Do you ever ask trick questions to figure out if someone is a “yes” person? You know the type. They always agree with your point of view and repeat back to you what you just said without adding anything meaningful. Usually just to land a sale.
I’ve taken to asking questions or offering a wacky point of view in the middle of conversations like this just to see what happens (I only do this with new people, not old friends) and I’ve had some interesting results. Give it a try sometime.