Here's one that happened in the early weeks of our separation:

Me: So, how are you doing?
H: I'm really happy and relaxed, actually.
Me: That's cool. (pause) So, what do you think you'll do if/when you start having some regrets or start feeling unhappy?
H: I couldn't be more depressed than this!

WTF?!

Thankfully, he's more clear now when he communicates, but those early days were a nightmare.