Every morning during my work commute, I end up at a bus loop at around 8:20am. As I hop off my bus en route to the skytrain, I almost always walk past a long bus line-up. And standing in this line-up almost every time is a guy wearing women’s clothing.

Now, I’ve been around the block so to speak. I’ve partied with some transgendered folks in my youth. I’ve hung out with guys who like to dress up (quite expertly I might add) and entertain the crowds while dressed as Janet Jackson, Cher, etc. In other words, if a man wants to put on women’s clothing I’m 100% okay with that. But the cross-dressing morning commuter whom I see almost every day kind of makes me give my head a scratch.

For starters, he is wearing women’s business clothing but that’s where the efforts stop. His hair is somewhat feminine but not really (it kind of looks like a quasi-femmy bowl cut). Also his facial features are pretty masculine and he doesn’t opt for any real make-up, just some bright lipstick. And finally I can’t help but notice his posture. He is always slouching and his stance is not lady-like at all.

And he always looks a tad miserable. Or at least ultra-serious. I don’t know. If you’re going to dress as a woman during rush hour, why not put a little more effort into it, and hit it out of the park so to speak? And why not have a little fun, and just smile a little? But then his attire leads me to believe that he’s on his way to work. And maybe, just maybe, he’s just like the 80-90% of people (I’m guessing at statistics here) who hate their jobs or commute. So he really could be just like the rest of the general public. Except for the fact that he likes to wear skirt suits and nylons.

Without analyzing the situation too much, I just wish him a little happiness.