And then what do you do if they say "no"? :)

Personally, I'm annoyed by people who say "you can ask me anything, go ahead" (especially in response to the "most private thing" prompt on OKC). It's a way of putting the burden of making conversation on the other person, instead of sharing it with them.

Meh... The more I think about it, the more I love prompting your interlocutor to gossip about a third person. You can potentially learn: -How interested she is in other people -How willing she is to talk about other people behind their backs -How much she knows about other people -What qualities she values in other people -Whether she tends to judge people generously or not plus whatever actual facts you may manage to glean about their relationship with said third party! It's great! It's kind of ethically shady, but I am drunk and willing to overlook that for the sake of argument.

Edit: Hey guys I fail at lists sorry