Dear Prudence

He Wears the Skirt in Our Relationship

My husband has taken to cross-dressing for fun. Should I discourage him?

Get “Dear Prudence” delivered to your inbox each week; click here to sign up. Please send your questions for publication to (Questions may be edited.)

Dear Prudence,
Since last Halloween, I’ve been wondering about my husband. We dressed him up as a bride, and he made quite an attractive woman for our age (60)—almost no one recognized him. I had the lady at my salon do his nails, hair (wig), and makeup. He is a jokester and doesn’t take life seriously, and we had a ton of fun. My girlfriends and I talked him into staying in character all weekend as a woman and had a barbecue on Sunday with a group of our friends. Since then, my girlfriends love having “her” accompany us during our outings, lunch, and golf. He seems to be enjoying it more and more and is always interested in the next get-together. He sees it as a harmless prank and a challenge to pull off. He is not effeminate in any way when not in character and never has been. His male friends tease him but also think it is a riot.

—Should I Worry?

Dear Should,
I hope your husband looks better than Rudy Giuliani during his cross-dressing forays. I myself tried to pass as a man for this Slate piece and found the experience both fascinating and disturbing. I happily retired my jockstrap after a single outing. Clearly, you were in on and enjoyed your husband’s debut—after all, Halloween is about trying out alternate identities. But now that it’s spring, it’s perfectly understandable that you’re wondering when the outings with “Mildred” are going to end. His enjoyment of this new hobby doesn’t necessarily say anything about his sexuality, but it sounds as if it is beginning to destabilize yours—especially if when you go get dressed, you find he’s wearing your favorite Wonderbra. You’re asking me if you should worry, but only you know if you are worried and feel the joke has gone on too long. If it has, tell your husband that for your sake, it’s time he gave up being one of the gals.


Dear Prudence Video: Lusty Boss

Dear Prudence,
My wife and I have been married for more than a decade and have two young children. Recently, I have suggested ideas aimed at spicing up our sex life. These are not wild suggestions, and they involve just us. (For example, I have seen couples on TV have sex with the woman sitting on a running washing machine. Like I said, nothing overly wild.) My wife always responds that she’s not interested. However, it’s the reason she gives that gets to me. “I did it with someone else before I met you. It wasn’t that great.” I have an issue with the fact that she was willing to do these things with another man and is unwilling to do them with her husband. I have expressed why this hurts. Her response is to laugh it off and say something like, “You had your chance before you met me. You should have done it then.” I’m not complaining about the number of times we have sex. It’s just that I am having difficulty dealing with her unwillingness to do with me things she did with other men. What should I do?

—Wanting More Spice Than Just Salt

Dear Wanting,
Your letter raises a number of issues: When your wife was single, did she have sex on the washing machine at the laundromat? When you suggested washing-machine sex, did you first offer to put in a load of whites? I can understand your frustration. Your wife’s response to your request that you add some variety to your lovemaking (“I did that with Sven—in 1983”) borders on marital malfeasance. Frankly, she should be glad that you want to pour the cayenne on her and are not looking to spice up your life by spending the equivalent of a mortgage payment in Room 871 at the Mayflower hotel. And her notion that trying something different to keep things interesting is not part of married life—well, does she eat the same dinner every night, wear the same clothes every day? Since you’ve brought up sex directly and been rebuffed, try another approach. Say that with all your daily obligations, you two are in a rut and suggest a romantic weekend away. These weekends tend to result in more uninhibited sex, and if that happens, tell her how much you desire her and how you still feel you two can explore sexually together. If she is not responsive to the weekend suggestion (“I told you, I already had kinky sex with Oswaldo in my senior year of college”), then you should explain that this is so important to you that you would like a third party (for therapy, not a threesome) to help you two work it out.


Dear Prudence,
My parents are divorced, and my father remarried several years ago. Every time we visit with them, my father’s wife comments that she’d like to have my two young sons visit on their own during the summer, which gets the boys excited about the idea. Although I’d like nothing more than to have some quiet, alone time with my husband, I have some issues. For one, both of them use marijuana daily. I need advice on how to tell them that this invitation, however appreciated, will not come to fruition, and it’s not OK for them to invite the boys directly or, for that matter, even mention it when they are within earshot. We do love them, illegal habits aside. So how do I say no without pushing them away?

—Avoiding the Issue

Dear Avoiding,
Unless on the first day of school you want your boys to say about their summer, “And I learned to use a bong!” you will keep them from ever being unsupervised with their grandparents. The way you address this with your father and stepmother is to say, “We love you, but you have a serious, illegal drug habit. I hope you can stop, but until you do my children will never spend time alone with you. I don’t want to have to explain to my kids why they can’t stay with you, so if you persist in suggesting in front of them that they visit on their own, we are all going to have to stop coming.”


Dear Prudence,
I spend a good amount of money on things (clothes, books, toys) for my niece and nephew. My intention was that they use them until they grow out of them, and then I would get them back for my future kids. Every time I give new items, I politely remind my sister-in-law that I would “please like this back.” Since my niece was born three years ago, I have been given only one item back. I have since discovered that she sells most of the things her kids outgrow. I understand they need to sell them to afford new clothes, but I am not made of money, either. How do I remind her that I want things returned, other than writing “Aunty wants this” on each piece?

—Not Made of Money

Dear Not,
There’s nothing more gracious than giving a gift with “Aunty wants this” scrawled across it. Re-gifting is a useful and economical practice, but you’ve taken it to a new level: ungifting. Since your sister-in-law is busy raising two children, she doesn’t have time to keep track of what outgrown toys or clothes to return to you for your yet-unconceived children. If you resent the amount you spend on gifts for the kids, then give them less. But when you give, consider it gone.


Dear Readers,

Last week, a woman wrote in to complain about her unromantic fiancé. As evidence, she cited the box of wine and garlic bread he gave her for Valentine’s Day. Many perceptive readers wrote to chide me for missing the fiancé’s literary allusion. His gift was a reference to the Rubaiyat of Omar Khayyam: “A Jug of Wine, a Loaf of Bread—and Thou.” Here’s to garlic-scented romance!