How to Ask a Tough Question: Terry Gross

"What is the key to a riddle wrapped in a mystery inside an enigma?" Photograph by Will Ryan

Off the air, I’m prone to having the same kinds of uncomfortable conversations as everyone else. On air, it’s my job to ask my guests about the experiences that made them who they are. Sometimes that means asking questions likely to make them uncomfortable. When I interviewed Woody Allen, his marriage to Soon-Yi was off limits. But since his new movie was about the relationship between an older man and a young woman, I had to acknowledge the similarity without intruding on his privacy. So I said his viewers would probably be searching for clues about his marriage. He avoided the subject but said interesting things about how viewers’ assumptions about him are usually wrong. When he did stand-up, people thought he was an intellectual. He said he was actually the guy “in his T-shirt with a beer watching the baseball game at night at home on TV.” I wouldn’t dream of asking a question like this at a dinner party. — As told to Susan Berfield

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