I'm right there with you, but I can't ever seem to thread the needle. Like in your Matrix example I have had people get offended by a question like that.

More generally speaking, I think it's so difficult because a lot of people aren't actually all that interested in learning or communicating in a way where a mutual understanding of each other's base reality/knowledge are understood. They prefer to operate on their innate or learned social cues and prefer making assumptions or reading between the lines of what the other person is saying. Or in modern parlance, they just go by the vibes.

I have watched two people completely talk past each other and misunderstand the other person and yet they both seemed to come out of the conversation pleased with the interaction so many times. It's baffling to me.