Okay so I need advice. I'm trans and every relationship I've been in was during the time I was closeted. I worry about getting back in the 'dating game' so many years later, because I'm stealth and (I've been told) I pass flawlessly. Right now I'm interested in a cis gay guy, who doesn't know I'm trans. What do I do? What is the best time to bring that up? I don't know his stance on dating based on sex or based on gender, and I don't know a not-awkward way to ask that.
WELL this is a really good question that i wish i had a good answer to.
however!!! honestly my best advice would be to shift the issue in question off of yourself and introduce it to him like that. so instead of starting off by saying youre trans you could start off by talking about a “trans friend” that you have or someone you supposedly know who is dating/thinking of dating a trans person and you could talk to him about his opinions on that. and then youll have a better idea of how he would react.
i know that might sound weird and complex but i think its safer and generally less awkward to introduce a scenario to the conversation before you disclose personal info that might create a bad situation for you.










