I am in a complicated position and don't know what to do. I like my men as feminine as my women. The few men I have dated have been very gay and I am just attracted to that kind of guy. The people I have dated though just kind of knew I was trans from being in our group. I have never had to tell someone. I am still pretty quite about my private life so if you don't already know or ask about it I will keep it to myself. Recently though, a guy I knew from middle school thru high school, has been hanging out with me. He is pretty in a masculine way. Not someone I would typically go after but still attractive in a straight way. He knows I am 'female' but likes my 'tomboy' look. He said I am the only 'girl' that likes the same things he does. That none of his ex's shared the same interests. We get along very well and I am rely attracted to his personality. Recently though, he has been dropping hints that he wants to go out. Or at least change our title from friends to dating. I don't want to get involved until I tell him I am trans otherwise it will feel like I am lying. I will also be on T soon which is going to bring up questions if I keep quite. I also am always the dominant one. I have never been with a straight guy. I am sure that may cause problems and don't know how to bring up our roles if we were to go out. I know this should be something we discuss before hand but it is not rely everyday conversation and it is pretty awkward. I have brought up stories of trans people. I have given hints I am trans. We were watching something the other day and he said that he believes the soul is more important than gender and it would not stop him from loving the right person. I still am finding it very hard to tell him straight out and make sure there is no assumptions. I can never get a conversation going that direction or even what to say when it does go there.
Hello, You could either tell him at the end of the date so if he doesn't like it or you decide you don't like him then you can just leave and never return, or if you like him and suggestions say he still might like you then you could do it at the beginning of the next date and say that you can answer any questions he might have. You could always say ''how would you feel if you were in a homosexual relationship?'' [if you don't know already, and then you can know how he'd feel in the relationship rather than you as an individual].
Ok. He is straight? That would mean if you start dating, he would be dating a male. You need to tell him before the date, not after. If he's not straight, not an issue. He's either bi, or gay and either way, not an issue. Although, soul more important then gender? I don't think it will be an issue.
Maybe he already knows? You said you never had to tell anyone else, and that you've dropped hints; his comments about liking tom boys and soul being more important than gender could be his hints to you. Good luck!
That he dropped that "soul is more important than gender" line to you makes me think perhaps he can tell/thinks that you're a boy, and could be his way of opening that door to say hey I'm cool with this. In any case, I'd definitely make it clear to him that you're a guy before asking him on a date. If he likes you that much and was serious about gender not being as important as other things, it will probably go favorably. Good luck!
I think it's important that you tell him before you date or go out with him, mainly so he doesn't feel like you were hiding it from him. He may not mind at all, as he implied with his "soul is more important than gender" comment, but even if he doesn't mind, it might make him upset if you wait to tell him for too long.
