I thought she was a woman: My real-life crying game

Dear Really concerned and confused,

First, a couple definitions:

Cross-dressers are people who sometimes or always wear clothing and accessories traditionally sported by another gender — it's something they enjoy. Crossdressers usually identify as their biological sex, and many male crossdressers are heterosexual.

Transsexual folks feel their assigned or anatomical sex isn't the same as the gender and related roles they identify with. Some may undergo hormone therapy and/or surgery to cause biological and physical appearance changes.

Intersex people are born with an ambiguous biological sex. The old word for someone who is intersex is hermaphrodite, but intersex is now considered more respectful. People born with an intersex condition often have surgery as infants to assign them a sex, which may or may not agree with their gender identity.

Gender non-conforming or genderqueer individuals consider their gender identity to be outside the traditional male-female gender binary.

Transgender is used as an umbrella term for anyone whose gender identity or expression is different from the sex they were assigned at birth.

Keep in mind that not everyone will agree on these words and definitions, so it's best to use the term(s) (and pronouns) that people use for themselves. Also, gender identity is separate from sexual orientation. People who are transgender can be gay, straight, bisexual, or may not want to categorize their sexuality with a label.

Now, where did you meet these women? Was it at the same bar, or at different bars, in the same area of town? In some locales, crossdressers, transsexuals, and/or transgender people frequent certain clubs and restaurants. Maybe you've been unintentionally visiting queer bars? If this is the case, try hanging out at new places and/or asking around to find out if your future social destinations are known to host specific clientele.

Asking potential partners point-blank if they're packing a penis or vagina might turn them off. But hey, it sounds like it worked for you already. Such a question could show that you're a progressive guy who knows that the world is made up of all different kinds of people with varying interests, identities, and, yes,... genitalia.

It sounds like you were pretty upset at your discovery that your date's anatomy didn't match her outward presentation. It might seem a bit unfair for her to not give you any warning about what was going on, but you might want to think about things from her perspective. Transgender people face discrimination everywhere, and trying to explain the ins and outs of biology versus identity is tough on a first date. And, things may have gone faster than she had planned.

For those of you who're thinking, "This guy must be a moron," don't be so cocky. Lots of male-to-female crossdressers and transsexuals can pass as "bio-women" (as some trans folks call them). Crossdressers and other transgender people might also ask why their privates need to be made public; in other words, maybe your experiences are another reminder that we shouldn't make assumptions based on appearance and behavior.