How to Do It

I Can’t Tell If It’s a Good Idea to Sleep With the Married Man Pursuing Me

I’ll admit I want to.

A man and woman looking at each other through wedding rings.
Photo illustration by Slate. Photo by LightFieldStudios/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,

Last year, I met a very interesting man at an association convention. After the day’s business, we spent several hours talking in the bar and exchanged contact info. He is married (I am divorced), so I ruled him out as a love interest from the start. He travels frequently on business with one or two visits to my city each month. Whenever he was in town, we went out for dinner and sometimes the theater or a ball game. We grew to be very good friends. One of his trips coincided with my daughter’s wedding, so I invited him to the wedding and to stay at my house (I had other out-of-town guests also). He met my family and friends and got along with everyone.

One day, he called to say he would be in a nearby city for a Friday meeting and would like to visit me over the weekend so we could take in some of the touristy things he never gets to do when he’s here on business. I agreed, but I was stunned when, the first night, he suggested we have sex. He has always described his 15-year marriage as incredibly happy and said that finding such a wonderful woman after years of failed relationships was a dream he had almost given up on. I met his wife while on vacation in their city, and she is indeed wonderful, and they have three sweet, lovely children. I told him he did not strike me as the kind of man who would cheat on his wife, and he insisted that he never has but that he has fallen in love with me. I told him I do not get involved with married men and sex was out of the question. He didn’t persist and the weekend went well, with no further mention of sex.

The next month, he showed up at my house unannounced and uninvited to surprise me for my birthday. He wanted to take me to dinner at my favorite restaurant and was miffed that I already had plans to go there with another friend. I agreed he could stay over and the next day come to the birthday party my family was holding for me. During the days he was visiting, we had a wonderful time, but each of the nights, we argued about having sex. I admitted that if he were not married, I would definitely be interested, but he is married, so I’m not! He started questioning me about all of my male friends (some married, some single) and if I was having sex with any of them (I’m not) or if I ever had (except for my ex, I hadn’t), and then said he didn’t believe me, as he claimed he’s seen them all look at me with love and longing. He questioned my relationship with my ex because we vacation together and insisted we must be having sex even though he knows my ex is gay, which is why we got divorced. This was a side of him I had never seen, and I found it unsettling. The last night he actually came into my room and into my bed and started kissing and fondling me, trying to coax me to have sex. I told him to get out, and the next morning told him we could remain friends as long as he stopped pestering me for sex. I also told him he could no longer stay at my house.

We didn’t see each other after that for two months, although we emailed about business and social things. Then one day he called to say that he had suggested to his wife that they open up their marriage, and that she did not object. Although the reason I don’t get involved with married men is that I don’t want to be part of lies and deception, I am not sure how I feel about it if the wife is OK with it. How does a couple protect the privacy of their relationship when one of them is also involved with someone else and they all know each other? What if she thinks she’d be OK with it but then she isn’t and it destroys their marriage? Or what if once my heart is engaged, he calls it off because it’s endangering their marriage and I am the one who gets hurt? And is it any of my business to know if she also has another partner? If the only other person he is sleeping with is his wife and she’s not sleeping with anyone else, I would feel safe not using condoms (I’m post-menopause and have been abstinent for several years), but not if she’s also having sex outside their marriage. But that seems like a very personal question to ask. I also am wondering if he is telling the truth about her feelings or just making it up so I’ll have sex with him. I hate to think he would be so deceptive, but his behavior when it comes to sex is much different than the trusty friend with whom I have exchanged memories, dreams and confidences.

This entire question has been on hold since the pandemic and I have thought about it, worried about it, but also fantasized about it for three months. We’ve stayed in touch by email (not phone, another thing that makes me wonder if he’s not really gotten his wife’s consent), and I agreed to give him an answer when he’ll be here again on business in July. I feel like saying yes, but I just can’t think that this will work well. Perhaps I am just behind the times, but the whole situation feels strange and wrong. I had never imagined I would do something like this but I am excited about the prospect if my doubts could be settled. What should I do to ensure I make the right decision? And do I have the right to insist that I hear directly from his wife that she consents and does not blame me for any of this?

—Not the Other Woman

Dear NTOW,

Strange and wrong is righta correct reading of the situation you’re in. End this connection as soon as possible.

First this guy tries to have sex with you when it absolutely isn’t appropriate. Then he surprises you and seems put out that you have birthday plans and tries to have sex with you again. Then he grills you about who you might be having sex with, and tries to have sex with you again in a pretty physical manner. It doesn’t matter whether his wife is OK with or even aware of the marriage now being open—this guy is not the guy.

If you felt like you could trust this guy—which you don’t, because you can’t—you wouldn’t feel the need to confirm their openness with his wife. Even then, it would be OK to ask if you wanted to. It’s kind of an awkward conversation, but it’s reasonable to want. In case you ever find yourself in a less concerning version of this situation, yes, it’s possible that the wife would be unable to realize her true feelings until a sexual act outside the couple occurred and then would need to immediately change her boundaries. It’s also possible this would summon romantic feelings inside you that would have to be navigated somehow. There are ways to deal with this in a healthy non-monogamous situation—which, again, this isn’t.

In that hypothetical, it is absolutely everyone’s business who everyone else is having sex with, for exactly the reason you bring it up—safer sex measures and harm reduction. You can’t make an informed choice without all the information, which includes the risks his other partners are taking. So you need to know what his other partners are doing and what kinds of protection they’re using. It’s also reasonable to ask how often they all get screened for STIs.

But really, please, not this guy.

Dear How to Do It,

I’ve been dating my boyfriend for about eight months, and we started off having good sex, including oral. Oral sex is the way I am most likely to have an orgasm, but it can take me a while, sometimes between 30 to 45 minutes. He’s been doing it less frequently recently, and I asked him about it. He said he hadn’t wanted to tell me this because he didn’t want me to feel bad, but since I asked, he told me that it hurts his mouth to go down on me. He said that for a week or two afterward his tongue is sore, specifically the muscle on the underside of his tongue. I didn’t know what to say to this because I’ve never heard a guy say this before. I mean, I know it’s not an easy task, and I’ve felt guilty that it takes so long when he does it. I don’t want to make him do something that’s going to hurt him, but I was surprised that it would really make his tongue sore for that long. Is this a common issue? Do you think that means that this is just off the table forever?

—How Many Licks

Dear How Many Licks,

A week or two? If he’s really in pain for a week or more after giving oral sex, I really think he ought to call his primary care physician. Muscle soreness makes sense if he isn’t used to using those muscles, but it shouldn’t take more than a week to recover from. If he’s rounding up, and it’s more like a few days, disregard that. But if he isn’t, I want to make sure there isn’t something more serious going on.

If not, your boyfriend can do tongue-strengthening exercises. In fact, practicing oral sex is probably the best way for him to build up those muscles. You’ll want to prioritize strength building over orgasms in the short term, with him paying close attention to tongue fatigue and stopping when he starts to get sore.

He also might be doing the kitchen-sink thing: Sometimes we pull out all of our combination moves at the beginning of oral sex, when both parties would be better served by a long build up and a touch of tease. Of course if he’s hammering away at you with his tongue on full speed, he’s going to exhaust himself.

Can digital stimulation be incorporated to give his mouth breaks? That might help with his stamina. And toys. There are all sorts of sex toys on the market, some of which are designed to—and occasionally succeed at—mimicking oral sex. Try a few and see if anything strikes your fancy.

Dear How to Do It,

I’m a 45-year-old woman married to my husband of 17 years. Our sex life is the pits. Really the pits! I have recently been chatting with someone from my past who admitted to having a crush on me from high school, and I him. It’s been at least five months of continuous chatting, and it has hit the point of intimacy. For years I have felt uninterested in sex, mainly because of the bad sex with my husband, and now all I can think of is making that leap and cheat on my husband with my crush, who’s in an open marriage. I love my husband—he’s a great guy and father—but I am not sexually into him. Do I go for the plunge and see or stay away?

—Angela and Jordan

Dear Angela and Jordan,

Please don’t have sex with this crush behind your husband’s back. Your husband deserves honest, forthright communication from you. Go to him and have a serious talk. Pick a time when you’re both in a good headspace—well fed, sober, calm—and start with why you’re still married to him. “You’re a great guy. A wonderful father. I love you and I love having you in my life.” Then lay it out: “You might have noticed I’ve been uninterested in sex for years.” See how he responds. If he opens up about his own feelings on sex, listen. You can also ask him directly. If he prompts you for more, dive in: “I want to open up our relationship.” Give him space to process this and sort through his reactions.

This conversation might not all happen in one afternoon. It might take a few conversations over the course of a few weeks. Your husband might be open to opening up, or he might want to keep things closed. He might need time to think through everything.

I encourage you to think long and hard about what you’ll decide if your husband won’t open the marriage. Will you continue having mediocre to awful sex with him? Will you cheat? You might have different feelings when the conversation is actually happening—but thinking through the possible outcomes and how you’ll respond can save you an impulsive misstep in the moment.

Dear How to Do It,

I am a person with a vagina, and while I enjoy a variety of sex, the only way I can orgasm is through oral. I have a great partner—he’s generous and skilled, no problem there. But one thing often makes me self-conscious and gets in the way: toilet paper. For some reason, most TP (especially “soft” varieties) seems to leave behind tiny, shredded bits on my labia, no matter how gently I wipe, leaving me unable to comfortably engage in spontaneous sex with my partner. Nobody wants to find little TP wads down there. I usually have to run off to the bathroom to check myself first, interrupting an otherwise playful moment. Is this normal? Should I try moisturizing my labia? Is it a just a TP engineering issue? I can’t be the only person with genitals who has this problem.

—TP Trouble

Dear TP Trouble,

I have experienced this phenomenon. And yes, the soft varieties are the most prolific pillers.

A warning about wet wipes: The chemicals can irritate your vulva and labia, making long-term or consistent use unsustainable.

Shower daily, obviously. When you pee, experiment with leaning forward, backward, relaxing your butt muscle, and tightening them, to see what reduces the amount of pee splash in the first place. Then dab, not wipe. We say wiping when we teach toilet hygiene, but wet labia really need more of a dabbing motion.

When you take your underwear off before sex, you can use your gusset to give yourself a quick wipe between the lips. Just be careful not to press too hard—fabric burn on delicate vulvar tissue is probably worse than the wet wipes.

You can also talk directly with your partner about this: “Hey, have you ever noticed crumbs of toilet paper in my labia?” and “Does that bother you? Do you feel comfortable telling me if they’re there so I can rectify the situation?” And then you can just segue into playful oral, confident in the knowledge that he’ll let you know if you need a rinse.

—Stoya

More How to Do It

I grew up in a home open-minded about sex, as opposed to my husband, who grew up very Christian and conservative. I was his first and only sexual experience until recently. I gave him a “hall pass” so he could experience human sexuality without the cloud of shame he was brought up with. He’s had a few really good experiences and recently not so great ones. Basically, he’s experiencing the highs and lows everyone goes through in their teens and 20s, but in his mid-40s. Then I asked to venture out myself because … hey, it’s fun! He flipped out on me. He’s a very black-and-white kind of thinker, and part of the “hall pass” was never contingent on me going out. He now feels obligated to reciprocate and said he would never have agreed to it if he had known that. He had an emotional meltdown when I went out on a dinner date with a potential partner. I decided to just let his pass run out, but I hate how this happened. How do I get past this?