I think the first sympathetic portrayal I saw of a Transwoman was on Ally McBeal. Anyone remember her name? (I had a hard time just remembering Ally's name, lol...) One of the lawyers fell in love with her and even considered dating her after he found out she was trans, but he couldn't sustain the relationship.... and the show was about as honest as I've seen, portraying not just his reaction, but also her pain. I was amazed.
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