The question that makes someone comfortable is often more useful than the question that makes you sound interesting.

Questions are often used for display. The elaborate, clever one shows what the asker knows and leaves the other person working out how to answer it well. A plain question somebody can answer easily gets the conversation moving and tells you a great deal more. Making the other person comfortable is not a lesser skill but the one that actually produces conversation.

Ask something simple the next time you meet somebody new, and let your second question follow from their answer. Notice how much more you learn than when you were being interesting.