Dear Barb – Cross-dressing boyfriend

Dear Barb: My boyfriend and I have been together for five years. We get along great and I really thought he was the one for me. However, I just discovered a very disturbing thing about him. My boyfriend likes to dress up in women’s clothes. I find this very upsetting. Even though I love him, I don’t know if I can live with this behavior. My boyfriend says I’m making a big deal about nothing. He says he just likes the feel of women’s clothes. Why do men like to dress in women’s clothes? Could my boyfriend be gay? Should I continue in this relationship or am I just asking for problems?

Need help in Victoria!

Thanks for your letter. I’ll do my best to answer your questions.

What your boyfriend does is called “cross-dressing.” This term can be defined as, “the act of wearing the clothing of another gender for any reason” (Reference com). Simply put that’s all it is — choosing to wear the clothes of the opposite sex. There is no sexual implication involved. A person is not necessarily gay because they cross-dress, but they could be. In North America, the term cross-dresser is often interchangeable with the word transvestite. However, in some cultures the word transvestite is used to describe a male who feels like a female, but would never consider a sex change.

Most cross-dressers in western society are male. This may simply be because when women wear men’s clothing it is not necessarily seen as out of the ordinary. However, a man wearing feminine attire is definitely seen as odd or peculiar.

There could be a variety of reasons why your boyfriend is choosing to dress in female clothes. However, you and your boyfriend seem to have been able to maintain a relationship in spite of his cross-dressing. I get the sense from your letter that you are happy for the most part with this man. Have you considered speaking to a counselor about this issue? Perhaps you could see a counselor together. You may be able to discover if there is anything more complex going on, or simply that your boyfriend likes to dress in women’s clothes.

Although this behavior may be difficult to accept, if you want to maintain this relationship, you may have no choice but to accept it.

My suggestion is to carefully consider all your options before proceeding with this relationship. Don’t think you are going to get married and change him. This will only lead to stress and unhappiness. Most likely, your boyfriend will always dress in women’s clothing from time-to-time. Only you can decide if this relationship is fulfilling and positive for you.

E-mail your questions to Some submissions may be edited for length or to protect confidentiality: your real name and location will never be printed. This column is for entertainment only. The author is not a professional counsellor and this column is not intended to take the place of professional advice.