I know your type and it's great! But yes, a connection is a dance, so if I'm getting pelted with these seemingly reasonable questions (read: "and how did that make you feel?"), they start feeling insincere.
I can't tell you how many people I know who must have read "How to Win Friends and Influence People" once and became parrots whose only contribution to the conversation was to ask me questions and say my name repeatedly. That does not make a good conversationalist.
