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Catching her off guard is a good thing so long as your intentions are innocent and playful.Despite the quirkiness of this question, you'll find out what's most valuable to her and the significance of those items Light-hearted questions like this one can stir up memories from her childhood. It may seem silly, but if she hates dogs and your Husky is part of the family, or she's got two cats and you're allergic, things might not work out. You'll find out if she's been running with bulls or scaled a mountain.If there's one thing that can ruin a first date and ensure a woman's first impression of you is a bad one, it's crappy conversation.

"Not only do you get to hear about her life story, but the snippet that's most meaningful and important to her," Jones explains.This may seem a bit odd and specific, but how she likes to travel is sometimes even more telling than where she likes to travel. "This opens the door for conversation relating to history, religious perspectives, art, and culture," Sullivan says.If she's crazy about museums and monuments, you can infer she's a history buff—or better yet, ask her if she's a history buff. You'll get major insight on her goals and priorities in life.Meet the experts: Sarah Jones is a relationship expert, and founder and CEO of coaching website Introverted Alpha, and Sameera Sullivan is the CEO of Lasting Connections, an elite matchmaking service. "This is a great ice-breaker because it's a little mischievous and flirtatious," Jones says."It's a sign you'd like to know her beyond surface level, while still giving her the freedom to reveal what she wants to share—and doesn't." This question lets you get a sense of what she feels strongly about and whether she's spirited and heartfelt.

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