It’s been addressed numerous times before, but one might wonder “why would a transgender person not list up-front in 72-point font that they are transgender when dating?”
There are a few answers I can think of.
Foremost, some of us who have transitioned have simply moved on into our normal, everyday lives. If we have passing privilege, then even more so. It’s a medical condition. Should people also be putting foremost in their profiles “I’m a Type I diabetic” or “I have IBS?” Not every single date is a pathway to marriage - many dates are just that, and if you have a common interest with the person and you like them and you think they’re cute…why do you care so much about a transgender history for a simple date?
If the person is pre-op, then IMO YES, there needs to be some explanation prior to any sexual act. Mainly due to the fact that angry, cisgender men beating or murdering pre-op transgender women has almost become competitive sport for some. If they are post-op…why do you care? I can assure you, men cannot tell a natal vagina from a surgically crafted one (hell, they can’t even find the clitoris half the time). I’ve seen LOTS of cisgender and transgender vaginas very up-close and personal, and no I’m not telling any stories. Women can usually tell a crafted penis from a natal one, simply because the state-of-the-art in surgery is still not very good, but not all the time (and remember, Billy Tipton had no penis at all, yet his wives never really knew (or took years to find out)).
If the relationship begins to move toward permanence (as much as anything is permanent in relationships), then there needs to be a talk about how a past life could come forward, about the inability to bear children/father children, etc.
Ultimately, the concern over genitals is often “trans panic” by incredibly fragile homophobic men who believe even thinking a transgender woman is attractive means they are gayer than a $3 bill in the pocket of a Miami Beach doggie hair stylist.
There is a lot of debate in my community over informing versus not. There are many young firebrands who believe that you never need to tell, ever, under any circumstances. I on the other hand believe telling as early as possible is best, because you want to find out if you’re dating a bigot, or dating someone who is interested in more than you can offer them, and because I personally have friends right here in my city who bear the scars of being beaten by angry, cisgender men at the end of a date. My position seems to be a minority one.
Another aspect of those who do not inform is, well, loneliness. Advertising that you’re transgender on a dating site typically lands you chasers (many creepy), hetero couples who are “curious” about a threesome, or other transgender people. As the months and years pass, some of us just want to have any human contact, so we will not mention our past, and hope against all hope that the person we have a first date is kind. But it’s like being in a ticking trap - the further the relationship goes, the more there is to lose when you do come out. The more fear and uncertainty and dread. It can be worse than never having tried. I know people who didn’t tell until the 5th, 7th, 10th date, sometimes even years into the relationship. It almost always ends in tears (the only time it didn’t is when the partner figured it all out very early on, and respectfully never brought it up themselves.)
When I met Fierra on the SDMB, she knew I was trans before our first date - I told her when she asked me out. Her reaction: “Oh cool! Do you like Indian food?”