Context

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You'd like to have a meaningful, enjoyable conversation, most often with someone new, but maybe even with someone you've known for a while.

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Wonder Words

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"I've got a different idea of how we might get to know each other, if you don't mind. Let me explain. First I'll ask you a personal question. Then you'll ask me one. We'll go back and forth, taking turns. If either of us prefers not to answer a particular questions, we can smile and say 'no comment' and the other person comes up with a new questions. How would feel you about experimenting with this and see how it goes?"

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Example

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Jill: "I'm not sure what to ask. Why don't you go first?"

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Dwight: "Actually, if you don't mind, I have two questions together. What do you like about yourself? And what do you dislike about yourself."

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Jill: "Well, I like to play bridge, for one."

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Dwight: "Oh, I am happy to know that. But my question was 'What do you like about YOURSELF?' like I'm kind or I'm smart."

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Jill: "That's a harder one. Well, I've run into a lot of problems in my life but I always seem to get through them. I'm a survivor. Also, I like that I'm a helpful person. I help others whenever I can."

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Dwight: "In looking back over your life you notice how resilient you've been. And people are often grateful to you for your helpfulness, right.? Okay and the other question. What do you dislike about yourself?"

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...

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Dwight: "Okay, now it's your turn to ask me a personal question."

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Jill: "Hmmmmmm. Don't you feel lonely living by yourself and having no one to take care of you?"

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...

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See How to have a great conversation with anyone for an extensive list of personal questions.