Bill is hilarious, and I love his comedy, but I think the point he is trying to make here is legit and perhaps lost.
I really think all he is saying is that for ignrorant people to understand anything, they cannot be approached with shaming and forceful acceptance. They have to be able to question, be heard, and then listen to explanation.
Bill feels like the situation with Caitlyn had no room to say, "Wait, what? What is going on? I don't get it." It was just "ACCEPT HER NOW OR FUCK YOU!" which gets you nowhere.