how to ask and what to do with the answer The question is easy, the conversation after it isn't. Here's a guide on how to actually have it. ask Pick a moment without an audience or a time constraint, a walk, a drive, side-by-side rather than face-to-face. If they say "I'm fine" but you're not convinced, don't let it go: Try: "For real though, how are you actually going?" "I'm always here if you want to chat." Then go quiet, let them fill the silence. when they say “not really