My boyfriend started crossdressing as a woman. Does that mean he's gay?

Hi, my boyfriend started crossdressing as a woman does that mean his gay? I’ve always noticed that he did it security (or so he thought) with my clothes and shoes but I never said anything. He is starting to do it more openly especially when he is drunk or on drugs. We have 2 kids and have been together for almost 10 years. Was our relationship a cover up? How do I start a conversation with him?

Béatrice (elle/she/her)

Hello Cheli!


First, I’d like to thank you for trusting us with your question. I know how hard it can be to reach out, especially with such personnel, intimate matters. Hopefully I’ll be able to help you. 

From what I understand, you’ve started noticing that your boyfriend sometimes puts on your shoes and clothes. You are also wondering if the fact that he puts on women’s clothes means he might be gay and you’re not sure how to address this with him. I also sense that you worry your relationship has been inauthentic or a way for him to cover up his sexuality. I understand how that might bring up different emotions, especially since you have a family and have been together for a long time. It’s completely normal for you to feel this way and I’ll try to help you navigate this complex situation.

First, I would just like to clear up the difference between gender identity, gender expression and sexual orientation. Gender identity is how a person feels they are inside, it’s the gender, or genders they identify with. For example, I identify as a woman. Gender expression is about the outside characteristics, like clothes, accessories, haircut, that we associate with masculinity or femininity. For example, in our society, we generally associate dresses, skirts, makeup and long hair with femininity. Sexual orientation is different from gender, it’s about who you are attracted to, sexually and/or romantically. A person’s gender identity and expression has nothing to do with their sexual orientation. In your boyfriend’s case, I want to reassure you that just because he sometimes wears feminine clothing does not mean he is gay. However, I completely understand your question because it is a common misconception. In our society, we often assume that because someone exhibits gender non-conforming behavior, it automatically means they aren’t straight. One of the many stereotypes that exists about gay men is that they are effeminate, but that’s not true. Gay people are diverse and express their genders in diverse ways. 

Then, concerning your worries about the relationship and your desire to talk to him about this situation, I would say that it’s hard for me to assess, because I don’t know him and I don’t know your relationship. You’re the expert here and my suggestion would be to have a conversation with him. I understand that this can be difficult, so here are some tips:

  • Don’t rush into it. It’s okay to take time to think about how you want to bring this up, when you’re ready to do so, and what exactly you want to say to him. It might even be helpful to write something down and practice what you want to say. You might also want to do research or talk to other people before you bring it up to him. Do whatever feels right.
  • Find the right time and place. Maybe this means making sure the kids are somewhere else, so you can take time alone. What is a place where you would both feel comfortable? What time would be best to have this conversation? Not only in terms of scheduling, but also emotional availability. It’s important that you’re in the right mindset to say what you want to say and that he’s in the right mindset to listen.
  • Stay away from judgement and accusations. Remember that it’s normal to explore and experiment with your gender expression, so he hasn’t done anything wrong. Maybe this is something he’s been thinking about for a long time as well. I understand that this might be very hard for you and that you may even feel betrayed, but I would suggest you avoid jumping to conclusions without having the full story. This should be a conversation between partners, not an interrogation. Remember to stay as open-minded as possible.
  • Have compassion for him, but also for yourself. This is a difficult thing you’re going through, but it might just make you stronger as a couple and make you see and understand each other in a new way. Take time for yourself, to sort through your emotions and think about your relationship. It’s normal to feel confused, angry, sad, hurt or anything at all. Is there anyone you trust that you could talk to about this? Maybe a family member or friend you might be able to lean on in this difficult time. 
  • Reach out. If you’re hesitant to talk to people you know, sometimes it can be helpful to talk to strangers who know what you’re going through. Writing to us was a step in the right direction. Here are some more resources in your area, either for now, or for later.

PFLAG is an organization that supports LGBTQ+ people and their loved ones. People who have been through experiences similar to yours. They have chapters all over the United States, including Chicago. Go on their website to find a chapter near you. 

The List is a collection of resources specific to Chicago.

This might end with one conversation, but it also might be the beginning of a longer process. I would say that these tips apply either way; take your time, communicate with each other, have compassion for yourself and your boyfriend, support each other, seek out information and resources when necessary. You are not alone, there are people who can help and support you. 


Don’t hesitate to reach out to us again if you have any questions or you’re in need of more support.

I wish you all the best

Béatrice (she/her), volunteer for AlterHéros