Help! My Friend Dressed in Drag to Meet My Conservative Parents.

Advice on manners and morals.
Aug. 11 2014 3:38 PM

Skirting the Issue

In a live chat, Prudie advises a letter writer whose parents severely disapprove of a cross-dressing friend.

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

Emily Yoffe: Good afternoon. I’m looking forward to your questions (and why are we all stuck inside on a day like this?).

Q. My Best Friend Dressed in Drag to Meet My Parents: My parents flew in to visit me this weekend, and since my car was in the shop my best friend graciously offered to drive me to the airport and pick them up. The problem is my friend is a cross-dresser and my parents are diehard conservatives. I asked my friend if he wouldn’t mind dressing in basic jeans and T-shirt and he felt pretty offended. I feel bad for asking him to dress his gender around my parents, but he is a straight male, and only dresses like a woman half the time. He showed up in a skirt and makeup! My parents stayed quiet during the car ride but I got an earful once we were at the hotel about the kind of people I hang out with and how I was raised better than that, etc. Part of me feels slighted by his silent (yet glamorous) protest, but at the same time I know I shouldn’t have asked him to hide his lifestyle when he’s the one doing me—and my parents—a favor. I’ve already apologized to my friend, but I still feel guilty and my parents just can’t seem to let this go. What should I do?


A: You’re the one apologizing, yet I think both your friend and your parents were in the wrong. Your friend is absolutely entitled to dress however he likes. But since you mention he only cross-dresses half the time, surely he decides there are occasions for which life is easier if he doesn’t put on a skirt and makeup. Picking up the parents of a friend who you know will be shocked by cross-dressing is one of those occasions. Again, it’s not your friend’s responsibility to educate your parents. But your parents’ getting to know your friend as an individual before they learn he is a cross-dresser is an opportunity lost. As for your parents, I hope you told them that you don’t want to hear their insulting comments about your friend. You can say the lesson you learned about how they raised you is to treat everyone with respect, period. You can tell them that they don’t have to educate themselves about this subject, but you won’t listen to disparaging talk about what kind of person your friend is.

Q. Not a Cry Baby: My son is currently in basic training for the Marines. I am so very proud of him, but of course I miss him terribly. At times I miss him so much but because I haven’t allowed myself to cry, I feel like I am spiraling into depression. Every time I feel my emotions coming to the surface I suppress them and tell myself that I mustn’t cry—I’ve convinced myself that what my son is going through is much worse and I shouldn’t be a cry baby. I know that is stupid, but I don’t know how to allow myself to cry. I think if I could have a good cry it would be very therapeutic. But I don’t want to be weak either. What should I do?

A: Your son is a Marine, and you are the mother of one, but that doesn’t mean you are an officer in the reserve mother corps. You are a mom who understandably had roiling emotions about your baby being old enough not only to leave, but to serve his country. Please cry, Mom! Tears are nature’s brilliant release valve—studies show that emotional tears contain stress hormones. If you keep your tears bottled up, you will not get the relief that a good cry is designed to bring. Don’t spiral down into depression, let those ducts gush. I’m sure that afterward you will be more at peace and able to cope.

Q. Online Humiliation: I am a professor who has been teaching for 15 years. When I began teaching I spent a great deal of time obsessing about my presentation of self in the classroom. End-of-semester teaching evaluations and direct feedback from students and colleagues were the cause of great consternation at times. I like to think I am beyond the self-loathing and periodic humiliation that often accompanied self-improvement, but with the ever-increasing presence of public online evaluations I find myself back at square one. Online evaluations are far more harsh than any I have previously encountered—and they are seen by so many more people, colleagues and family included. As such, zinger comments (e.g. “She swallows her own spit when she speaks” or “She thinks she’s something, but really she is a naive wishy-washy hack”) have me reeling as if I were a newbie. Do I need to continue reading these online evaluations? Or can I just avoid the cringing shame and misery by pretending they don’t exist?

A: And how anyone would like to spit on the kid who wrote that first nasty remark. I hope you know that if friends and family are looking at your ratings—and they very probably aren’t—that they would react as anyone would to the examples you’ve given. That is, they’d deplore the fact that snot-nosed, spoiled, know-it-all jerks are given a forum to vent their ugliness. Comments that you’ve cited are their own self-commentary. That is, they say more about the students who wrote them than the professor they’re supposedly critiquing. However, maybe there are some serious students who make helpful observations: “She knows her stuff, but can get diverted into digressions when people ask questions.” Or, “The term paper is an easy A, so don’t sweat it.” My suggestion is that you have a trusted person—a sibling, a good friend—vet the comments for you, and only forward the sincere and useful ones. Let’s hope you get to contemplate some useful criticism, and enjoy the compliments.

Q. Re: Not a Cry Baby: Are you sure the LW is the mom?

A: Great point! Thank you. And if it’s apt, Cry Dad, cry!



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