Dear Prudence: My neighbor likes to cross-dress. How do I interact with him?

Help! How Should I Converse With My Neighbor When He Dresses as a Woman?

Help! How Should I Converse With My Neighbor When He Dresses as a Woman?

Advice on manners and morals.
April 20 2015 3:03 PM

He Said/She Said

Prudie advises a letter writer not sure how to converse with a male neighbor whenever he dresses as a woman.

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Photo illustration by Slate. Photos by Thinkstock and Shutterstock.

Emily Yoffe.
Emily Yoffe

Photo by Teresa Castracane.

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

Emily Yoffe: Good afternoon, everyone. I look forward to your questions.

Q. Meet the Neighbor’s Alter Ego: We have a sixtysomething neighbor, Joe, with whom we exchange pleasantries when we see each other on the street. We recently realized that a woman we had started to see walking from time to time is in fact Joe dressed as a woman. Other neighbors tell us that “Jane” has appeared for stretches over the years, and acts as a completely different person—for example, introducing herself to people who already know Joe well. What’s the polite way to handle interactions with Jane? Just reintroduce myself and assume she knows nothing Joe knows? And my toddler knows Joe and will likely see the resemblance at some point. How do I manage an appropriate response on his part?

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A: Jane sounds like a lovely person, but how much more fun the neighborhood would be if Joe, when dressed as a woman, adopted the persona of Dame Edna. Jane is politely introducing herself to short-circuit the understandable confusion that may occur when people realize, or don’t, that Joe is sometimes Jane and don’t know what to do. Since you say you don’t do much more than exchange pleasantries, just follow Jane’s lead. Surely it’s fine to continue the conversation with Jane about the overgrown shrubs or the dog owners who don’t pick up after the dog that you were having with Joe. Your child is a toddler, and it will be years before he even notices—if ever—that Mr. Joe and Ms. Jane bear a striking resemblance. If he eventually does, you just say that yes, it’s true they are the same person and if Mr. Joe feels like being Ms. Jane sometimes, all your son has to do is treat his neighbor politely.

Q. Responsible for Domestic Violence?: My husband cheated on me with a married woman. She begged me not to tell her husband about the affair, claiming a violent temper. I firmly believe the other husband had a right to know—many infidelity survivors supported my feelings and affirmed my belief she was trying to cover her tracks through more lies—so I told him. He beat his wife and put her in the hospital. My husband wants to reconcile, so he doesn’t say as much, but I know he thinks I’m responsible for the married woman’s beating. It’s become a very divisive argument. I don’t feel responsible for the married woman’s beating, although I never wanted that to happen. Do I bear some responsibility?

A: I hope the cheating wife is safe because her husband is in prison. I have to disagree with your infidelity support group that the cheated-upon should all take up Edward Snowden’s mantle and reveal everything to everyone. When someone’s been cheated on, the issue is that person’s marriage, and that’s what should be attended to. You confronted the woman who was your husband’s partner, she begged you not to tell her husband because he was violent, you didn’t believe her, and told him. No, you are not responsible for the beating, but surely you can see you were the deus ex machina behind it and telling the husband was a misjudgment. Instead of defensively saying it wasn’t your fault, I think you should tell your husband that you do regret what you did. That does not clear him from what he did or make it all “even.” It just shows that you are capable of morally complicated thought. I hope you two are seeing a counselor, because if your marriage is going to be saved, you need a healthy foundation on which to build.

Q. Commitment: Two years ago I ended an almost two-year relationship with a girl I almost married. We had met at a running club, she is an engineer and I’m a doctor, and she was pretty perfect. My family and friends loved her. She was ready to get married, but I just wasn’t there yet. In fact, I wasn’t even close at the time; it just wasn’t something I was thinking about yet. Given the situation, I felt I needed to let her go. I’m now almost 33, and she is a year younger. We kept in touch on the phone for a while but not really in the last six months. We still live in the same city, and I still feel like I’m not totally ready for commitment, but getting closer. I’m pretty sure she’s still single. Is it OK for me to ask her out again, even though I’m still just generally not sure about commitment?

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A: This woman doesn’t have time to be diddled by someone for whom “pretty perfect” is not good enough. You are totally entitled to have qualms about commitment, but you have endless time to weigh your feelings about marriage. She is in her early 30s, ready for marriage, and if she wants children, she has to find a partner who shares her goal. You two broke up because you couldn’t meet her needs. If you have thought long and hard about what you want out of life and you realize you’re at the point where you want what she wants, and no one else has come along who is even close to making her feel as you did, then get back in touch. If you just want to be a jerk and waste more of her time, move on, Doc.

Q. My In-Laws Think I Should Spend Mother’s Day With Them, Not My Own Mom: My mother-in-law and sister-in-law are upset that I won’t go into the city with them and my husband from 10 to 6 on Mother’s Day. I told them politely that I plan on spending Mother’s Day with my own mom but I will pop by and say hi when they get home that evening. They say I’m being disrespectful for not spending Mother’s Day with my mother-in-law. I think I should be able to spend it with my mom. My mother-in-law and sister-in-law have started calling our house and telling my husband that I’m being a jerk. He thinks they are acting nuts. How do I handle this?

A: Your mother-in-law and sister-in-law sure have a way of making spending a day with them sound enticing! Your husband is devoting the entire day to his mother. You’re devoting the entire day to yours. That sounds like a good solution to a two-mothers-in-one-day dilemma. Surely you have caller ID, so when you see who’s on the other line, you say, “Honey, this call’s for you.” It’s great your husband is on your side, and he needs to say to his family, “Laura is spending the day with her mother. If you don’t drop the harassment immediately, I’m going to be spending Mother’s Day with her mother, too.”

Q. Re: Domestic violence: As soon as that woman knew that domestic violence was a possibility, she should have kept her mouth shut and dealt with her own marriage. She should be ashamed of herself, and you should have told her that. I don’t condone cheating, and the husband is definitely wrong, but she’s a rotten person too.

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A: Yes, I agree I should have been clearer about the letter writer not talking to the husband, especially in light of the wife’s protestations about his behavior. It seems clear the letter writer thought the wife was trying to keep her from spilling the beans to the husband, not that she thought, “Ha, I’m going to get this cheater beaten up!” But what she did was reckless, and even if the husband in question was not violent, the letter writer shouldn’t have told him. But the beating was the responsibility of the husband, and I hope the wife has helped get him into the criminal justice system.

Q. Self-Destructive Co-Worker: I work in a small office, where the primary team is made up of women in our 30s. We are close-knit, often socializing outside of work, and we bond over shared experiences—weddings! kids! family finances! dating! wine! One of these gals is on a seemingly self-destructive path: an on-again, off-again affair, leading to divorce; unprotected sex with multiple partners; questionable financial decisions, from the “petty” ($100 here, $100 there) to the disastrous (home purchase). In short, we are extremely worried, but unsure about what to do. On the one hand, she is our friend—and we care for her! On the other, because we are in fact co-workers, we aren’t sure what we can (and should) say without upsetting the business of work. Going to HR isn’t an option, because she is HR; going to our supervisor isn’t an option, because of personality complications. How can we help? Or do we stay out of it?

A: At least your office isn’t dull—the boss has a personality disorder and the head of HR is cracking up and stealing from petty cash. I’m afraid if all of you know your colleague is engaging in larceny in the office, you have an obligation to address this. If there isn’t anyone else but the boss, surely you are able to deal with the boss about crucial things, and this is one. I keep vowing to stop practicing medicine on the Internet, but it’s possible your co-worker is spiraling into mania and desperately needs a medical evaluation and treatment. Yes, this is exactly the kind of issue you take to HR, so what do you do when HR is the issue? You take it to whoever makes the most sense. Your friend needs help before she does something that permanently ruins her life.

Q. The Hills Are Alive!: I wrote in about a month ago regarding my love for my children’s former nanny Julia. I took your advice, though I was a bit more honest about what kind of dinner I wanted—and I discovered she reciprocated my feelings. We are taking things slowly and haven’t told my kids yet, but we’re both thrilled. Thank you, Prudence!

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A: That’s wonderful to hear! Thanks for writing back, and I just gave you a little nudge. Let us know if there’s more good news down the line.

Q. Re: Self-Destructive Co-Worker: Prudie, no one said the person was stealing from work—just making bad financial decisions in her private life.

A: Ah, I read “petty”—with the quote marks—as a reference to helping herself to office petty cash. Good point that I may have misinterpreted that. Yes, it’s more complicated if her behavior is not impinging on her work at the office. But since they are all friends, a couple of them need to sit down with her and say they are very concerned she doesn’t seem like herself, and they are worried she is going to get into personal or financial trouble. If that doesn’t work—and someone in the grip of a possible mental illness may not be responsive to such a talk—then they have to weigh how to reach out to and whom so that she does get the help she clearly needs.