Some how my co-worker got me to open up about my ex-wife and ex-girlfriend. I try not to invoke their memory, but when prompted, I may never shut up about them. There’s something humiliating about being cheated on. You begin to wonder if you are not enough of a man to satisfy them. That leads to questioning everything from personality to height to um…other sensitive questions.

Logically, I know it’s them. Isn’t it? I’m the common denominator, so it’s natural to assume that maybe I’m the problem. Am I? My friends seem to think that I’m not to blame. There seems to be a pervasive sense of self-entitlement in our society. People want to feel good at all costs, even if that means humiliating and demoralizing the person they promised to love and be faithful to.

I can’t but wonder how much better my life would have been had I been born the opposite sex. I’m not an aggressive person. I’m tend to be passive, which is not to say that I enjoy being submissive. I don’t. I want – no, I need – to be in control of my own life. I don’t want my life’s choices being dictated by another, but I tend to be more of a go-with-the-flow personality. Rarely do I initiate conversation with people. Less often do I ask someone out on a date.

But being another sex and/or gender wouldn’t solve anything. I would simply be trading one set of problems for another. Maybe that’s why I love to dress up as a woman. Maybe I want to flee my life of mediocrity and self-loathing by becoming someone else. Someone so unlike myself.

It’s just a thought. Regardless, I try not to get down on myself about being in my late thirties, single, with no prospects of ever being in a relationship again. I fail, but the point is I try.