Dear Prudence

My Friend Keeps Flirting With Me, but I’m Married—With a Devastating Secret

I never expected to be in this position.

Man contemplating with his hands on his face.
Photo illustration by Slate. Photo by djedzura/iStock/Getty Images Plus.

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Dear Prudence,

I have a close male friend, “Jim,” who recently told me he’s bisexual and that he’s known this about himself for years now. We have a good relationship and have had no problems about discussing our sex lives in the past, so I was rather surprised. He’s been open about some of his new liaisons with men. He can be detailed about such encounters, and I find it sometimes turns me on. I think he might know this and that it might be intentionally flirtatious. There have also been prolonged incidental touches and unexpected shoulder rubs, things of that sort, and I have reciprocated (only since we were both vaccinated in January due to our jobs).

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I am married, and my husband and I are both gay men. We’ve been together and monogamous for 18 years. Jim knows this and is also friendly with my husband. My husband is also dying. He has about one or two years to live without a transplant, and he’s decided not to proceed with a transplant, for various personal and medical reasons. I’m the only one who knows this right now, so our other family and friends, including Jim, think my husband might get better. I’ve been taking on more caretaking responsibilities as my husband’s health declines, and we’re talking about his wishes for palliative and end-of-life care. I love him very much and am happy to do these things for him until the very end. But due to his medical issues, I have been celibate for the last two years, and that’s a challenge. Part of me wants to discuss the situation with Jim head-on and say that we’re crossing a line. But I don’t want to lose his friendship. I’ve always cared about him, but I feel more now. And I don’t want to discuss this with my husband, who’s already having to come to terms with dying in his 40s (while I have to deal with the prospect of becoming a widower in mine).

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I never expected this. We were supposed to grow old together. There is also a part of me that wants to string things along with Jim. I have this sick thought that maybe when my husband dies we could make something together in the future. Whenever I think that, I feel disgusted with myself, as if I’m a psychopath. I just don’t know how to be alone. My husband has been my only long-term relationship.

—Friend Almost Crossing the Line

Let me start by assuring you that you’re not a psychopath—far from it. You’re taking attentive, loving care of your husband, and sometimes it feels good when your slightly flirty friend’s knee grazes yours while he tells you a sexy story about his latest date. There’s nothing wrong about any of this. You’re not betraying your husband by experiencing attraction or missing sex, and while it feels painful to catch yourself imagining the possibility of openly avowed flirtation after your husband’s death, it’s not because you’re indifferent to his suffering or can’t wait for him to die. You’re trying to find peace and consolation in an incredibly painful, traumatic time. Since you can’t discuss this with your friends and family without revealing too many details about your husband’s prognosis, you might want to look for a local support group for spouses of terminally ill patients, where you can safely expect confidentiality, as well as the relief of knowing everyone else in the group can relate to what you’re going through and won’t judge you for experiencing desire.

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I don’t think what you’ve described as passing between you and Jim necessarily requires a direct intervention, unless you fear that without one you’ll start looking for excuses to push the boundaries further. But neither do I think that if you were to raise the subject with him that you’d risk losing his friendship: “I don’t know if you feel the same, but I’ve felt a slightly more flirtatious edge to some of our conversations lately. I don’t think there’s anything wrong with that, but I also don’t want to take it any further. I realize it’s a little awkward to bring this up now, and I’m sorry if this seems presumptuous or out of left field; I don’t want to assume you’re experiencing these conversations in the exact same way.” That’s not a friendship-ending rebuke, nor an accusation of attempted seduction on his part, merely a tranquil acknowledgment that something has recently changed. I also hope you’re able to find the time to discuss your feelings about celibacy, if only in a general sense, with your husband—not because you have to confess anything to him, nor because you need him to come up with a solution to the problem of balancing monogamy with circumstantial celibacy and a terminal diagnosis, but because it’s part of the conversation of end-of-life care and something that matters to the both of you. Good luck taking care of your husband and taking care of yourself.

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Help! I’m Asked to Cite Evidence Every Time I Talk to My Husband.

Danny M. Lavery is joined by Leigh Bardugo on this week’s episode of the Dear Prudence podcast.

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Dear Prudence,

My girlfriend, “Jane,” and I have been officially dating for almost a year. She is beautiful both inside and out, and I see a real future for us. Recently, however, we have hit a major roadblock. I work in tech at a startup that requires me to take calls even on my off days. This job pays very well, and these calls are not optional. Jane works in health care and never brings work home with her. Sometimes when we are together, a call will pop up and I have to address it, if only for a couple of hours.

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When this happens, Jane gets very upset. She says that it’s not fair to her to get excited and plan for us to be alone without distractions, only for me to take these calls. I’ve told Jane that this is not something I can control and they’re not going away for the foreseeable future. These calls will also be the main source of income for our family one day. I want Jane to support me instead of making me feel guilty for doing my job. I’ve tried to explain this every way imaginable, but I can’t seem to get through to her. Am I the bad guy for not setting clearer expectations around my work and our life balance? How do I keep taking these work calls before she eventually starts ignoring mine?

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—(Always) Taking the Call

If you’ve told Jane that you’re required to take these calls for work and that this is unlikely to change anytime soon, I don’t think you’ve been insufficiently clear, although it might be time to have a big-picture conversation about whether she can accept the idea of a future together where this dynamic remains unchanged. Agreeing that this isn’t especially fair to either of you seems like a relatively straightforward concession to make. She’s right, and it isn’t, but it’s also part of your job, and you have to keep taking those calls, fair or not. This might mean making more contingent plans together and finding other ways for her to deal with her frustration over your unpredictable schedule besides getting upset with you every time your phone rings. You can stress that your request for her support is not a demand that she feign cheerfulness over these calls. She doesn’t have to like it! You just want her not to quarrel with you every time it comes up. If she doesn’t think she can commit to that—or if she says she can but then doesn’t actually follow through in practice—take that as an indicator that this may be a sad but unsolvable deal-breaker.

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Dear Prudence,

I’ve been with my husband for 10 years, and we are both in our 30s. Our sex life has been waning for a while and is now practically nonexistent. This has been going on for years. I’m the one with the higher libido who initiates the most and is often turned down. I’ve previously mentioned the possibility of opening up our relationship and have been reading up on nonmonogamy. Recently, my husband has become more open to the idea. For most of the time we’ve known each other, he’s had an appreciation for women’s fashion, but in the past year this has gone from occasional to almost exclusively around the house. I want to support him in this, but I don’t feel supported by him in return. I know that cross-dressing and nonmonogamy are not the same thing, but I feel frustrated that he can explore things so openly and readily, while I can’t explore my needs and interests outside of reading books and discussing it theoretically until he’s OK with it. I am seeing a therapist, but I feel at wit’s end.

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—Cross-Dressing vs. Nonmonogamy

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I think you’re right not to treat these two interests and possible identities as the prelude to a quid pro quo arrangement, and should continue to discuss them as separate, largely unrelated issues, since otherwise you run the risk of getting into a transactional mindset like, “You got to wear X for Y hours this month, which entitles me to three first dates.” Such a mindset, I fear, will only lead to increased distance and frustration between the two of you. You don’t say much about your husband’s concerns about nonmonogamy, so I’m not sure what becoming “more open” to the idea looks like. Is he willing to give it a test run in the near future? Have you two discussed the possibility of seeing a therapist together? Does he know that you’re at your wit’s end, or have you held back that information for fear of what might happen if you’re truly honest about how much you want this and how frustrated you’ve become with your sex life? For your part, what does supporting his cross-dressing look like? How much effort does it require of you?

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It sounds like what you want to say to your husband is something like, “We’ve been talking about nonmonogamy as a possibility for a while now, but I want you to know that it’s feeling increasingly urgent for me. I’ve been unhappy with our sex life for years, and I want to have sex more often. If you don’t think you’ll ever be comfortable with a nonmonogamous relationship, then we need to have a different conversation, because I’m not sure how much longer I want things to continue as they have been. This is really important to me, and I want to start talking about terms, limits, and a real timeline.” You have a right to push for this conversation and to ask for what you want, even if your husband doesn’t want the same things, without needing to justify your request by saying, “Look at how much I’ve supported you when it comes to clothes.”

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More Advice From How to Do It

An occasional time-waster of mine is to go into random text-only chat rooms and spin a fantasy for a willing woman. It’s fun and creative and everyone has a low-commitment good time (I hope). Recently, someone online asked if I would do a “losing her virginity” scene with her. I said sure, and I took her through a very sweet and consent-filled fantasy where she got to direct the action and feel like a star. At the end of it, she confided in me that she is actually 16 and really a virgin and also, would I want to meet up to do this for real? I of course said that I didn’t think this was a great idea but that she would make a great partner for someone someday. (I am well over 16.) But now I’m conflicted and totally gun-shy about going back online. I know, of course, that whoever is on the other side of the chat could be a boy/girl or a nonbinary/furry person of any age or orientation, but this definitely made me uneasy. Did I do a wrong thing? Is there a better way to proceed? Or should I just be happy she had a nice experience in her own home with a faraway guy who hopefully gave her a template for how it could go when she finally finds herself ready to have sex?

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