Dear Prudence

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!

Q. Do I Just Vanish?: A couple of weeks ago I went out once with “Sophie,” a girl I met through friends. Although at first I was interested in getting to know her better and kept communication via texts and occasional phone calls, I just met another girl that just seems a better fit for me. I don’t want to sound harsh, but I have no intentions of going out with Sophie again. Some friends have told me that it’s more correct and gentlemanly of me to give Sophie a heads up and directly let her know that I’m no longer interested as to not give her false hopes; but some other friends say that I just have to slowly fade away (and eventually vanish) as it will be easier for both and less awkward than having “the talk.” What should I do?

A: Going out on one date, even if you’ve had occasional communication since, does not obligate you to have “the talk.” The absence of a second date speaks volumes about your level of interest. When things are so nascent and casual, either party can fall silent without being rude. But if your conversations have given the clear impression that you intend to get to know her better—and the friends who fixed you up are all waiting for the wedding announcement—then it would be more polite, especially if she initiates a text or phone call, to simply say that you’ve enjoyed her company, but you don’t feel you two have a romantic future.

Q. Re: Online Humiliation: If the prof doesn’t already spend some time talking to her class about the purpose and impact of online evaluations, that might be helpful! My typical spiel—”I’m really, very, very interested in your thoughts on the course and how to improve it! I’ve found in the past, that there’s a certain kind of student that uses evaluations to convey that they not only hate my course, but hate me personally. If you know that student, please let them know that this kind of feedback does a disservice to everyone. I know profs who no longer read evaluations because of this kind of hurtful feedback; this is really a shame, because I’ve found that honest, constructive student criticism is really essential to improving my courses!” In my own case, I’ve found that this works pretty well.

A: I like this idea, but I think the way you convey it sounds a little too defensive. I like that you say that you carefully read student evaluations and look forward to helpful insights about the class. You can add that as your comments about their work will always be respectful and on point, so you would appreciate the same courtesy from them.

Q. Not Your Sweetheart: I’m a young female in a male-dominated industry. I enjoy my job, but there’s one thing that really irks me. Older male co-workers and especially outside contractors occasionally refer to me quite inappropriately as, “Hon,” “Dear,” etc. In one instance a contractor asked, “Can I get your business card, sweetheart?” I had the card in hand and automatically responded with, “Of course. Here’s my card,” before I realized how he had addressed me. I never corrected him, but I’d like to as he’s someone I’ll work with in the future and he needs to understand that this is not OK. How do I bring this up with him now? Do you have any suggestions for snappy replies when this happens with others?

A: My suggestion is that for now, forget the snappy replies and just deal with this in a pleasant, low-key way. You are doing well in your field, which clearly needs more women, so you want to pick your spots if you’re going to call out bias. Of course, no one should be calling you Hon, Dear, or Sweetheart (unless you’re in Maryland, where everyone is “Hon”). Sure, you’re irked, but accept that these guys are speaking out of longtime habit, and likely have no idea how it sounds to you. So be prepared for the next time, even practice with a friend or in front of the mirror. Role play someone calling you “sweetheart” and your replying, with a big smile, “Dan, here’s my business card. And please call me Jessica!” Just keep smiling and repeating. Eventually this should get through to them.

Q. Re: Not a Cry Baby: When my son went to college, he was only 400 miles away from home and I could (and did) drive to see him on holidays, etc. For the first year I think I cried for the first 50 miles on the drive home. Eventually the crying tapered off and now I just tear up a little—he is doing great and so am I. But it is not easy to separate from someone who has been around you daily for 18 years—crying helps!

A: Two weeks to go until my daughter goes off to college. I’ve loaded up on the extra soft tissues and waterproof mascara.

Q. BIL Getting Too Close: My husband and I moved to the same city as his brother and wife. Since my husband is temporarily working overseas and I’m pregnant, I’m seeing them quite often, especially my BIL. Lately I’ve been feeling uncomfortable with his behavior—he’s always trying to find an excuse to touch me and makes comments that are out of line (how his brother got the hot deal, for example). I don’t know how to distance myself from him and tell my husband without making things awkward in the family. What do I do?

A: Creeps like to use the fact that their targets don’t want to make things awkward, which give them cover for getting away with their actions. Your brother-in-law has no worries about making things awkward for you. He’s inappropriately touching his pregnant sister-in-law and making sexual suggestions. Do not protect him. First of all, tell your husband what’s going on and say you want his advice. You will also be laying down the predicate of having someone know about this. If you make an accusation, people like your brother-in-law are prone to saying, “She’s the one who came on to me!” I hope your husband calls out his brother, and you certainly should, too. Next time something happens say, “Bill, don’t touch me again. And don’t make any more sexual comments.” Just for your own comfort you may have to distance yourself. And if your sister-in-law asks you why, tell her the truth about her husband. 

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