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I'm an extremely shy person and I hate to ask probing questions, but in some ways this can be an asset for a journalist. When the subject of an interview sees me obviously struggling with a question, when I fumble and apologize and tell them I don't mean to be rude, it can soften them up so that when I finally do ask the damn question, they're less likely to blow up at me.
At the very beginning of my career I interviewed Johnny Rotten, and I arrived with all of these weird, very personal questions that my editor had suggested. I asked him if he wears a toupee and I got into all this stuff about his homelife, and I was such a mess that he took pity on me and answered my questions instead of going into a big Johnny Rotten tantrum. I think he found my awkwardness disarming. I'm not saying this was a great interview, but it WAS more personally revealing than a lot of his other interviews. So, if you feel like a creep when you're asking a question, try being honest about it. If the person blows up at you, you can always grovel and tell them you're really sorry for being so pushy, but then come around ask the question again.
Remember, you can always edit your question so it sounds much more concise that it really was!
