Just curious. I know that some women also do drag, but I have even less experience with that. So there's this guy I found online; he's single, gay, attractive, about my age, etc. But I am pretty sure he does drag sometimes, and I'm not familiar with that at all. I'm not saying I won't ask him out because he does drag, but I also don't know if he's the right fit for me. Any advice?
To answer the title question: Because they like it. Well, ask yourself if him doing drag is a problem. If it is, ask yourself why and work it out.
I think it connects with freedom to express yourself as you want to. For some it is about the act of feeling like someone else for a short while, others feel more comfortable in women's clothes and feel more attractive wearing makeup and for some a way to express femininity, a different side of themselves, it really depends on the person, but ultimately the act of cross-dressing is completely harmless and it should probably just be viewed playfully, gender roles and expression are anyway mostly socially constructed and viewing someone judgmentally according to gender norms is something that is considered fairly negative among the younger generation. Even though, I've obviously never been in a similar situation, it is probably good to give that person the benefit of the doubt and if you like him, get to know him and judge him according to his personality and emotional compatibility with you. If you think about it, admitting in public that you do drag indicates that the person in question is confident enough in their masculinity to admit it and they are open minded enough to experiment with different forms of expression, it also shows that they tend to be honest about themselves. All of these qualities are typically considered to be highly desirable in a partner.
I find it fascinating when men do drag (or when men do make up in general). Everyone's style is different and what people do with their ideas and expression amazes me. It's like why do people like working out? Probably cause it feels good.
