Ask a Dude: Can I Tell My Boyfriend to Hook Up with Other People?

Hi Dude!

Well here’s the deal: my boyfriend and I have been dating for a year or so. Now we’re graduating from high school and (finally!) going to college and he is going to study abroad. Since he was a virgin when we first met (yes, I popped his cherry) I think this could be a really great chance for him to have new experiences… sexy ones. I’ve always been (kind of) popular with guys so I have a lot more experience than him and so we have had some issues with his self-esteem and such.

So … how do I ask him to… you know … “explore” some new possibilities without causing a misunderstanding? I don’t want to break up with him and I really wouldn’t mind if he were to hook up another girl. Actually, I think it would help him feel less curious about how it feels to sleep with someone else. It is not as if I would let him cheat on me every time he feels like it, but (!) I think having an affair would probably help his self-steem.

Thanks for your help!
— Probably Crazy

Dear Probably crazy,
You’re probably one of the most generous girlfriends I’ve ever heard of. I mean, encouraging him to sleep with another woman to help his self-esteem? Wow…that’s so selfless. And dangerous as F*CK!

Let me see if I understand you: You want him to go abroad and sleep with other women, but you want the right to dictate he stop when you think he’s had enough new experiences. That’s, that’s what I’m getting here. Okay. So, here’s just one of several questions that comes to mind: do you get the same leeway? Oh, and then would he have the right to tell you when you shouldn’t cheat?

I’m not saying he doesn’t have an inferiority complex when it comes to between the sheets festivities but what you’re proposing isn’t just for him, it’s for you, and it’s not about creating intimacy but sidestepping it.

Maybe I’m wrong. I admit the possibility. I’m sure his inexperience and insecurity is ruining your mood. I’m sure it’s something you want him to get over. But encouraging him to chase the ball then thinking you can just yank his leash back after he grabs it and wants to play some more is ludicrous. Unless he’s some kind of sex slave. Or has an “off” button. Which would be handy for many relationships.

If you want to open things up and let him have the option of the other 30 flavors then you’ve got to accept the risks. Relationships aren’t a dictatorship (at least not healthy ones). It’s a partnership. If you want to change the terms then he’s got to have a say in the negotiations. And make no mistake, telling him that he should sleep with someone else so that he can be a better partner for you doesn’t sound reassuring or loving, no matter how much whip cream you put on top of it.

I pride myself on being a people pleaser but I can’t give you the permission I think you’d like me to. I’m not saying that polyamorous relationships can’t work, but ones that don’t start that way have a lesser chance for long-term success.

I’d really reconsider what you want out of this relationship or how much you really want it. It sounds to me like you’re trying to give him a chance to convince you to stay in it. Probably crazy, don’t treat him or yourself as possibly stupid. Tell him what you’re not satisfied with and tell him what you need: a break.

Cutting through the sh*t,
The Dude

[Isn’t he amazeballs? Sigh, we know. Too bad he’s taken. Check out The Dude’s other insights into the male mind right here.]

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