and when he does you're going to do what you do as the le ebin fedora knight of the progressive society and point and laugh when he gets it wrong as you expect him to, because you've set it up in a way that there is no way you can possibly lose
He said "It's easy to tell them apart." I'm testing his ability to tell them apart so that he can see for himself whether that's actually true or not. It's not rigged, I chose both transgendered and non-transgendered individuals. I wasn't going to point and laugh, I wasn't going to act all superior or make fun of him. Like I said, it's not some sort of joke.
In some cases yes it's quite easy but just like "White men can't jump," it's just a generalization.