Miss Information

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"My boyfriend wants to try sleeping with men. Gulp."

by Cait Robinson

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Dear Miss Information,

At 40, after a failed engagement and other also-rans, I met a man 4 months ago. Imperfect, sure. But adorable, ethical, and affectionate. And the sex? Jeepers. So what's wrong? Nothing, maybe? In contrast to my usual M.O., we moved quickly—which is how I found myself naked in his bed shortly after our meeting, listening to his tearful confessions of… the simplest way to say it is: that he wants some dick. And it terrifies him. Or seemed to.  He said, "I don't want to turn gay!" and I said, all sincere, “Be of good cheer; life is short; I've dabbled; you'll be you, whomever you do” remarks. We even talked about his “biting the bullet,” so to speak, and going out and getting his BJ on.

But that was then. And now I am falling. Which I know should reinforce my desire for his happiness.  But recently, during sex, he spoke of how we could meet a couple, get a room, switch off—and I felt scared, not titillated. It seems to me that he is perhaps on the cusp of an awakening, which I should be supportive of. There is nothing ambiguous about an erection: he is attracted to me. But as my desire is focusing on him, he is wanting something I can't provide, and which he seems to want me to help him to get. I responded honestly that day. I said I felt it was early for such an adventure, that I have seen such scenes pull couples apart. He was reasonable, said it was "mostly" fantasy, he'd be scared in reality… But it's out there. And what am I to do with it?
Not only am I at an age where there isn't a lot of time to waste (he is 36, also never married), but shouldn't I be better at this by now? When is the time for such a conversation? 
Thank you.

—Hello, Good-Bi


Dear Hello, Good-Bi,

It’s sweet you’re asking, “shouldn’t I be better at this by now?” From what I can tell, you’re doing great. Not many people can say their partner was a) nonplussed and b) supportive of their latent bisexual desires. Short of buying a strap-on and telling him to suck that, you’ve done all you can.

Before he can get to exploring, though, he needs to recognize that he’s not going to “turn gay” any more than acting on a desire to travel will turn him French. If he’s got a gay streak (and many of us do), the most that can happen is he decides he likes it. No frogs will rain from the sky; the earth won’t crack and swallow him up; he won’t magically become part of Cirque du Soleil. A tick or two on the Kinsey scale won’t change him all that much.

So, while you can’t control his deep-seated issues, you can encourage him to confront whatever demons are holding him back. Besides “turning gay” (not a thing), what is he really afraid of? What is his background like; what might be contributing to his fear? Do some searching and see if you can find a good sex-positive therapist, even if that person is only available by Skype. Do you know any bisexual men he might be able to talk to? Books and movies can also help—anything to normalize the notion that desires aren’t often black-and-white.  He should work on addressing his internal conflict before he unbuttons anyone’s pants, though: if he’s stressed and worried, the experience won’t be fun, informative, or helpful.

As for your role, there’s a big difference between “I think I might try blowing a guy,” and “I think we should have a foursome.” The former is extracurricular dabbling; the latter drags you into the picture. If you’re not comfortable with group sex, that’s your line to draw. It’s more than fair for you to be supportive of his awakening without it being shoved in your face, literally or metaphorically.

Should he decide to experiment, work together to come up with rules that protect you both, emotionally and physically. (Everybody loves condoms!) At four months in, it’s up to you to decide whether this is too much to take on. If his explorations start sowing insecurity in you, then it’s a problem. But if you’re willing to cheer from the sidelines as he does some soul-searching, more power to you both.