Funny you should post this ... I was watching that Calpernia Adams video about Bad Questions To Ask A Transsexual and altho' a lot of it was very funny, I also found it kind of aggressive and intolerant to people who are often only trying to say the right thing.
I've had lots of 'brave' remarks, but the only time people have said they were glad is meaning that they were happy for me that I was doing what felt right and true to me ... so that was supportive. i guess in general, I ask myself two questions ...
1. What is this person's intention? If they're obviously trying to say something nice, kind or appropriate, but they get it 'wrong', I don't see that it's fair to be offended. I mean, how are people supposed to know what is or is not the correct way to talk to someone who is going through or has been through transition? God knows, we all fight about it amongst ourselves: just look at how easily some people get p*ssed-off on TS messageboards at what other girls have said to or about them. So if someone has a good heart, that matters more to me than their specific words. And if they don't have good intentions, why then they can just ->-bleeped-<- off out of my life, can't they?? *she smiled, sweetly*
2. What is this person's relationship to me? If someone I don't know starts opinionating about me, well, that's risky for them, because they haven't really earned the right to make a judgement. Friends and close professional colleagues have a lot more leeway because of the trust we've hopefully built up over the years. My parents, sisters, wife and children have a total right to say what they like - particularly my wife and children. I am potentially screwing up their lives. I'm taking away the face and body of the husband/father they love, and that's a kind of bereavement. I'm breaking, or at the very least threatening my marriage vows and the unspoken promise you make as a father to your children. That's not to say I love them any less, nor that I can't still be a loving part of their lives. But at the very least it's a helluva shock. And if I'm asking them to cope with my transition, then they have a right to ask me to cope with anything they feel like saying to me.