Regarding "liking woman a lot", I was quoting the original author - it seemed like an autogynophilic statement to me, the idea that you are sexually attracted to something so much you want to become it. Maybe I'm misunderstanding!
Yeah it's interesting what you say about Blanchard... the fascinating thing for me about Blanchard is the measurement of groin blood pressure to test for arousal in response (rather than relying on self-reporting), I think his solutions were sexist and backwards and a great example of how blinkered medical professionals can be.
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If we expand the dictionary definition of woman to include some men, we then need a new term to describe... well, actual women. I know a lot of people want to adopt the term "cis woman" for this, but I'm going to stick with "woman". If this is just my personal aesthetic judgement that's fine, the burden of proof is on others to expand it and I don't think the justifications are very good.
Regarding the actress you mentioned, Brian, I can totally see I might mistake her for a man as she's gone out of her way to masculinise her appearance. I wouldn't feel guilt if I used male pronouns then later realised that was incorrect (according to my own rules) - perhaps surprise? I wouldn't even feel temporary embarrassment because she's gone to lengths to look male. I would correct myself to use she/her - even in direct conversation. That might be awkward but it's fine.
If I was in a country, organisation or situation where my livelihood was at risk for using sexed pronouns, I would avoid using pronouns entirely as regrettable prudence. This isn't hypothetical: parts of my social life overlap with these kinds of people and I steer through it, often by saying less, but I won't lie to someone directly.
I don't feel guilty about saying I don't believe in god/heaven to a catholic priest, even if the logical implication is that, from my perspective, they've wasted their life and chances of a happy love and sex life. It's unfortunate but really has nothing to do with me, it's all based on a set of attitudes and beliefs I don't participate in (and personally find regressive).