How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!
Dear How to Do It,
My husband and I (both men) have been together and happily monogamous for 15 years. We are both turning 40 this year. Our birthdays are within a couple of weeks of each other, so if we want to do something bigger than a nice dinner out, we’ll usually combine the celebrations into one. When my husband asked what I’d like to do for our 40th, I had an answer: I’d like to have a threesome.
This is something we’ve talked about for many years. We’ve even incorporated a little light fantasy about it into our sex life, so it’s not coming out of the blue, and my husband’s not totally opposed to the idea. But, we’ve both been well out of the dating/hookup/apps/whatever pool for a long time, we’re both kind of homebodies. At nearly 40 with normal, married-people non-gym rat bodies, we might not have an easy time finding somebody who’d be into it. Sometimes fantasies are better off staying that way, right?
Here’s the twist: Many years ago, a guy that my husband worked with at the time (though not closely) hinted at being interested in doing something with both of us. He’s a nice, good-looking guy, around our age. Both he and my husband have since moved on to other jobs; the other guy no longer even works in the field, so there is no longer any professional connection. The other guy moved to another area, but one that we could easily travel to. He and my husband are still social media friends, so while there hasn’t been any close contact in years, they’re still in a sort of orbit where making contact wouldn’t be difficult or too weird. But my husband is (understandably) not at all sure how to start such a conversation. Plus, we were all in our 20s at the time—who knows if this dude would still be interested (though we have to remind ourselves that he’s exactly as much older now as we are).
Any tips on how to non-awkwardly, tactfully approach a not-too-close acquaintance about a threesome? Or other avenues we should pursue if this one is a bad idea or turns out to be a dead end? We have a few months before our big days.
—Birthday Boys
Dear Birthday Boys,
This is an extremely achievable endeavor, so much so that the biggest hurdle might be yourself. Approach it with no negative self-talk. Do not undervalue yourselves. Being 40ish is hardly a liability in today’s sexual marketplace. I imagine that it never really was, but has become even less so because daddy thirst is so mainstream. Being a couple can also increase your chances—many guys specifically crave group play and it’s not unheard of for an average-looking couple to bag a conventionally hot third. Non-gym rat bodies are also a norm—don’t let your self-perception stop you from approaching anyone you might find hot. Self-confidence goes a long way toward filling out a guy’s attractiveness. It could compensate for what you believe are your least appealing physical qualities.
Absolutely approach the guy that your husband worked with. Have your husband slide into his DMs. After briefly reacquainting and exchanging pleasantries, he should get right to it: You guys were talking about how hot he is and were wondering if he’d like to join you for some fun. The transition from, “Hi,” to, “Let’s bone,” can be smoothed out by complimenting his recent pics (“You are looking just as good as you did 20 years ago”). If it feels more comfortable, your husband can be a bit coy and dance around it a bit, but I think direct is always best. Men often find it easy to talk to each other on this level and it saves time. If the potential third is interested, you can start planning. If not, move on.
Understand that when you put yourselves out there, you are risking rejection. Not a big deal. It happens. Everyone gets rejected at some point. Don’t take it as an indictment of your collective appeal; you just don’t do it for that one person. Taste varies. You can easily look for potential thirds online. Feeld is ethical non-monogamy central, in terms of apps, but you can find plenty of couples on Grindr, Scruff, Sniffies—virtually any venue of online cruising has its share of guys who are looking for guys together. Don’t count out gay bars/clubs either. Just make sure you carry yourselves with confidence, no matter the venue.
—Rich
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