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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.

Everyone loves to laugh, and talking about the things that make you both fall into a fit—cheesy pickup lines, dad jokes, a particular You Tube flick—gets the conversation flowing... Lots of laughter on a first date is a great sign, Jones says.

This conversation starter can bring a light, playful, untethered feeling into your mix of questions, Jones says.

Better yet: "Many second date ideas can be born from this question." If you want the conversation to become a bit reflective, thoughtful, and meaningful, this is a great fall-back.

"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 is a great question to see how flexible she is," Sullivan explains.

You can see if your personalities and interests jive, too. "Obviously you'll get an insight on her temperament," Sullivan says.

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"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 sports are big in your life, this will take you into a ton of subtopics," Sullivan says.

And if she doesn't care, then you can decide whether it's a slight turn off or a deal breaker. If you're going to be compatible with a woman, you need to have common habits and hobbies. From this, you get a sense of whether she enjoys relaxing or letting loose when she's away from work.

Her interests are reflected in what she likes to watch on a daily basis. Is she on the road to self-improvement and solely reads to better herself and her career, or does she read for pleasure? "This is a good way to know what her intellectual interests and passions are," Sullivan says "Instead of asking how close she is with her family, ask: 'Who's the most influential person in your life? "This will tell you more about her family dynamics and close relationships she has with friends." Unless she moved around a lot as a kid (this should spark questions, too), asking whether she still talks to friends from childhood will reveal how she values relationships and loyalty.

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