Dear Prudence

Help! I’m Having an Affair With My Best Friend. Should I Tell Him How Awful I Think His Wife Is?

Read what Prudie had to say in Part 2 of this week’s live chat.

A couple sits on a couch, and a woman to the side makes a face.
Photo illustration by Slate. Photos by fizkes and SIphotography/iStock/Getty Images Plus.

Daniel Mallory Ortberg is online weekly to chat live with readers. Here’s an edited transcript of this week’s chat.

Q. Sex with my married BFF: I’m in love with my best friend. He’s married. We started a sexual affair last year. (He and his wife seem to have an unofficial or unspoken understanding about extramarital affairs.) I don’t think he knows I’m in love with him, and I don’t think he’s in love with me. I want him to be happy more than anything. I’ll put his happiness over mine every time. (I’ve never felt that so genuinely, even when I was married. It is an awesome feeling.) I think he really loves his wife and he seems to want to stay married, so that’s what I want for him.

But she is not a good wife! She criticizes him in front of his friends in really emasculating ways. She rolls her eyes, uses mean words, and just generally seems to not enjoy his company. I think it’s appalling. What do I do? It’s so hard to bite my tongue. Maybe that’s hard in part because of my feelings, but it’s nonetheless hard, and other friends of his feel the same way. When I hang out with just her, I have a good time as long as she isn’t talking about him. It’s just that I think she’s awful to him. If he doesn’t mind how she treats him, then I shouldn’t mind, right? I mean, it’s not my marriage. Or do I tell her to knock it off? Or do I tell him he doesn’t deserve that? Or are there other options? I’ve gone and fallen in love, so I’m not thinking straight.

A: Yeah, I mean, I’m not so sure that your friend is a terrific husband in return. You say that he and his wife seem to have an “unspoken” understanding about affairs, which means that they don’t have an actual, real, go-ahead-and-ask-me-about-my-open-marriage understanding. Which means that he’s been cheating on her for a year! And unless you are unbelievably good at hiding the signs of love (and most people aren’t), my guess is that your friend is perfectly aware that you’re pining away for him and is very happy to keep avoiding any clarifying conversations about the nature of his relationship with his wife, his plans for the future, and any desires or expectations that you might have.

His wife may be a generally critical and unpleasant person. Or she may be an otherwise pleasant person who’s unnecessarily unkind to her husband. Or she may be suspicious that he’s cheating on her and acting out. Or she may be relatively well behaved and you’re looking for reasons to make her a bad person so you don’t feel guilty for having “unofficial or unspoken” sex with her husband. I truly don’t know! But I do know that unless your friend wants to leave his wife, it doesn’t really matter how unworthy you think she is of him.

You’ve clearly been spending a lot of time thinking about what your friend deserves from his romantic relationships. I think it would behoove you to think about what you want and expect from your romantic relationships. It’s great that you’ve already decided upon a policy of “His Happiness Comes First,” but has he ever actually asked you to fall on a sword for him? Does he appreciate and appropriately regard your desire to suffer for him? Would he, in a word, care? What are you getting out of this relationship, besides good sex and a sense of yourself as a martyr for love? What would your life look like if you let yourself want more?

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Q. Fatherless and confused: To jump right into things, my father is currently dying of Stage IV skin cancer. The disease is being held in a sort of holding pattern for the moment due to a combination of drugs, but the basic statement right now is “when this kills him” and not “if this kills him.”

The problem for me is that my father and I do not have a good relationship. In fact, we barely have a relationship at all. After my parents separated when I was 2, he seemingly decided his part was done, and we didn’t hear from him for another nine years. When he finally did reach out to me, it was (and has continued to be) very sporadic. I’ve asked him about those nine years to figure out why he didn’t want to be involved in my life, only to have him lay the blame solely on my mother.

I had thought that our relationship might improve at least a little when my son was born, only to be disappointed when my father showed even less interest in his new grandson than he did in me.

Recently, he had a bit of a scare when one of his screenings showed potential signs of the cancer having metastasized to his pancreas, a movement that would have reduced his life expectancy to months. It got me started thinking about how I want to handle his death when it inevitably comes and what I am (or am not) obligated to do. Am I a bad daughter for wanting to set the record straight with him about all the misplaced blame he’s flinging at my mother? Should I just let it go and move on? What about his total lack of interest in my son? I know I can’t force him to be interested in my son, but my father doesn’t seem to remember my baby’s name, let alone anything else I’ve told him. And finally, is it odd that, despite our lack of closeness, I’m still upset about his impending death?

A: It’s not at all odd that you’re upset at the prospect of losing your father. Even if he was in many ways a bad father, he’s still the only one you’ve ever had—of course his death is upsetting and overwhelming. If your father is not currently in a medical crisis, and he still brings up your mother in order to cast her as the bad guy (you say he’s “flinging” blame at her, which suggests to me this wasn’t a sort of one-and-done conversation), then I think you have grounds to say, at least, something like “Dad, please don’t talk about my mom this way. She’s my mother and I love her and I don’t want you to insult her in front of me.”

It’s completely up to you whether you want to talk to your father about how his reaction to your first child made you feel, or the lack of closeness brought on by his abandonment of you as a toddler. I think it would be helpful to think in advance about what your goals would be from such a conversation. Is it just to tell him the truth, even if he doesn’t respond well or agree with you? Are you hoping for an apology and acknowledgement of wrongdoing? What would it feel like if you asked for one and didn’t get it? If there’s anyone else you can talk to about your goals beforehand, that might help you get a clearer sense of whether it feels worth doing right now.

Q. Out of line? Several months ago, a work colleague of my husband’s asked my husband to give a third friend, a woman, a ride to their work because she doesn’t have a car, lives near us, and just started working with them. I was uncomfortable with my husband going out of his way to ride in a car with another woman he doesn’t know every week. They work at a university and they are professors and she is a teaching assistant.

I recently went behind my husband’s back and searched for this woman’s name in his work email. Several chats came up between him and his male colleague, discussing this woman and making sexual jokes about her. My husband hypothetically joked about bringing her favorite music and perfume in the car when picking her up and “giving her a ride” with his hands. He also wrote that it isn’t an imposition to spend time with her because she’s so beautiful. His male colleague wrote to my husband that the woman is bored in her relationship and isn’t monogamous, so my husband should give her more rides to and from work in case he gets lucky. My husband just laughed in their online chat. I’ve also found out that this woman has approached my husband to supervise her for a two-year postdoctoral fellowship and he accepted. He’s also planning to spend more time with her to collaborate on research articles.

I confronted my husband. I set an ultimatum that he not work with this woman ever, for our relationship and for professional integrity. I told him it was inappropriate, even illegal, to write sexual jokes about a colleague over work email, especially a colleague whom he’ll supervise. My husband insists that he’s done nothing wrong, he’s never cheated, and it was banter with his colleague that was in poor taste. He said he won’t rule out working with this woman because it’s good for his career and that I’m overreacting and he can’t trust me because I searched his emails. I know it was horrible to search his emails, but I can’t forget what I read. Am I out of line for reading his emails and setting an ultimatum about working with this woman? We’ve made a marriage counseling appointment, but it isn’t for several weeks.

A: They are not colleagues, not even “supervisory colleagues.” Your husband is a professor and she is a teaching assistant and there’s a significant gap in terms of authority and job security between them. If he’s using his university email to plan to sexually harass her while also supervising the next stage of her career and wielding not-inconsiderable power over her future opportunities, it’s incumbent on you to forward them to the university’s Title IX office. This isn’t just an issue of infidelity. It’s a deeply upsetting abuse of power. It’s not “lighthearted banter” to talk about a teaching assistant with a fellow professor and promising to use the fact that she doesn’t have a car as an opportunity to try to grope her.

Q. From groupie to girlfriend: I recently began dating a member of my favorite band. The community of music that they are in is a very tightknit one. Many people at their shows have become friends and family over the years, which has been intimidating to say the least. A few months back I attended my first show as a “girlfriend,” not a “groupie.” I messed up big time, Prudie. I brought along one of my best friends who has also followed the band with me over the years. At this particular show, we were able to engage in “backstage activities” prior to their set. I was in no shape to go on the floor and watch their set, but I did. I don’t remember too much of the show. Fast forward a few days. I got a message from the band’s tour manager stating that she got a written complaint about me from a woman in the crowd. (This is the tightknit-community part; everyone knows everyone.)

The manager was super upset. I cried for days about the situation and wrote an apology message to both the woman in the crowd and the tour manager. My boyfriend brushed it off and was not upset at all. I have since attended multiple shows and have kept myself in check to redeem myself as a face of the band. I have gotten to know the other guys in the band well and we are all good friends now. The problem is, the tour manager is still upset with me. We recently attended an intimate brunch for the band after a show, and each time I would come into a room, she would immediately leave. Other people in the band are starting to notice, and she has not spoken a word to me since the night of that first show. She is a very close friend of my boyfriend and the band in general. Festival season is coming up and we will be spending a lot of time together. I know not everyone is going to like me, and I’m all right with that.

However, how do I address the awkwardness of this when we will all be together so much? (I’m talking multiple day trips in a small tour bus.) Should I worry that she will tell the other band members about the message she received? Do I try to reach out to her again in person or just let it be?

A: I wish I knew more about what you did—the details of this woman’s complaint seem pretty relevant here! It’s also concerning that your boyfriend seems unbothered by whatever happened. Do you think he’s right to consider it a non-issue? Are you more upset about what you did or more upset that this woman no longer wants to be in the same room as you? Do you often consider not blacking out (I take it that’s what you mean by “backstage activities”) to be “keeping yourself in check”? Do you want to reassess your relationship to drugs and alcohol in a larger sense?

As for the short term: You’ve already apologized to this woman and she’s decided she doesn’t want to be in the same room with you. You have to respect that, even if it makes you feel uncomfortable to let her set such an obvious boundary in public. Do not reach out to her again, as she’s made it very clear that she doesn’t want to talk with you. The best thing you can grant her is her space. I don’t have a great long-term answer for how to contextualize this one incident because I have no idea what you said or did to her. But I think you should talk about this with a therapist and one or two friends who are a little removed from this music scene to get a better sense of how you can best try to make a meaningful amends and act differently in the future.

Q. Woody Allen poster dilemma: My beloved father-in-law passed away last month. We both worked at the same office. For 20-plus years, he had a poster of a famous Woody Allen movie in his office. I love this movie as well, and we would often quote lines to one another. Now that he’s gone and I helped to clean out his office, the poster has been passed along to me. My question is: I love the film and want to honor his memory and what I think may have been his wish to gift it to me, but can I display it in my office? I pride myself on being a safe space for those who wish to speak with me, but I don’t know if I can ignore the baggage that goes with the poster. Can I separate the artist’s (accused) behaviors from the film that I love and the father-in-law who related to it? Should I just store it in my home so that people won’t think that I condone Allen’s (supposed) actions? Any advice would be appreciated!

A: The question isn’t whether you can separate the artist’s behavior from his art. The question is whether you think it would make most people, especially traumatized and vulnerable people, feel comfortable and ready to share painful confidences with you if they had to look at a poster over your head featuring one of the most famous accused abusers in the world. You do not have to personally settle his culpability or what ought to happen to him. This isn’t a question of watching Annie Hall and having a complicated private conversation with friends afterward. It’s about what message you want to send in your office at work.

Q. Hairdo nightmare: My younger brother is getting married in June, and my three children and I were asked to be in the wedding party. My daughters are 10 and 6 and my son is 4. My sister-in-law-to-be signed a contract with hair and makeup stylists months ago without consulting the bridal party about the associated costs. When I learned that it was going to cost me $200 for myself plus another $100 each for my daughters, I called her and told her that I’d be happy to get my hair and makeup done at my local salon at a cost that is more comfortable for me. I let her know, politely, that it is out of my budget to spend $400 for hair and makeup for myself and two children (and my 6-year-old has chin-length hair!) but that we’d show up at the hotel all done up and ready to go, with time to spend taking pictures with the rest of the bridal party.

Prudence, she threw a fit! She told me that since I have a job, I should be fine paying for this. I should mention that I am a decade older than the rest of the wedding party, and the only one with children and a mortgage. I reminded her that she signed a contract without consulting us, and I never consented to spending that kind of money. She gave me an ultimatum that if I wouldn’t do this, I “didn’t need” to be in the party. I said nothing. Then, last week, she told me that the children and I are no longer part of the wedding party.

We haven’t spoken since, save for a nasty text from my brother, calling me a f–king b—h and a c–t for “making his fiancée cry.” How should I handle this situation moving forward? They both live in my brother’s childhood bedroom at my parents’ house (25 minutes from me, where I visit frequently). What if she asks me to rejoin the wedding party? I certainly don’t want to, but I don’t know how to gracefully handle all of this.

A: Wow! Oh, wow, your brother and sister-in-law-to-be certainly make quite a pair. They are remarkably adept at unnecessary escalations, and I think you are well out of it. Your counteroffer was extremely reasonable; while members of a bridal party are often expected to pay for their own travel and wardrobe, it’s not customary to sign them up involuntarily for an expensive salon service. And telling you that by virtue of being employed you have no right to set a budget, and to call you the C-word (!), is so far beyond the pale. You didn’t make her cry, she made a wildly unreasonable request, you politely demurred, and she lost her shit. Count your blessings and keep your distance.

Q. Re: Fatherless and confused: This article by Emily Yoffe, “What Do Grown Children Owe Their Terrible, Abusive Parents?” has given comfort to me and many people I know. It validates those of us who often feel like no one understands our feelings. And consider going to Al-Anon, where you will find people with very similar struggles with dysfunctional or neglectful loved ones.

A: That’s a great piece; thanks for resharing it. And Al-Anon or one of its many alternatives (SMART Recovery Family & Friends, HARM LESS, LifeRing, etc.) may very well prove helpful, although some of their meetings may be restricted only to those trying to deal with a loved one who suffers from alcohol or drug addiction, so be sure to clarify that before attending a meeting.

Q. Switching schools: I’ll be in ninth grade next year, and I’m leaving my school. I’m very happy about it as I love the school I am going to, but some of my teachers are acting strange about it. They seem to take it personally, making comments like “You sure you want to go there?” (rude tone, acting like she was questioning my decision) and from another teacher, “It’s so sad, you’re abandoning us, you’ll be torn from the class … ” like somehow I was doing this just to hurt her. There are those two teachers particularly, but others have said passive-aggressive things that kind of bother me. Should I just wait it out or say something? There are only eight weeks left of school, and I don’t want to make a problem, but I feel uncomfortable. Also, is it OK to wear a sweatshirt with my new school’s name on it to school? To be clear, everyone knows I’m leaving, and only some of my friends and a couple teachers (not the ones who are upset) actually know the name of the new school, but they might be able to tell. Is it rude?

A: You are certainly allowed to wear another school’s sweatshirt, but I’m wondering if part of the reason you want to wear it is to avoid further potentially uncomfortable conversations: “Look, here’s how done this deal is: I’ve already got a new school uniform, so there’s nothing to talk about anymore.” Which is again, fine and allowed, although it may actually prompt more versions of the kind of conversation you’re hoping to avoid. If your main goal is to keep your head down and make it through the next eight weeks, I’d stick to other sweatshirts, and if some of your teachers try to guilt you into staying, you can just say, “You’re kind to worry about me, and I’ll miss all of you, but I’m really excited about this move.”

Q. Not my sister’s therapist: My older sister divorced and has started dating again. She dates men who have conservative Christian values. Several times she’s reached a point in a relationship where she’s excited to have a partner and will text, call, and message me about him. She’s especially enthusiastic when it comes to the sex, which she brags about at great length and in excruciating detail.

Eventually, her new beau says something misogynistic, usually during an argument. The comments are things like she’s “used up” because she’s had sex with “too many men” or she “disgusts” them for the same reason. She forgives this treatment every time because “the sex is so good.” Eventually, they break up over some other issue. Then she wants me to help her pick up the pieces before the cycle starts again.

I’ve had emotionally and physically abusive relationships with men who said these same things. Every time we have this conversation, I experience that trauma again. Every time, I tell her that good sex doesn’t justify this kind of treatment. Every time, I tell her that if someone says something in an argument that’s cruel, it’s because on some level they feel that way. These men are telling her how they really feel. I can tell because it’s right on the tip of their tongue as soon as there’s a disagreement. I wouldn’t accept that in a relationship and I don’t think she should accept it either. I have told her this many, many times. I’m not in a place where I can afford to keep reliving my trauma to try to help her. I love my sister, but how do I tell her I’m not her relationship counselor? How do I set this boundary with her and enforce it when she’s crying and freaking out?

A: While your sister’s situation sounds distressing and upsetting, I don’t think she’s in a position where you need to feel primarily responsible for her safety. I think it’s reasonable and safe for you to tell her that you can’t help her talk through these relationships anymore as long as the organizing principle of her distress is centered around her partner’s misogyny and sexual cruelty. You’ve already tried to offer her support and advice numerous times, and it’s bringing up enough painful memories of the abuse you’ve suffered that I think now’s the time to draw that line. Tell her before she gets into a fight with her next boyfriend that you’re no longer available for these conversations; do your best to let her know calmly and without judgment that you’re not asking her to stop dating these men or even to stop discussing them permanently with you, but that you simply can’t be the one she turns to in the middle of a fight.

Q. Re: Out of line? The wife said, “I recently went behind my husband’s back and searched for this woman’s name in his work email.” If her husband said he doesn’t trust her for this, then he’s changed his email password to lock her out. “It’s incumbent on you to forward them to the university’s Title IX office.” Unless the wife forwarded them to her own email account, this is not going to happen. And if someone else forwards those emails, then he’s going to blame his wife for it anyway.

A: He may have changed it! He also may not have. If she has access to the emails, she should forward them, and if she doesn’t, she should still file a report so that the university can conduct an investigation.

Daniel Mallory Ortberg: Thanks for chatting, everyone. See you next week!

If you missed Part 1 of this week’s chat, click here to read it.

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Classic Prudie

Q. Marriage possibly ending: I have been with the same guy for six years, married for one. He has two sons from a previous marriage, and she is not in the picture. If it is relevant I’m a male too. My husband has asked me if I could accept his moving into his own apartment for a year because he has never been on his own. He says he doesn’t want us to break up, just live apart for a while. The boys would stay with me in our home, and he would take them to spend the night every so often. We would also have a weekly date night just to keep our relationship “on track.” He married his ex right out of high school, and they had children right away, so he really hasn’t ever been on his own. I have not given a response other than asking a few questions. Truthfully the idea makes me mad as hell and I just want to tell him to leave if you want and take your damn brats with you! Then I calm down and realize I can’t live without him and the boys. Or maybe I can. I feel this is unbelievably selfish of him, but I kind of understand. But the boys have already been abandoned by their mother, how would this plan affect them? I am so confused, and hurt.

And find even more letters in the Dear Prudie archive.