Asking too many questions can actually distance you from your listener. Think of how you react to people who ask a lot of questions, versus how you respond to individuals who demonstrate a sincere interest in you. A lot of this is in how the questions are asked: are they directive, or open-ended story elicitations?
Ask for a story, and allow your listener to think about him or herself – not about you, why you are asking the question, and what your preferred response might be. Allow your listener to be the hero.