If you have ever watched or listened to interviews on TV or radio...
The best and most insightful interviews are those where the interviewer asks a question, listens attentively to the answer, and then asks follow-up questions based on the particular response. Be ready to throw out your "list of questions" if the conversation leads in an entirely different direction. A perfectly great interview/date can be ruined by lack of listening and simply following a "list of questions".
The old Beatles song (originally Buck Owens) sums it up: "Act Naturally."