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Those small details and what she chooses to focus on—whether good or bad—clue you in on her personality big time. Odds are you won't be traveling on a first date, but this question (paired with the above) can offer a ton of clues about her persona.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."Her answer will reveal whether she has a dark, goofy, nerdy, romantic, sappy, or quirky side," Sullivan says.Plus, you won't be blind-sided if you make a movie date and you're stuck sitting through a rom-com.Plus, they're backed by professionals who know what they're talking about. It promotes a good back-and-forth between the two of you.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.

This question rocks whether you're new to a city or you've lived there for years."Learn about her culinary skills, what food she likes, if she's into healthy cooking, and has any favorite restaurants, Sullivan says.Food is always a safe topic of conversation—and an endless one, too.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.You can gauge whether she's philanthropic, an outdoor buff with a killer bucket list, and everything in between.

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