Dear Prudence

My Friend Won’t Stop Talking to Me About His Miserable Marriage

Are we having an emotional affair?

A man sits hunched over, his head leaning against his raised hand.
Photo illustration by Slate. Photo by Christian Lantry/the Image Bank/Getty Images Plus.

Dear Prudence,

My best friend and I have been close for about 20 years. We’re both artists in our 40s who sometimes collaborate. There has never been anything even remotely sexual or romantic about our relationship. I am happily single, and he is very unhappily married, with toddlers for whom he is the primary caregiver. His wife is brilliant and has a very high-pressure, time-consuming job. She and I are friendly but have never been especially close. I socialize frequently with him, regularly with the whole family, and sometimes just with her.

He’s very unhappy in their marriage (as is she, I think). He talks about it with me a lot. A LOT. I try to steer the conversation to other subjects, but it seems like it helps him to talk about it, and he’s so very, very sad all the time now. When I’m with her, she sometimes talks about it, but not as much. If it matters, I have never thought they were well suited—they do not share core values. While they are both beautiful people whom I adore, I have no desire to date either of them, even if they were single. I would not even consider being involved with either while they’re still married. But are he and I having an emotional affair? If yes, am I morally obligated to stop?

—Triangulation Problems

I don’t think the important question is “Are we having an emotional affair?” but “Are these endless conversations about how much he hates his marriage actually helping my friend?” The answer to which is obviously “No.” Going over and over the details of how unhappy he is with you doesn’t seem to make his marriage more bearable and only functions as a release valve so he feels like he has sufficient energy to get through another miserable day. This sounds unproductive for him and exhausting and unpleasant for you. There is a limit to even the most patient of sounding boards, and I think the two of you have reached it. Tell him: “Friend, I love you, but I can’t keep listening to you talk about how unhappy you are in your marriage. Maybe you haven’t noticed how much you talk about it, but I have, and it’s really weighing on me. I don’t know what you need to do next—talk to a therapist, hire a divorce lawyer, be honest with your wife and find a couples counselor together—but I can’t keep having these endless conversations about how much you can’t stand your wife and then also meet up with both of you for dinner. It’s putting me in a really painful situation, and while you may not intend to, you’re hurting me. I’m not going to have any more of these conversations with you.”

The important thing here is to make it clear that you will no longer be available to discuss his marriage with him, not just asking him to stop, because it’s not a favor you’re requesting of him but a decision you need to make for your own sanity. His situation may be sad, but there are actual steps he could easily take to address his sadness—and he’s not the only sad person in the world.

Dear Prudence,

My husband and I are fairly wealthy. Our son died, and his widow has mismanaged the life insurance money badly, even though it was a big payout. She will not take advice and has threatened to cut us off from our grandkids. We already have secretly made “loans” to keep them in the house, but she rejects all help. What we can do is take our grandchildren out to eat, shopping, or on vacation. It is easier to see that our grandson needs new shoes and quietly replace them than to ask his mother why his sneakers are full of holes. Everyone gets to keep their pride.

Our other son and his wife both do quite well for themselves. Their children are in private school, and they take expensive vacations. We give their children nice gifts for their birthdays and Christmas. Our daughter-in-law is very concerned about “fairness” and has brought up several times about how much time and attention (and money) we spend on our other grandkids. I tell her their father died, and we need to stay close. She just stares at me. The conversation repeats. She is the only one who sees this as a concern. Her children are teenagers and would rather spend time with their friends, not their grandparents. She rules our son and can’t keep a secret to save her life. I am tired of repeating that my son died and we want to be there for his young children. My other grandchildren have a mother and a father and everything they can possibly want. They do not need us like our grandchildren do. We are struggling here.

—Fair’s Fair

“I’m tired of reminding you that those kids’ father died, and I’m not having this conversation again with you.” Then, because it’s unlikely that merely one set-down is going to get her to stop, for every subsequent attempt she makes to browbeat you: “I’m not having this conversation again,” over and over, followed by absolute stonewalling. Leave the room if you have to, change the subject abruptly, or fake a phone call. No matter what she says and no matter how she tries to get your attention, refuse to discuss your other grandchildren with her from now until the end of recorded time. You’re not ignoring her children, and they’re not suffering from lack of grandparental affection. She’s being rude and presumptuous, and presumption requires checking, not argument.

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Dear Prudence,

My partner recently came out as trans, and it’s been very hard for me. She used to present as a very rugged, masculine man and wanted to wait until we were married to have sex. I went along with those wholesome ideals and waited because our relationship was so good and I loved how attentive she was to my family. (We both brought a child into the relationship.) After we got married, sex was very infrequent, about four times a year. I’m a very sexual person, and this was sad and confusing, but her reasons were very plausible—until, three years in, she finally told me she wanted to transition.

I’m having the hardest time, and I feel horrible about it. Seeing my spouse as a woman makes me feel panicky about sex. Trying to have sex when I feel panicky is a horrible feeling. I’ve never been transphobic, and I want to be a good ally, but I can’t get on board with this. I’m a heterosexual woman who’s never been attracted to women. But this is my partner, and she was uncomfortable having sex with me as a man. Now I’m uncomfortable having sex with her as a woman. I also feel terrible because she comes from a strict, conservative background and works in a very trans-unfriendly environment. I’m failing my spouse, and I feel anxious all the time. I’ve supported her in staying home to care for the kids and in transitioning, talking about her feelings—everything but sex I can happily and easily support. Also, I’m angry that I didn’t know why she wouldn’t have sex with me for three years. What should I do?

—Trouble With Transition

I can tell you what you shouldn’t do: Please don’t keep swallowing your own feelings because you think they make you a bad ally, and please don’t have sex that makes you feel anxious and panicky because you think it’s transphobic not to. You are not failing your spouse because you don’t want to have sex anymore. You haven’t failed her by not being attracted to women. (You do not ever have to have sex you don’t want to again.) Forcing yourself to stay silent about your sexual needs is not supportive of trans people but self-destructive and unnecessary. This also isn’t a situation where one of you has the exclusive rights to feel pain or ask for support. You can both support your wife’s transition in general and feel anger on your own behalf that you spent three years bewildered and confused about your almost-nonexistent sex life. You can have compassion for the closet she was in during those years, her repressive background, and her hostile professional environment, and compassion for yourself. You are entitled to have your own feelings about your marriage, including anger, and to find healthy, useful ways to explore and express those feelings, preferably with a therapist.

You’re a heterosexual woman, you know that you’re not attracted to your partner post-transition regardless of the love you still bear for her, and you’re trying to reason away your own anger because you think you don’t have a right to be angry. This is a recipe for a miserable marriage. That doesn’t mean you should start shouting at your wife tomorrow or withdraw your support from her, but it’s time you started being honest with both yourself and her. I think divorce will be the likeliest outcome of this conversation, but that doesn’t mean you have to start filing tomorrow or that you can’t remain friends and co-parents. The only conversation you need to have right now is about your sexual and romantic incompatibility. You and your wife each deserve to be with someone who wants to have sex with you.

Help! I Can’t Stop Snooping On My Former Job.

Danny M. Lavery is joined by attorney Jason Carini on this week’s episode of the Dear Prudence podcast.

Dear Prudence,

I’m in a happy relationship of about five months. He’s kind, considerate, and hilarious. We haven’t had any conversations about our exes. I know he’s only dated one girl before me because he mentioned it in passing. I left it alone because I figured it might be a painful topic. I was still curious, so I snooped through social media (which was a bad move on my part) and found out that they were together for at least two years, if not four or five. That seems like such a big deal! She still likes every single one of his posts. I freaked out but haven’t talked to him about it yet. It just feels like such a major part of his life is being left out of the story! I have a tendency toward anxiety and the fear that I am just a placeholder for his feelings for an ex—baggage from a previous relationship. Is it worth a conversation (and an apology for snooping), or am I better off focusing on the present and refusing to fuel my anxiety?

—Ex Feelings

While I agree that looking through someone’s Insta history is no substitute for an honest conversation, it’s not as if you went through his phone or broke into his journals. And it’s fine to ask a partner about their ex(es) in general terms. You can open with an apology, but that doesn’t mean you have to wear a hair shirt: “I’ve wanted to know more about your history with your ex, but I was too nervous to ask you about it and felt self-conscious. I saw on [social media platform] that you two were together a long time, and it seems like it was a big part of your life. I understand if you don’t want to go into detail, and I’m sorry I tried to replace having a conversation with scrolling through your post history. I shouldn’t have done that. But I’d love to hear a little bit about what that relationship meant to you, if you’re down to talk about it.” He may decide he doesn’t want to discuss her at length, but that doesn’t mean you can’t ever talk about your romantic histories ever again.

I also think it’s worth sharing with your boyfriend more about your anxieties and leftover fears from your previous relationship. That doesn’t mean you have to alert him every time you experience a flash of insecurity or that you’re asking him to fix it. But it’s good for people to let their partners know what they struggle with and what they’re afraid of so they can better ask for (and offer) emotional support, or at least provide emotional context for why they’re having a rough time. None of these conversations should be off-limits.

Dear Prudence Uncensored

“You are just being an unpaid, underqualified therapist right now.”
Danny Lavery and Nicole Cliffe discuss this letter in this week’s Dear Prudence Uncensored—only for Slate Plus members.

Dear Prudence,

I am a 28-year-old older sister to a 21-year-old who is currently living with me and has for the past three years. She has been attending community college (which I have gladly been funding) and will be transferring to a university this fall. She’s eligible for an automatic transfer to two highly regarded state schools, one in town, the other a couple of hours away. The school in town is more competitive, and she will more than likely be stuck with a liberal arts degree, which she is not excited about pursuing. The other school would be a more reasonable choice for her because she has a much better shot of pursuing the degree she is actually interested in (engineering) and in a much more supportive environment. The problem is her boyfriend. She met him at her part-time job, and while he’s a nice guy, part of the reason she wants to choose the less desirable of the two school options is because she’d like to stay closer to him. What can I do and how much can I push her to accept the other offer, the one two hours away but with so much more promising potential for her future? I don’t want to harm our relationship, but since I’ll be ponying up some of the money, I figure I should say something.

—Sister’s College Choice

You have grounds to say something regardless of how much money you’re contributing toward her education, and it’s likelier your sister will listen to you if you leave your financial contribution out of the conversation. Tell her you’d like to have a conversation about the advantages and disadvantages of each school so you can help her make an informed decision.
The fact that the engineering degree may be impossible to get at the closer school is salient, but the fact that it’s more competitive also isn’t a knock against it. I wouldn’t present it as a downside when you two are making a list of pros and cons, since that might carry the implication you don’t think she’s up to the challenge. Ask her what she thinks of each of the schools and whether it would be impossible or merely challenging to pursue engineering nearby.

You can advocate for which choice you think is best without having to bring her boyfriend too much into the conversation. If she does seem determined to stay nearby no matter what, be prepared to let it go after you’ve made the case for going as best you can. And if he does come up, don’t dismiss that concern out of hand, because that might make her feel like she has to defend him. Just say something like: “I get why you want to stay close to him, and I know how much you care about him. But if he weren’t in the picture, would you be considering the local school anyway? Do you think he’d be interested in coming to visit you regularly?” She has more options than she might think.

Dear Prudence,

I’ve been applying to jobs for many months now. I have a disability and am genderqueer. Many jobs have boxes to check to disclose a disability, which I do because I have to tell them at some point, but a co-worker at a previous job once told me our boss said she wouldn’t have hired me if she’d known beforehand (illegal but true). I have also been checking the box that says I don’t disclose my gender because there are only ever male and female options. I almost never hear back from these applications, which I know is part of applying online, but I can’t tell if I’m screwing myself over by disclosing these things about myself. Should I just check a gender box even if it’s not accurate?

—Honesty in Applying

It’s always difficult to gauge how much something like being genderqueer may affect the status of your applications because you can’t ever go back and apply as a slightly different version of yourself that’s equally qualified but not genderqueer. I’m inclined to agree that the primary reason you don’t hear back is because most job offers don’t come from online applications but through personal connections and recommendations. Which is a dispiriting thing to write! If all you’re looking for is permission to give the “M” or “F” box a shot, you have it. (I don’t think you owe a possible future employer any disclosures about your gender before you’ve even had a conversation.) But if what you’re asking is whether I think that’s going to make a difference when it comes to hearing back from prospective employers, I’m afraid I just don’t know. And you’ll still have to deal with anti-disability discrimination, which is illegal but difficult to prove at the application-screening process. I wish you all the best in your job search and hope you find something soon.

Classic Prudie

My boyfriend of two years recently told me that he lost his virginity at the age of 12 to a family friend that was 30 at the time. He swears that he is the one that seduced her and that it is a very happy memory for him; I have no reason to doubt him and he is “older” than his years and has always dated older women. But I’m very grossed out by the woman in question. I’m picturing myself allowing a 12-year-old to seduce me (I’m 30) and the thought is disgusting to me. I really don’t think she is a predator and my boyfriend really does seem to have quite an effect on older ladies—they all just want to take their pants off for him. My question is mainly that I don’t know how I’m going to face this woman—we see her about three times a year at family events and one is coming up next month. I am not great at keeping my facial features neutral so I’m worried she’s going to figure out that I know. I don’t want to “out” her. I’m definitely not going to touch a drop of booze that day because I don’t want to get tipsy and say something I’ll regret. I really just don’t know what to say to this woman or how to act in front of her!