Dear Prudence

Woman on the Side

Prudie counsels a wife whose husband cares more about the woman he cross-dresses as than his family.

Mallory Ortberg
Mallory Ortberg.

Photo by Sam Breach

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

Mallory Ortberg: Hi, everyone! The New Republic is for sale today, so if anyone wants to go halfsies on it, let me know.

Q. The other woman: My husband of 10 years always liked to cross-dress; he did it when we dated and all through our marriage. It was casual, the occasional outing, a stress-reliever for him that I had no problem with. In the past year, all of a sudden he has ramped up his cross-dressing activities, ordering tons of clothes, going out at least once a week as “Pam,” and telling a few close friends of his proclivities. I know a lot of this is a reaction to our daughter we had two years ago and the new pressures and responsibility, but how do I deal with the resentment that Pam gets all his attention and his daughter and I are second?

A: There are two issues here, I think: One is that your husband is not spending enough time with your new child. This needs to have its own conversation unrelated to issues of gender expression and dress.

The other is that you two seem to see Pam very differently. To you, Pam is a stress-relieving hobby. It sounds like your husband considers Pam to be an integral part of who he is. I doubt very much that Pam is a “reaction” to the birth of your daughter. What you see as cross-dressing may very well be what your husband considers freedom. There is a difference between cis men who enjoy cross-dressing and a transwoman beginning to come out to her friends and family. The part where your husband is introducing close friends to Pam suggests to me that this is not about cross-dressing for fun every couple of weeks.

I don’t know how your husband identifies, but you two need to have a serious, loving, open conversation about it. I know what Pam is to you—an occasional distraction that pulls your husband away from what you see as his real life. What you need to find out is what Pam is to your husband.

Q. Business travel and companions? In a couple months, I’ve been given the opportunity to travel to a lovely foreign city for a business trip. The trip entails three meetings with customers at their offices around the city and no other social events. My wonderfully supportive boss has set the schedule up for me so I have the weekend and an extra day during the trip to enjoy my first time out of the country. Since I’m a relatively anxious traveler and a newer employee, would it be ethical to ask a friend to come along, provided he or she pays for his or her own flight and expenses and shares my hotel room, which I have booked and paid for but which will be reimbursed by the company. There is nothing in the company handbook about travel companions, and I would of course follow all the rules for the expense reporting.

A: This sounds perfectly ethical to me. As long as you have a friend interested in joining you on a business trip at his or her own expense, I can’t think of a moral reason not to do so. My only concern is whether your employer would think it was appropriate. You say your boss is supportive, and you sound enormously conscientious, so I think you can ask your boss if there’s any company policy on bringing guests along during business trips. If the answer is no, I hope you’re able to find alternate methods of managing your travel anxiety.

I am willing, by the way, to be chided by any business professionals reading this; if you think it’s an inappropriate request that could potentially harm the letter writer’s future at this company, I’d love to hear from you. I don’t want to make any suggestions that could cause career damage.

Q. Choking at the gate: I survived a horrible upbringing for two reasons: I inherited some money, spent on years of grueling trauma therapy, and I joined a zany theater group. These wonderful people surrounded me with love, recognized my intelligence, and urged me to pursue a college degree and a challenging career. Flash forward 10 years: After graduating at the top of my class from the best department in my field (it involves neuroscience), my business idea has attracted major investors and mentors. All I have to do is finish writing the plan, the kind of thing I can do in a week. I’ve been sitting on it for more than a year. I feel consumed with anxiety even thinking about this major change, but I’m ashamed of avoiding the challenge, too. Some outside perspective, please: How do I break this block and validate the faith of the people who have become my true family?

A: Congratulations on building what sounds like a wonderful and expansive life. You already know what it is that you have to do next. There’s not much I can do short of coming over and standing over your shoulder while you finish your business plan to make you get it done. You say you’ve spent years in trauma therapy; I wonder if you have a therapist at the moment who can help you deal with your current anxiety. You have a very specific goal you want to achieve, and I think cognitive behavioral therapy might be invaluable in helping you overcome this particular block. 

It may be that part of you is frozen because you fear losing the love and respect of the people in your life if this business doesn’t live up to its early potential. I hope very much you know that finishing a business plan is not what validates the faith your chosen family has in you; you are worthy of the love they offer regardless of what job you have or businesses you start. Whether this particular idea succeeds or fails, you are a successful person.

Q. Re: Business travel and companions? Go for it! I’ve got a work trip coming up in three months to a Caribbean island. I’m bringing my wife, kid, and parents to babysit. They just need flights.

A: That sounds delightful! I hope the original letter writer’s company is as generous as yours.

Q. Trying not to rebreak his heart: I spent several years in a committed relationship. We lived together, and our families became close. We maturely parted ways a couple years ago. He wanted marriage. I honestly never thought I would get married to anyone and felt he deserved to find someone who shared his desire to be married. He took it hard, but now we text about once a week, speak on the phone every couple of months, and he maintains a limited relationship with my family. In our time apart, I’ve fallen in love and am engaged to my soul mate. I don’t think my ex has had a relationship since we split, but we don’t talk about things like that. I’m excited about my future with my husband-to-be but don’t know how to tell my ex I’m engaged without reopening the wound. He’s a great guy. How do I break it to him gently?

A: There is no way to be gentle here, but you can be kind. He will be hurt. You cannot be the person who helps him with that hurt, because you are the person who hurt him. Tell him that you’re engaged, that you know it might be painful for him, and that you wanted him to hear it from you. It’s going to hurt him. Of course it’s going to hurt him. He thought you never wanted to get married, but you just didn’t want to marry him. There is no way around that painful truth. Don’t try to comfort him or manage his feelings. All you can do is tell him the truth and then back off. It may or may not end your current friendship—that all depends on how strongly he still feels about you.

Q. Re: Business travel and companions? The letter writer’s boss is not paying for his or her hotel for extra days out of the goodness of his or her heart. The company is doing it because cheaper airfares on the day the letter writer is flying outweigh the extra hotel costs. If that’s not the case, then the extra days are personal, with no business reason, and the extra cost is taxable to the letter writer.

A: A good point.

Q. Office phone etiquette: I work for a small nonprofit in a tiny office and spend a lot of time on the phone. My boss sits within earshot and apparently listens to phone conversations. Worse, he comments on them, yelling out across the office and forcing employees to ask the person on the line to hold on so we can listen and answer. Often the comments are not even pertinent because he can only hear one end of the conversation. Many clients complain and find it rude, but we feel we have no choice because he’s the boss. He’s supersensitive, has no one above him (or HR department), and we fear if we bring up this issue he’ll just turn it around and criticize us for not saying exactly what he wants us to say on the phone. What do we do?

A: This is (as you know) an incredibly tricky situation. Workplace conflict is always fraught, even when it’s not your boss who’s the problem. You can’t go over his head, you can’t go to HR for help, and you have to manage his hypersensitive feelings. I think the best way to try to address this issue with him is to phrase it as a physical difficulty, rather than a complaint about his behavior. Tell your boss, “I’m happy to discuss how you’d like me to handle certain types of calls. When you offer suggestions while I’m still on the phone, I have a hard time hearing and can’t offer the customer my full attention. Could we set up a time for you to offer suggestions once I’m off the phone and able to focus on what you’re saying?”

There’s an excellent chance that no matter how carefully you phrase your request he’ll overreact and then go back to yelling at you across the room every time you take a call. Have the conversation, by all means, but also start looking for another job—preferably one at a company with an HR department.

Q. Re: Business travel and companions? Generally everywhere I’ve worked it’s fine to bring a companion along on a business trip, as long as there’s no added expenses. Lots of old-school conventions even have spouse activities planned during the days. However, I wouldn’t mention that it’s to relieve anxiety. There’s nothing wrong with having a friend along for companionship, but I wouldn’t want to tell my employer that I’m not comfortable doing part of my job (traveling) alone.

A: I don’t think anxiety is something to hide or be ashamed of in general, but you’re right that she should protect herself by not mentioning her travel-related anxiety to her boss so early on in her tenure, unless it’s in the case of a diagnosed condition she needs ADA support for.

Q. Can I take back our engagement announcement? My fiancé and I have been dating for six years, have lived and traveled all over the world together, and have settled in my home country for now. We’re still struggling to find stable careers and a place to call home long term. Six months ago, he proposed, and I said of course—our engagement was no surprise to anyone. We announced right away that a wedding would still be a year or two in the future and that we want to host it somewhere that will allow our dearest (who are spread across the globe) to attend. The crappy economy and complicated logistics among our family and friends have made planning the wedding a low priority, down the list after our recent move to a new city far from our last home, looking for new jobs, and traveling to see far-flung family.

Since announcing our engagement, our wedding (for which we’ve only planned the playlist) is the first thing everyone asks us about, and it annoys us both. We’ve discussed eloping, not because we want to but to shut everyone up. The pressure to set a date has taken all the fun out of being engaged. We are practical people, and want to choose how to spend our limited time and money over the next few years without defaulting to splurging on a wedding just to appease people. I’m starting to wish we’d never shared our engagement, not because I don’t want to marry my fiancé, but because I’m sick of having so much pressure to throw the damn party. Can’t people just be happy for us and keep their mouths shut until they receive an invitation?

A: I don’t think your friends and family realize how much their innocent questions are weighing on you and your fiancé. If the idea of having a wedding is enormously stressful for the two of you, and you have no plans to host one in the near future, just tell them: “We’re engaged, but between our recent move and the economic downturn, we don’t plan on getting married anytime soon. We’ll be sure to let you know if that changes. What’s new with you?”

Q. Does she want to be my friend?
I have a friend “Jessica” I feel I have always been trying to get closer with, but I cannot figure out if she really wants to be friends with me. I am always texting and asking her to get together, and while she normally says yes, she never reciprocates. I see pictures on Facebook of parties she has that I don’t get invited to, and the next time we get together she has a seemingly good reason for why not. I have wanted to talk to her about this for a while but am scared. Should I just give up? Or should I confront her with the attitude that I have nothing to lose?

A: I don’t think there’s a reason to confront someone who wants to stay casual friends. If the two of you had once been incredibly close and she had suddenly backed off, that would be one thing, but you never were. You like her more than she likes you. It sounds like this lopsided affection causes you a lot of distress, and you regularly question why she doesn’t invite you to every party she throws, which can’t be a lot of fun for her, either. If she doesn’t initiate getting together with you, take it easy with your own requests and spend more time pursuing friendships with people who like you as much as you like them.

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