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13-Oct-2017 18:02

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.

"You get a glimpse into her day, her job responsibilities, how she deals with stress, her energy level, tone, and how she spends her time," Jones says. Some say you never truly know someone until you travel with them.

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.

But you'll also be able to reign in any bad habits that might prevent you from nabbing a second date.

"Her answer will reveal whether she has a dark, goofy, nerdy, romantic, sappy, or quirky side," 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.

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Break the ice with a simple, straight-forward question like this. All these alternatives offer "insight into her lifestyle, taste, and knowledge about other cultures." Sullivan says.This question rocks whether you're new to a city or you've lived there for years.