I know how it is, man. I'm coming up on 6 months on T and while most people have finally made the consistent switch to male pronouns, one family member is still holding back. It's my aunt, and what's confusing is we're really close. We can sit and talk for hours. She says she supports me, that she sees how much happier I am... but the first pronoun out of her mouth in reference to me is NEVER "he." Even other people have told her that isn't cool, but she says it's a force of habit. Maybe that's true, but it's such bull->-bleeped-<- to hear it from someone I really like. Even my own mother, who took the news the hardest, is great about using male pronouns. I haven't heard a slip-up from her in more than a month. And she sees me unbound every day. I don't see what's making it more difficult for my aunt. Then I get paranoid and wonder if she's doing it on purpose to kind of undermine me... I really wish people could understand how important this is. And like you, I feel like a dick if I have to step in and keep correcting them. (My fears of this were justified early in transition when my mother reacted harshly and negatively to even gentle correcting.) People get defensive if they're corrected, and I don't want to instill that reaction into a family member. But hell, I get defensive when I'm mislabeled, so I guess it's only fair to fight back against it. Still... god, this is one of the hardest things to do. good luck.
