I am an older trans female and even though I have a male size body I can pass as female when dressed and with makeup on. So to the casual observer I am female. Due to work constraints I have not done my gender marker change yet and so when I have to present my identification it becomes an obvious subject and I have to explain. I look nothing like my driver’s license photo. But if a person I meet does not know my former life then I am not going to tell them I lived in a male body. I will only tell someone that needed to know.
Would I tell a potential date? Yes I would if I had not physically transitioned. I think that a lot of the young trans girls that get hurt when dating did not reveal this information when they started and the guy became angry and enraged when they found out.