Dear Prudence

My Boyfriend Has Started Dressing as a Woman, and I’m Not Attracted to Him Anymore

Prudie offers advice on shifting relationships and friends with food issues.

Woman looking sad in front of a cross-dressing man.
Photo illustration by Slate. Photos by monkeybusinessimages/iStock/Getty Images Plus and Discovod/iStock/Getty Images Plus.

Welcome to the newest addition to the Dear Prudence lineup: the Friday mini-column. At the end of the workweek, Prudie will answer two more questions from the mailbag. This week: shifting relationships and friends with food issues.

To get advice from Prudie, send questions for publication to (Questions may be edited.) Join the live chat every Monday at noon. Submit your questions and comments here before or during the live discussion. Or call the Dear Prudence podcast voicemail at 401-371-DEAR (3327) to hear your question answered on a future episode of the show.

Dear Prudence,
I am a cis woman in my mid-50s who’s been in a really nice relationship for about five years with a man my age. He grew up in a very stifling, fundamentalist family and later became the father in a similar family. When we met, he was recently divorced and beginning to discover the rest of the world. We have had a terrific five years, filled with exploration and honesty, and it has been refreshing. I genuinely love him. Recently, he has expressed his wish to begin dressing as a woman. Apparently this has been a long-buried interest that he felt unable to explore; I am very happy for him. We’ve shopped for clothes, laughed about the ridiculousness of makeup and heels, and found some venues where he feels comfortable going out all dressed up. The problem is that while this whole process seems to have made him feel even more committed to our relationship, it has not had the same effect for me, at least not in the romantic sense. I’m really not attracted to his female persona. Even when he’s not in drag, I’m not feeling the physical passion that I once did. I feel so guilty! I want to support him, but at the same time I feel I’m being dishonest when I try to respond to him sexually. He is truly my dearest friend and has been an amazing lover, but I feel that if I try to back off our relationship to friendship, he’ll experience it as a rebuke of all he’s worked hard to become. How do I continue to support his growth without compromising our friendship or my own happiness, which may not include a physical relationship with him?
—No Femme on Femme

Your soon-to-be ex may very well take this as a rebuke, or at least a very sad coincidence, because it’s unfortunately the truth—the very thing that’s making him feel free and excited and hopeful for the future and closer to you is turning you off and causing you to look for the nearest exit. That’s the truth of the situation, so don’t go into this breakup thinking you can somehow avoid causing him pain. I think it’s clear that this is likely to become a bigger part of his life, not a smaller one, and since you already know that’s not what you’re looking for in a romantic partnership, you have sufficient information to end things now. But while it’s sad that you two have reached a point of mutual incompatibility, it’s not something you can blame yourself or take responsibility for, and you certainly shouldn’t be pressuring yourself to respond to him sexually when you’ve lost all interest. Supporting someone and continuing to have sex with him when you don’t really want to are not the same thing! You can assure him that you’ve enjoyed the last five years immensely and that you hope very much you can continue to be a friend to him whenever he feels ready, then give him (and yourself) space to mourn the end of your romantic relationship.

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Dear Prudence,
How do I handle my best friend of many years constantly pushing food on me? She is an incredibly generous person with really high energy. She packs a lot into every day and has always been there for me. She also eats constantly because she has low blood sugar and gets lightheaded if she doesn’t. Lately she has become increasingly insistent that I eat with her too. But I don’t want or need to! We went for a bike ride together the other day and had only ridden for 10 minutes when she wanted us both to stop and have a snack. She repeated this a number of times and each time pressured me to have food too. I really am fine with her eating whenever she likes, but I’m struggling to get her to accept my “no.” We have both put on weight over the years, and I am trying to eat healthily and exercise more. To be clear, I can (and do!) say no, but what I really want is for her to stop pressuring me. What do you suggest?
—Quit Feeding Me

It’s not unheard-of for people to take their friends’ sudden changes in diet personally, and I wouldn’t be shocked if your friend’s increased suggestions that you two stop and have a snack coincided directly with your attempts to change your own eating habits. That doesn’t mean you should accuse her of doing anything on purpose (especially since it may be subconscious on her part). But since she has a habit of not listening to your “no” the first time, your next step is to bring the issue up before she does it again: “I’ve noticed lately that you’ve been offering me food more and more frequently, and when I tell you no, you don’t back off. It’s happening regularly enough that I’m starting to feel frustrated. I don’t try to tell you when you should or shouldn’t eat, and I wish you’d do the same for me. I want to be able to go for a bike ride or see a movie without worrying about how I’m going to convince you that I’ll eat when I’m hungry. Can you knock it off, please?” You don’t have to explain to her that you’re trying to change your eating habits or have specific weight loss goals. You have every reason to ask her to respect you when you say no without having to justify it with a diet and exercise plan.

Catch up on this week’s Prudie.