Thank you for your thoughtful response and sharing those real-life stories. Yours is one of the best responses I have had to this. I think they illustrate my argument. The trans woman who is dating men only has to be so careful because of the gender labels of “men,” “women,” and “trans.” I explained my thinking on this in more detail in a follow-up article, https://medium.com/inserting-philosophy/how-about-we-just-get-rid-of-gender-labels-altogether-7190b234eeb7. If we remove the social demand that everyone needs to be pigeonholed into a narrowly defined gender, then we open up a space for people to be themselves and they are free to express that. Obviously, this person should be honest from the beginning of dating and not hide their gender, just like someone shouldn’t pretend to be 20 years younger or several times richer than they really are, but without the gender labels and related stereotypes the whole issue is not one of conformity to social demands but being honest about who one is.

Similar with the issue of gender dysphoria — a problem that exists only because of society’s gender labels and stereotypes. NO ONE’S gender is wrong. There may well be as many genders as there are people. When we stop saying there are only two (or three) genders, there is no longer a stigma around finding out what gender you are.

And of course, gender is not sex and vice versa. So I am not dismissing sex or gender, I am saying that it’s the social pressure to conform to narrow definitions of gender and the demand that gender coincide with anatomical sex cause problems, such as the ones you describe. :)