Dear Prudence

She’ll Come Around

Prudie advises a gay woman whose straight guy friend keeps bringing up “date ideas.”

Mallory Ortberg
Mallory Ortberg

Sam Breach

Mallory Ortberg, aka Dear Prudence, is online weekly to chat live with readers. An edited transcript of the chat is below. (Sign up below to get Dear Prudence delivered to your inbox each week. Read Prudie’s Slate columns here. Send questions to Prudence at

Readers! Ask me your questions on the voicemail of the Dear Prudence podcast. Just leave a message at 401-371-DEAR (3327), and you may hear your question answered on a future episode of the show.

Mallory Ortberg: Hi, everyone. Let us love one another for the dangers we have passed and also that we did pity them.

Q. Give it to me straight-er: I recently moved to a new state for school and became friends with a heterosexual man who seemed comfortable with the fact that I’m a lesbian. Lately, though, he’s been making repeated comments about how much we have in common, that we should be each other’s “wingman” while dating, and how we “really have to” stop doing things together that might make us seem like a couple. I don’t think we do very much that’s couple-y—we were part of a shared group Halloween costume and occasionally go grocery shopping together (always at his suggestion, which usually means we split up at the door and meet back up in the parking lot half an hour later). Normally I wouldn’t think much of this, but he also keeps bringing up “date ideas,” and two days after he described his ideal date to me, he texted to ask if I wanted to do that exact thing together. I turned him down and have avoided hanging out one-on-one with him since. Not only that, I’ve also told him I’m not interested in dating right now and have no intentions of being or needing a wingwoman. Part of me is still worried he might be forming a romantic attachment. Am I just full of myself and reading too far into things? If you share my suspicions, how can I make him back off when I’ve already spelled out the fact that this is never going to happen?

A: I just had the worst Chasing Amy flashback of my entire life. I am going to make a blanket statement: People are generally not as good as hiding their unrequited affections as they think they are. Yeah, this guy sounds like he’s forming a romantic attachment to you and trying (and failing!) to be subtle about it. I don’t think you’re too full of yourself or reading into something that’s not there. That said, I think you’ve already done everything you can, given your current parameters—you told him you’re gay, that you don’t want a wingman, you’ve turned down his offers of a nondate-date, and you’re not planning on spending any solo time together anymore. If he’s remotely self-aware, he’ll pick up on your increased distance and won’t spend (much) time offering to go grocery shopping together anymore. If he does persist, then you can get a bit firmer in turning him down.

Q. Indecent proposal: My husband and I were talking about cheating, and he let me know that he spent some time thinking about what he would do if I ever cheated on him. First he said that he loves me very much and that we should try to work it out, to fix our relationship, and to keep our little family together. However, he would have to sleep with someone else to make sure that we are equal. I told him that a spite affair wouldn’t make anything equal and would make the strain on our relationship worse. He says he doesn’t want to be a victim and would need to do this to be back on equal footing with me. He hopes I would do the same if the situation was flipped! Can you please address how silly this all is? Also, we’re not going to cheat on each other, this was one of those “are we on the same page if something horrible happens conversations.” Apparently not!

A: Honestly, bless you for sending me this (as yet) consequence-free, mildly silly thought exercise. A good relationship ought not to be based upon ensuring one has constantly received and inflicted a reciprocal amount of pain. The goal is not “I must make sure, at the very least, that my partner never suffers less than I do,” so your husband’s plan is unlikely to result in reconciliation and the mutual re-establishment of trust should this hypothetical affair ever come to pass. (If it helps, I once had a weeks-long, only-sort-of-joking quarrel with a partner about how long each of us should wait for the other if we were lost at sea, so I know the pain of getting suckered into an argument about something that will probably never happen but feels deathly important. The correct answer, by the way, is a baseline six months out of respect/odds of a miraculous ocean rescue, plus one additional week of waiting for every month of the relationship’s duration.)

Q. Baby names: My husband and I are expecting our first child together. (I have a boy and a girl from my first marriage.) We told my in-laws over Thanksgiving that it was going to be a boy and after all the congratulations, my mother in-law dutifully informed me what his name was going to be. Apparently all boys in our family are named after their maternal and paternal grandfathers, a tradition going back to the Civil War. It would be another family tradition I would be proud to carry on (I don’t have any kind of family history on my side), except my kids already have those names. I pointed out we already have a “William” and “Alexandra” so my husband and I would have to think of something else. My mother in-law told me that my kids didn’t count because they have my ex’s last name! I got really flustered and my husband and I left early. Since then, my mother in-law and father in-law have talked to relatives and sent emails referring to our baby by the “traditional” name. My husband wants to ignore them, but it really is creeping me out! This blanket refusal to consider either me or my kids has all my alarm bells ringing. I don’t want to start a fight during Christmas, but I don’t want to spring a new name on my in-laws after giving birth either!

A: This is a situation that calls for a united front and some gentle-yet-firm pushing back. Ignoring your in-laws’ plans to name your baby on your behalf is a bad strategy, and your husband should set his sights higher than mere mother avoidance. Moreover, your husband needs to make it clear to his family that he does not see your children from a previous marriage as people who “don’t count”—they’re part of his family, too. Since you’re not averse to the family tradition altogether, perhaps there is a middle name lurking somewhere among the grandparents you’d be open to using for your third child, but you should still make it clear that you’re not going to have William One and William Two. You can say this calmly and without recrimination, and you can wait until after the holidays, but you’re not going to be able to get through this without having a conversation, I’m afraid.

Q. Girlfriend’s husband drinks, gropes, suggests an illicit encounter: After five years of dismissing my friend’s husband’s alcohol-induced, groping, sloppy assaults, I told her about it. She confronted him, he told her that I am lying (other women have complained to me about his creepy behavior), and I am no longer welcome in their home. I have known my friend for over 50 years—our families were incredibly close. Now, because I spoke out, I am the one on the outside of all celebrations. For the sake of our friendship and family ties we remain friends and lunch occasionally, but I’m always sad that I can never trust her again. I even apologized to him at the time I complained because he was hurt. I was groped and propositioned and I’m the devil. We two are part of a three-woman sisterhood from childhood. My other friend says that our friendship of three was more important than insisting on some sort of apology. It makes me feel like I’m the crazy one. I am sad, but I understand that her life is with her husband. I just don’t know what to tell her. I hate her husband for making it impossible for me to spend time with my old friend without all this resentment and hurt, but I’m beginning to not like her either. She has been generous to me in so many ways. I don’t want to act as if I am not filled with gratitude for her support.

A: I’m so sorry you’re going through this. I also don’t see any way that this friendship can be meaningfully repaired. You told your friend that her husband has repeatedly groped you over the years, and she either did not believe you or chose to believe her husband’s lie in order to preserve the illusion of peace, and offered you a scaled-down version of your former friendship in exchange for your silence. How can trust and mutual respect flourish in such an environment? This is not a simple difference of opinion, or a matter of loving a friend but not especially caring for their partner. Her husband sexually harassed you for years, and she neither believed nor defended you when you told her. I understand it can be difficult to face the truth when one’s romantic partner has done something horrible, but when faced with the choice between honesty and comfort, your friend chose comfort, even pressuring you to apologize to her husband for making a claim you knew to be true. That’s unconscionable.

The fact that she is trying to maintain a relationship with you suggests to me that on some level she knows you were telling the truth—if she truly thought you were making up malicious and baseless lies about her husband, I doubt she would try to arrange the occasional lunch together. She may have been a good friend to you in other ways, but I think you are right to find yourself angry with her as well as your husband. When you needed her the most, she let you down, and I do not think you should try to preserve this friendship.

Q. Don’t want to hurt her: I was married to my ex-wife for eight years. We suffered from infertility and it basically ate away at everything. We had four miscarriages, failed IVF treatments, and spent every dime that we had on trying to have a baby. After our adoption efforts failed, I told my wife I wanted to stop—I couldn’t do this anymore. I’d rather have a happy childless life with her than drive ourselves into more misery. She asked for a divorce.

That was two years ago, and I have since reconnected with an old high school girlfriend. She is a widow with two small children of her own. For the first time in years, I am happy. We are quietly planning on getting married next spring. I will be adopting her boys. My fiancée and I are keeping this news to ourselves for the holidays. We live in the same town as my ex and run in the same circles. My question is how and what do I tell my ex-wife? It feels cruel to tell her openly and cowardly to let her find out through the grapevine. I still care about her and I don’t want to hurt her. When I run into her at the grocery store or in the park, I feel awful but I don’t know what I can do about it. Can you help?

A: Tell her you’re getting married. Don’t make a lot of assumptions about her emotional state—I imagine the last thing she would want to hear from you is pity or the belief that this news will crush her—just say, “I want you to know that I’m engaged to [X] and we’ll be getting married next year. Our divorce was painful, but I care about you as a person, and I wanted you to hear the news from me.” You don’t, I think, have to offer the detail that you will be adopting your fiancée’s sons; if your ex-wife is already aware that you’re dating a woman with children, she will be able to put two and two together. You haven’t done anything wrong, although the details of the situation may still prove uniquely painful to your ex, and the best way to handle this is to be direct and get it over with.

Q. Casually confused: I have been seeing someone in my extended social circle casually for the past few weeks. I had been interested in a relationship with her and had initially asked her out but she declined, saying she was only interested in something casual. I respected her boundaries but after a party I hosted she ended up spending the night, and a regular routine built up around it. Since then, she has more than once (sometimes unprompted) reiterated her desire to keep it casual. I get the message, though it’s a bit confusing because when we are together … it doesn’t feel like “casual” arrangements I have had in the past. My conundrum is that an old fling is visiting me. We had made plans for her to come visit long before this situation arose. It’s unclear whether this visit will be intimate but given past visits, it’s likely. Do I have an obligation to disclose or define what exactly she means by casual? Curveball: The casual girl is longtime friends with my roommate.

A: I don’t think this woman you have a casual arrangement with is trying to be confusing; any confusion seems to be originating from your end. She’s made it clear that she’s not interested in a commitment and that you two are not exclusive, and even if it doesn’t look like the casual hookups you’ve had in the past, I still think you should take her at her word and trust that she means what she says. If you want to hook up with your old fling, you have no obligation or expectation to disclose to the woman you’re currently seeing. You may, however, want to clarify with the old fling whether or not she would be comfortable hooking up given your new arrangement with a friend of hers—it would be polite and thoughtful to say, “I’d love to see you when you’re in town. I want you to know that I’m also seeing [X]—it’s a casual and noncommittal arrangement, but if it makes you uncomfortable to get together knowing I’m also seeing someone you know well, I’d be happy to do something together just as friends.”

Q. The poor and cheap at Christmas: My extended family spends money as though it grows on trees, while I’m getting my hair cut twice a year and wearing underwear that would guarantee me very poor emergency medical care. I took a huge pay cut in order to care for my children, and I’m happy to be thrifty because of what it means for my babies. The thing is, the family goes all-out at Christmas, and I’m forced to buy more expensive stuff for people who need or want for nothing. In return, I get movies I don’t watch, books I don’t read, games I don’t play, things I don’t use. I’d really rather just have my money so I can spend it on my children’s lives and maybe splurge on some new undies. The kicker is I feel like I have to pay this exorbitant rate in order for us to be a big family at Christmas. My kids love the family, and love spending time with them, but every year I panic at the huge price tag on dinner. I try to get out of it, but they are wedded to their spending style and don’t, or won’t, seem to understand how much it hurts me. How can I open their eyes?

A: It doesn’t sound as though your extended family is familiar with your financial situation, or that they’re going out of their way to pressure you to buy things you can’t afford just to keep up. Based on your letter, I’m not sure you’ve ever shared your financial concerns with them; if you find them otherwise trustworthy and open-hearted, you might feel less burdened if you were to do so. Regardless of whether or not you want to show any of your relatives your bank statement, however, I think you should make an executive decision to spend only what you can comfortably afford this year. If that means offering mostly handmade or inexpensive items, then I think you should give yourself permission to do so, and trust that your family members are not going to throw you out of their lives unless you buy them all the flashiest new hardware. It’s absolutely OK to say, “I can’t afford it.”

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