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.