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The State Media make some excellent videos for precisely this kind of thing. They have a video called The Dude's Guide To The Gender Debate which...

Marycate Delvey "Listen to Trans People!" https://www.youtube.com/watch?v=DVl-milXcCU https://www.youtube.com/watch?v=vcISDnHyCnE...

It might be helpful to introduce him to 'transphobic' trans people so he stops thinking all trans people think the same. For example, Buck Angel...

Honestly, have him start with page one of this thread. Enough of the toe-dipping. Plunge um into the water. Assuming this isn't a troll, I would...

Honestly just try Buck Angel. A lot of people aren't too fond of Buck here (Buck Angel is a female to male transitioner for 30 years) but also...

If he reads get him to read Abigail Shriers Irreversible Damage. Anyone who can read that and not come out despising the Gender Cult is a lost cause.