How to Do It

I’m in an Exciting New Open Marriage. No One Told Me What It’s Like to Date Now.

A woman next to her phone number.
Photo illustration by Slate. Photo by yacobchuk/iStock/Getty Images Plus. 

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 wife and I (both women) are now in an open marriage … at least in theory. The problem isn’t our comfort levels—we love each other deeply, are both comfortable with the idea that we can venture out but that we’ll always come back to each other, and generally have pretty good communication. The problem is how to find someone else who’s interested. In the past, the most fun part of a sexual encounter for me was the build-up—the flirting and teasing when you’re not quite sure if the other person likes you back but you have reason to hope. Getting a chance to experience this more is one of the main reasons for me for the open marriage. But it also means that apps like Tinder or Bumble and other ways people date now just don’t do it for me because they’re too direct. I’m looking for a slow build with friends or acquaintances. So I guess my question is, how do I non-creepily let people I’m potentially interested in know that I’m available despite being married? We’re fine with our open marriage being relatively open knowledge, but we also don’t want just everyone to know (e.g. our bosses, grandparents, etc.). It’s important to me for consent reasons that I not hide being married—and that would be difficult to do anyway—but it seems like now people just aren’t reading my flirting as flirting anymore.

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—Open to Opening

Dear Open to Opening,

Flirting is a subtle art, and a lot of modern communication exists to bludgeon subtlety, so you just have to be a bit more blatant. Step it up. I recommend mentioning sex in passing. It doesn’t have to be directed at the person that you’re talking to, it could be a general observation or anecdote, something that says, “This lady fucks.” If someone is interested, they may take you up on that line of conversation and then you can build from there. Unless you’re being inappropriate (too much too soon, too graphic, etc.), you have wiggle room in terms of the creepy factor. This tends to depend more on the other person’s interest—welcome innuendo or suggestion is not going to be creepy, but persistently trying it with someone who clearly isn’t taking the bait will be. If you’re looking for a slow build, you have to make flirtation your medium. That means preparing to be rejected, dismissed, rebuffed, or politely ignored. It’s part of the game. You could maximize your chances in sex-positive spaces (I don’t know if you’re interested in polyamory, but a local poly group might be a great place to cast a net). Otherwise, this is trial and error, and since you’re eroticizing the trial, get out there and try it.

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Dear How to Do It,

My partner and I have a friend with benefits who we both occasionally have sex or threesomes with. We both have unprotected oral sex with her regularly, and sometimes my partner has used the same condom with both of us. We’re all getting tested regularly because of these things, but we’re wondering if stopping condom use for other sex acts would greatly increase the risk of STIs or if it would be pretty much the same as what we’re already doing.

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—Wrapped Up

Dear Wrapped Up,

So, your question is, essentially: “Condoms: Do they work?” Yes, they work. It is true that condomless oral sex is not strictly risk-free, but you should also be aware that not all sex acts are equal in terms of risk. The chances of contracting HIV through oral sex are extremely low—they’re much, much higher through vaginal penetration, and higher still through anal. This appears more or less true for bacterial STDs as well, though there’s less data on the transmission of other STDs from oral sex alone. So, even though your safety practices have been less than stringent (no shade!), it doesn’t make condoms useless. Your thinking reminds me of diet cheat-day brain: “I had lunch at Pizza Hut, so since I’m already pigging out, I might as well eat myself into a coma at the Golden Corral buffet for dinner.” That’s not logic—it’s rationalizing.

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Dear How to Do It,

Single gay man here with a question about topping. I was a top with my college boyfriend but switched to being mostly a bottom in my early 20s, since that’s what guys seemed to want from me. I’m now in my late 30s and got out of a decade-long relationship (with a guy who had a very strong preference for topping) just as the pandemic was kicking off, so I’ve been doing a lot of exploring and rediscovering what I want in bed—and the problem I’m running into now is that, while I’m very experienced as a bottom and know exactly how to please both myself and my partner, I feel a bit like a fish out of water when I’m topping. The guys I’ve screwed have all been very complimentary, so it doesn’t seem to be a problem with my technique for them, but I find the sensation … just not as intense for me.

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Also, I’m uncut and I find that if I’m pushing deep inside someone then my foreskin pulls all the way back while I’m inside to the point that it hurts—and this is a particular issue if the guy is riding me. (I’ve had a few instances of someone sitting on my dick and my foreskin being pulled all the way back while I’m inside them to the point of pain.) I’m with a new boyfriend who wants to experiment with bottoming. He’s enjoyed bottoming for me so far, but all of this is kind of playing with my head so I can’t just relax and enjoy myself when I’m topping. Do I just need to accept that topping isn’t for me, or is there something I can do about it?

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—Not a Top

Dear Not a Top,

It sounds like, given where you’re at right now, topping isn’t for you. Personally, whatever positional mode I’m in at a given time is subject to change—versatility to me means being open to going through phases, listening to your body and mind, and even considering the desires of others. (Here’s one anecdotal observation of gay culture that I think might be a maxim: those who are willing to top will top.) That you’ve performed, gotten good marks, and still aren’t quite into topping is what convinces me that you’re in a bottom state of mind at the moment. The performance anxiety and overall lack of confidence that often keeps guys from topping just does not seem to be there in your case. In my experience, something extremely gratifying about topping is pleasing the guy who’s bottoming (and any top I’ve considered good has made this a priority), and it just doesn’t seem like you’re deriving much joy from that. The equipment is working but the spirit simply isn’t there, and by God, so much of what makes a top is that spirit.

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I’m somewhat disconcerted by your reports of pain as a result of foreskin retraction. See a urologist for this, because that’s less than ideal and possibly treatable. Your foreskin may be tight, you may have adhesions, it could be irritation, or even an STD—any number of things, really. I suspect treating this may not solve your topping issue, but it should be addressed. Otherwise, don’t be too hard on yourself about topping. It’s not for everyone. Take solace in your bottoming proficiency. If you do what you love, you’ll never work a day in your life.

Dear How to Do It,

I met a man some months ago and proposed a casual sexual relationship with him. At the time, he seemed to be completely on board, and we did have sex a few times in person. But now, he seems to have become more and more averse to meeting up. (If it’s relevant, he does struggle a bit with ED during these meetups caused by what I must assume is a porn addiction—but I think I have been more or less empathetic to this and it has not been a major roadblock, in my opinion.)

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Our fling has now moved completely virtual. While sexting used to be supplementary to hooking up, it now seems to be the main course. The problem is that I genuinely don’t like sexting—it doesn’t really do much for me—but he keeps promising to meet up and then weaseling his way out of any in-person sexual contact. He’s not concerned about COVID-19, he hasn’t acquired any STIs, and I know he’s not seeing anyone else right now (at least in person), so I’m really struggling to explain this. Why is he doing this, and what do I do about it?

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—Ghostee

Dear Ghostee,

Why are you so sure that he isn’t seeing someone right now? You aren’t around him 24/7. You aren’t around him … at all. It sounds like he’s sitting on a secret, which in turn is interfering with his availability to have you sitting on his face. Even if it’s not a secret, per se, it’s some kind of issue that the casual nature of your relationship relegates to the bin labeled NOT YOUR PROBLEM. There’s a great scene in Ang Lee’s film The Ice Storm that I think about a lot, in which Kevin Kline’s character starts rambling about his life after sex with the woman he’s cheating on his wife with, played by Sigourney Weaver. Weaver’s character, Janey, interrupts him and says, “You’re boring me. I have a husband. I don’t particularly feel the need for another.” That’s the spirit. Take a note from that person who doesn’t actually exist.

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Forgiveness may be in your nature, but it mostly sounds to me like you’re really into this guy, which means you’re already betraying agreed-upon casualness (through not fault of your own—these things happen) and it could be that he’s feeling that and divesting. There is no reason to give someone a pass for habitual ditching out on plans … unless you’re super into him! And even then, you shouldn’t do it, because anyone who’s making regularly weaseling out of plans with you isn’t into you, or whatever else he’s got going on is eclipsing his interest of you. You can take the situation at face value: He wants to keep things on screens but you aren’t into that, and therefore you are incompatible. What you do about that is move on. Vamoose.

More How to Do It

I’m a 29-year-old woman with a 29-year-old straight male best friend who lives in another state. “Billy” and I became friends back in undergrad nearly 12 years ago. We clicked and just got each other. Billy can get a bit protective of me and needy, especially when he visits, since we don’t get to see each other but a handful of times a year.

I’m now dating an early 30s man whom I’ve fallen for very quickly. And there’s something he doesn’t know about Billy.

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