I'm still really early in sorting through my gender issues. I'm still presenting as a male everywhere, even on this site. But I've had a lot of experience talking about it. What I found was that it has gone best when I could "prep" the person for it first.
So for instance, when I talked to my wife about it last year, I first said, "I have something that I really want to talk to you about later on. I'm not ready to talk about it yet, but I'm really afraid you're going to reject me. It's a pretty big deal. Can you commit beforehand that you'll stick with me and not reject me?" I found that that eased the way for me to talk about it with her.
Last week I had a similar conversation with my teenage daughter. After reading some comments on here about how people have been so terribly rejected by their families, especially at the holidays, I was really torn up. So I said to my daughter, "I'm going through some really difficult stuff right now. I can't really talk to you about it, because I don't want it to create more stress for you. And I don't really even know what I'm going through. But a lot of people who are going through what I'm feeling end up getting terribly rejected by their families. I just want to know... even if I end up not being the strong dad you think I am..."
"You're always strong, dad," she said.
"Yeah, I know it might seem that way to you. But I don't feel that way right now. Depending on what happens, I just want to know that you won't reject me." And I started crying.
She hugged me and said, "I could never reject you dad."
So my advice is to broach the subject first by asking him to reiterate that he would never reject his children. And then say that you're dealing with something really difficult, and really hard to talk about, and you're really concerned about how he'll react. And then if he's open, you can tell him then. Or if not, you can wait.
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