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The April 21st episode of Real Time with Bill Maher talked about a number of trans issues with Rep Katie Porter and Piers Morgan. It was an absolutely brilliant episode that I recommend anyone watch. Maher is definitely left-wing, although he's certainly not woke.

That said, I have trouble finding any other examples of mainstream media discussing trans issues. The closest I've see are recent Dr Phil episodes.

https://www.youtube.com/watch?v=qTSE2C8E_5I&list=PLgCCULqQ1mqHbKMR7OgptTPgXUGR9dKmb

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Think that one was an older show with Kara Dansky. Think I'd seen a more recent one with Muslim reformer Asra Nomani.

Seem to recollect a segment from the latter of an exchange between a man and a transman over who gets to call themselves a man. But neither of them said exactly what they think qualifies a person as such. The guy apparently thought that the word means an "adult human male" while the transman apparently thought it meant "anyone who has any sort of a passing resemblance to an adult human male". Entirely different kettles of fish; with such contradictory definitions it's little wonder there's so little progress on the issue.

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The Dr Phil episode is from about 2 weeks ago. I wouldn't call that "old."

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🙄 Relatively speaking. If it will make you happy I suppose I might edit my comment to say "older" ...

In fact, I did say "older".

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