Dear Rabbi Simon
Is it permissible for Jewish men to date or marry transgender women?
Thank you for your contemporary question.
The phenomenon of gender dysphoria and its many implications is increasingly widespread, and the possibilities for pharmaceutical and surgical intervention leading to transsexualism have advanced dramatically in recent years. This, of course, is the background to your question.
The Jewish view of the subject, however, remains conservative. Medical intervention does not alter the halachic status of a person as either male or female. (Although the halakhah recognises the phenomenon of androgyny, this is not the same as a male deciding that nature has erred, assigning him the wrong body, and he should actually be a female.)
Turning directly to your question: For a man to befriend a transgender woman is not objectionable, but I would not encourage a man to “date” her in the conventional, romantic sense. It follows that marriage would, in Jewish terms, be invalid (as the transgender woman is halakhically a man) and marital relations would also be prohibited (for the same reason).
Regrettably, the possibilities for a transgender woman (or man) in terms of romantic companionship, love and marriage are rather constrained within the parameters of Jewish law. I should probably add that the process of changing one’s sex, particularly from male to female, is contrary to Jewish Law as well.
That is not to say, however, that such a person should be shunned, shamed or otherwise gratuitously mistreated. Every person is deserving of human dignity and respect, whatever personal choices that individual has made.
I hope this is helpful.
Rabbi Rashi Simon