Do we ever really know what someone wants, or just what they're willing to say?

Since the funeral I've been replaying every conversation I ever had with him, and I keep landing on the times he said 'I'm fine' and I let it go. How do you tell the difference between someone who's fine and someone who's just finished asking for help? Asking because I'm tired of guessing, and I'd rather learn it now than at another graveside.