalate for sex, have the conversation the minute you start canoodling.

Gin Martini:
There are two valid answers you want to hear – “yes, and it stops right now,” or “no.” Why do I recommend this approach? It’s stated as a boundary, not a demand or ultimatum. It’s assertive but not aggressive or combative. There is no threatening label of boyfriend, or commitment, or exclusivity, or anything. It instantly commanded respect from me.

Every successful relationship I’ve ever seen began with a DTR that was easy, even joyous. You do not want a reluctant boyfriend. If a guy is saying, “I don’t think I want a relationship right now” or “I don’t think I’d make a very good boyfriend,” take him at his word. Run, don’t walk, away! I’ve seen women trapped in a regular hookup give the ultimatum “We’re in one, or we’re done.” Sometimes it worked, and the guy agreed to date. But in every single instance, it was a bad relationship, characterized by fights, jealousy and a lot of sketchy behavior. A guy who doesn’t want to be in a relationship and reluctantly agrees is in it for the sex alone. That’s reason enough to drive on.

A guy who likes you and wants to be in a relationship is going to happily agree to your escalating emotionally when he escalates sexually. Time after time young women have told me that when they finally met the right guy, the DTR took about 30 seconds. Both of them jumped off the high dive together.

Trust me, that’s the only kind of boyfriend you really want.