world of men's style / fashion / grooming

An UrbanDaddy Publication

The Gentleman’s Guide to Sleeping with Exes

Sex with an Ex

As happenstance would have it, one day you might run into that girl you dated sophomore year. Or post-college for a month or two. Or whenever. And after a quick catch-up over coffee, she’ll invite you to dinner. But you’ll just know she doesn’t mean dinner in the traditional sense.

Though food might still be involved, if you remember correctly.

Wait, why did you break up again? Doesn’t matter. You’re both single, and over each other, and she’s got legs till Saturday. This is your moment. Do something crazy. Hell, maybe even call it “closure.” But before you go ahead and bury the hatchet, so to speak, we’d like to set up a few guidelines to help you survive such a risky endeavor unscathed. Besides, we wouldn’t want this to end like last time, now would we?

For that express reason, we’d like to present to you: The Gentleman’s Guide to Sleeping with Exes...

Disclaimer: Do not, we repeat, DO NOT go bumping uglies with the girl who never got over you. That’s just cruel, and you should be truly ashamed for even thinking about it. Also, since the opposite can be just as brutal, proceed with extreme caution if it’s you who still holds the emotional torch. Actually, don’t. Instead, how about you get on home, take a cold shower and shake the notion that anything could have come of this.

Rule #1: Outwardly Acknowledge the Hilarity of the Situation. Objectively, everything that’s happening is funny. Just think: however many years ago, you crazy kids broke up because of one reason or another, and now here you are, together again. Naked. And that history could make things horribly tense, unless you cut it off at the pass and laugh accordingly. If you’re both in the same place emotionally, she’ll recognize the humor. If not, well... red alert.

Rule #2: Speak Candidly. If this were a first date, you’d want to keep the conversation focused on the future. What she likes to do, hopes, dreams, aspirations—really anything but the past and her ex. But this isn’t a first date. And you are her ex. So talk about whatever you’d like. Maybe the conversation will drift to the women you’ve dated since her, or the guys she’s dated since you, and that’s not the worst thing. Treat the whole conquest like a customer feedback survey, and you might actually walk away with a few objective criticisms that you’ll then be able to work on for the next go-round.

Rule #3: Speak Up. While some time may have passed, you’ve both been here before. You know the things she does, or did, that drove you crazy in both the best and worst senses, and you’re not trying to get back together now—why sugarcoat the exchange with pleasantries? Make the most of your poor choices by letting her know exactly what you like.

Rule #4: Take a Moment to Appreciate What’s Changed. You’ve got some new moves. She’s got some new moves. And in the time since you were a couple, you’ve both gotten a dash more swagger when it comes to business in the bedroom. Take it all in and smile, just in case the opportunity doesn’t arise again.

Rule #5: Don’t Forget the Past. Remember, you broke up for a reason. Sure, that reason probably wasn’t the sex (otherwise you wouldn’t be where you are right now), but at the time, something concrete that drove you apart. Keep that in mind postcoitally, and try not to get attached. Again, that is.

As they say, fool me twice...