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What was the last thing you learned that made a big impact on you or an ah-ha moment? On a scale of one to ten, how happy are you? Do your thoughts on monogamy, behavior at parties, flirting, and business trips coincide? This also gives them and you a chance to talk about previous vacations, expanding the conversation. Where is your favorite travel get-away?

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This might be a very unoriginal question to ask, but it is a classic for a reason.

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18 First Date Questions From The Experts

If you could travel back to any one point in time what would it be? What is your guilty pleasure song? Some of these 21 questions to ask a boy range from the simple emotional to the blatantly sexual. How do you react? What's the best email address for our matchmaker to reach you? What was something that recently moved you?

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