cross-dressing is a part of modern counter-culture.

Dear V,

I met this super cute guy at orientation and we’ve been dating pretty much since the beginning of the semester. This past weekend I randomly met him on a bus on South Beach … as a CROSS-DRESSER!!! What the hell is a sweet girl like me doing getting involved with a cross-dresser??? We haven’t spoken since Saturday, and I don’t know how to approach this situation. I don’t even know which one of us is more embarrassed by this event.


Dear Reader,

Wow, what a spectacularly awkward way to figure out that your sort of boyfriend has a pretty exciting life behind the scenes. I am assuming that you are a freshman, and I am also assuming that you have never been exposed to any behaviors that are considered to be a part of the modern day “counter culture.” Basically, cross dressing can be classified as transgender behavior, a behavior that doesn’t follow the norms of one’s gender. This is, however, not to say that there is anything wrong with cross dressing (because there isn’t!) or that because one engages in the behavior, one also assumes a transgender identity; it would be very incorrect to automatically assume a direct correlation between cross dressing and one’s sexual orientation.

I do, however, think that it may be high time for you and this boy to have a very serious conversation about the future of your relationship. Considering that you seem to be very bothered by his behavior (and you have every right to feel the way that you do), I would only think it natural that you would, and do, and will have problems trusting this boy. While you are probably still in shock and disbelief about the incident and about this part of him that you had no idea even existed, skirting the issue and not talking about his cross dressing and your feelings towards it will do more harm than good. If you already know that you won’t be able to date a guy who cross dresses, and if you have a shred of civility within you, it wouldn’t be right to completely drop him without talking about the big white elephant in the room. Word to the wise – just because you don’t know that it’s happening, doesn’t mean that it’s not happening.

Best of Luck!