After coming out to family (fear of rejection) and coming out at work (feat of discrimination), I think my personal worst is coming out to exes, because I never know how threatened they'd feel in their sexuality and how that would manifest. Specifically, if they'd become violent.

Case in point, the guy from yesterday felt so insecure that he found it necessary to show up at my mom's place at 11 pm last night to call me outside, and then to proceed to shout for the whole neighborhood to hear that I'm a woman, I'm nothing but a woman and that my transition might *feel* like it's important to me but actually *he's* the one who's truly affected by it, because it makes him gay and he's totally not gay and how dare I undermine his masculinity like that...  Which are totally valid feelings but there's a good way to process them and a shitty way to process them, and this was the latter. And I love this dude to death, he's still a really good friend, but he also has abusive tendencies, which both me and other of his previous partners have been subjected to... If he reacts in such a volatile way, then I don't know just how violent others might get.

Not that I make a point of coming out to every dude I've ever dated. However, I'm on friendly/speaking terms with a number of them, we keep in contact, and these things come out.