Ask Him: I Want to Get More Serious with a Guy

Q: “I have been seeing a guy for a little while now, and it’s been pretty casual so far. I am happy with the way things have been going, and the way that they are right now, but I can see myself getting pretty serious with him. I’m already at a point where I’m not seeing anybody else, and I would like it if he were on the same page. How should I approach him about getting more serious, or, I suppose, going from casual to exclusive? I’m also going out of town for almost a month soon, and would definitely like to have the conversation before that.”kristen wiig 2

A: Oh boy. It looks like you’ve reached the phase where you’re getting very closer to having the “Define The Relationship” conversation. Those can either be the best or the worst. But they have to happen eventually. If you keep it casual for too long, these pseudo-relationships have a tendency of fizzling out, leaving both people wondering what might have happened if a serious shot had been taken.

I think your best bet is certainly to have this conversation before you bounce on a trip for as long as you’re going to. If it’s not defined that you’re only coupling with each other by then, then you’re both going to assume that the other is getting it in with other partners while you’re geographically far away from each other. And this could wreck everything.

Basically, you want to lock the dude down, or at least try to, before you leave.

The best and really only way to approach him about it is directly. You need to have an earnest conversation about your desires to take things more seriously and monogamously, while ensuring he knows you’re not trying to force him into anything—that you’re just trying to gauge where he is at in relation(ship) to yourself.

Have some reasons prepared for why you want him to be the only fish in your pond, and why you prefer, when you have serious romantic feelings for another person, that you both are in agreement that you will not get fresh with outsiders.

Where should you have this conversation?

One of your homes, probably.


Well, there are a few reasons for this. Ill start with the most negative one: if the conversation goes bad to a point that the two of you decide this casual relationship has run its course and is not going to go any further, then one of you can leave without any sort of awkward scene. If you do this at a restaurant, there might be the strange lull where one or both of you wait around for the check before parting ways, maybe forever.

There is also a comfort to having serious discussions at home, as opposed to out at restaurants or wherever. People are more willing to voice their true opinion, and there’s no worry of eavesdropping outsiders. There’s a chance that if you do this in public, the man will agree too eagerly to your wishes, even if they aren’t in parallel with his own. Then he’ll reconsider and break things off with you shortly thereafter.

Now onto the good reason: if the conversation goes well, and the two of you decide you want to enter the strange, frightening, and daunting world of monogamy, then you can celebrate immediately by having wild, crazy, sensual, beautiful, celebratory sex!

Best of luck with this. I hope it all works out.

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