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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.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.
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.Good: You can see if she has a tight bond with her parents or siblings. "The five people we're around the most, shape us the most; her relationship to any one of her closest friends and family members tell you a lot about her," Jones says Waiting to be seated at your table or for your waiter to arrive?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.You can gauge whether she's philanthropic, an outdoor buff with a killer bucket list, and everything in between."Learn about her culinary skills, what food she likes, if she's into healthy cooking, and has any favorite restaurants, Sullivan says.
It's also the perfect way to gauge whether her level of passion is compatible with yours, Jones says. Each of these explanations reveals something about her character.