Dear Prudence

Drag Queen Daddy

How do we explain my husband’s cross-dressing to our child?

Emily Yoffe recently chatted online to give advice on readers’ holiday-related quandaries. Read the transcript.

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Dear Prudence,
I have been happily married for several years, and we are expecting our first child. The only problem is that my husband is a cross-dresser. This is a fetish that I know he could never give up. We keep this behind closed doors so as not to alienate friends and family and to keep his work associates from finding out (if they did, he could lose his job). Our question is how do we incorporate this facet of our life with a new child? If we keep it hidden, our child will most likely find out someday—when mom is doing the wash for two dress sizes—and then feel betrayed and hurt. If we keep on as we are, then our child will likely tell someone that daddy wears dresses, and it wouldn’t be fair to burden anyone with that secret. What is the best thing for us to do?

—Daddy in Dresses

Dear Daddy in Dresses,
I know that when you’re expecting, you feel a need to get everything perfect for your new addition, but you’re getting way ahead of yourself if you think you should dress a teddy bear in a peignoir so you can start explaining to the baby that, just like Teddy, Daddy likes to wear pretty ladies’ clothes. Let’s say you two were into bondage and had a closetful of whips and chains. I would advise you to keep the closet secured and get a heavy-duty lock for the bedroom door, rather than try to “incorporate this facet” of your life with your child by teaching your toddler how to snap Daddy into handcuffs for Mommy. If your husband lounges around at home every night in a bustier, palazzo pants, and a wig, then I’m voting for repression. It’s time for your husband to limit his dressing up to times when he’s not with the baby. As your child gets older and mobile, your husband will have to take more steps to separate his fetish from your family life. Perhaps he will need to check into a motel occasionally when he just can’t stifle the need to dress up as Madonna. Your husband has to live with this compulsion, but surely you both want to do your best to keep your child from growing up amid such sexual confusion. You feel this aspect of your private lives is none of your family’s business, or your husband’s colleagues’, and that is an excellent attitude to maintain with your child.


Dear Prudence Video: Difficult Dinner Guest

Dear Prudence,
My dear, highly educated husband has written a book. While he has many talents, writing isn’t among them. He paid someone to edit the book, which helped it somewhat, but it’s still awful. I’ve gone through it as well and cleaned it up the best I could without completely rewriting it. The problem is my attitude—I don’t feel it’s my place to crush my husband’s dream but find it hard to just sit there with a smile on my face while he goes on and on about how life will change when he’s a best-selling author. It’s not going to happen. I realize that at one point a publisher (or a stack of rejection letters) will make the point without me doing so, but I’m not quite sure how to act now. I love him and want to be supportive of him following his dreams, but I don’t want him to waste his time. Do I stand by and lie, or break the news to him somehow?

—Vanity Press

Dear Vanity,
Watch out, Malcolm Gladwell, you’re about to be knocked off the top of the best-seller list by Tales of an Actuarial: Stochastic Models and Distribution Parameters. You say you don’t want your husband to waste his time, but he’s already written the thing, and if it’s as bad as you say, the time’s already been wasted. But consider that while almost everyone thinks they can write a book (if you go to a bookstore you will think everyone has written a book), most people never actually do it, so give your guy credit for sitting down and putting his dream—his dreary, eye-glazing dream—on paper. I can’t tell if your husband’s fantasies are sweetly pathetic or disturbingly delusional. But it says something odd about the state of your marriage that you could go so far as to edit this manuscript without your husband noticing you shared Ambrose Bierce’s sentiment: “The covers of this book are too far apart.” You don’t need to crush your husband—you’re right, the marketplace will take care of that task—but you should be honest. The next time he starts talking about what he’s going to say to Meredith Vieira when she’s interviewing him on the Today show, you need to convey that the chances of anyone’s book becoming a best-seller are vanishingly small, and his are less than that.


Dear Prudie,
I come from a small, close-knit family. About two months ago, my sister’s brother-in-law did something very freakish. I was stopping by to pick up some CDs to install on my new computer, and when I arrived, I saw him peek out the window before he opened the door. To my surprise, disgust, and embarrassment, he was standing there in his underwear. He went to get the CDs and handed them to me while still in his underwear. After I left, he called and asked if I wanted to go for a ride with him on his motorcycle. I refused and have not spoken to or seen him since. We are now planning Christmas dinner at my sister’s house, and the in-laws are joining us. This would be very awkward for me and my fiance, who knows about the events. I would rather not attend and then visit my sister’s house after they leave. But my sister’s husband says that I should just get over it and attend. He feels that what happened wasn’t all that bad. But I do and would rather not see this fellow in the near future. Am I overreacting?

—Avoiding the In-laws

Dear Avoiding,
Maybe your sister’s brother-in-law was auditioning for a spot in the Guitar Hero commercial. OK, probably not. But don’t let this jerk’s appearance in his skivvies keep you and your fiance from enjoying your Christmas. (I love the touch of him calling and asking you to ride his “motorcycle.”) You can be appropriately icy to him, and if he doesn’t get the message, tell him something to the effect that if he ever tries to make a pass at you again, you and your fiance will see that he stars in a version of the “Nutcracker Suite.”


Dear Prudence,
We spend every Thanksgiving with my in-laws and my husband’s extended family. I genuinely enjoy these people, but there is something about the enforced three-day visits that drives me nuts. This year, after a very long day where I didn’t get enough sleep, I lost it and blew up in front of the group. Most of the grown-ups have told me not to worry. My problem is the niece who apparently thinks I’m mad at her or don’t like her. I can’t quite bring myself to apologize to her because she’s right—I’m not crazy about her. Over the years she’s been rude to my daughter, who adores her, and awful to everyone else, including her parents. I know I should be the grown-up and apologize, but I can’t quite bring myself to do this. Should I write to her and let her know I was in the wrong and was acting childishly?

—Lost It

Dear Lost It,
Sending a note of apology will be a great moral lesson for your niece and a psychological relief for you. She surely has picked up that you don’t like her. Unless she has a deep-set personality disorder, in some part of that fevered teenage brain she knows she is unpleasant to be around. It’s understandable that you don’t want to apologize to this brat, but that’s part of why you should. Many an intolerable teen has become a lovely adult. (Just as many have gone on to become intolerable adults.) Your niece may get the note and say, “Why should I accept this lame apology?” But maybe there will be a small glimmer of realization in her that when you behave badly you can repair it by owning up and trying to make things right. Your gracious gesture will speak more powerfully than any of the dozens of lectures on how to conduct herself she’s surely heard from the exasperated adults in her life.


Photograph of Prudie by Teresa Castracane.