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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.This question rocks whether you're new to a city or you've lived there for years."You get to talk about local places she likes, see what you have in common, bond over the people, culture, and why you moved to the area in the first place," Jones says.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.
You can see if your personalities and interests jive, too. "Obviously you'll get an insight on her temperament," Sullivan says.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.Ask what sports she's interested in, what teams she roots for, and if she played sports in college.Depending on her answer, you can see whether you're up for some healthy competition or standing behind the same teams. You'll also find out how much time she spends on the couch.