“So, what do you do?” and “Where are you from?” aren’t exactly the most scintillating questions to ask on a date—nor do they actually give you any juicy information about the person sitting across from you. If you really want to know whether you’ve got good chemistry and long-term potential here, you need to probe harder than that. But what kind of questions do you ask? We asked three dating experts to help us dig through all the small talk to come up with five no-nonsense queries that reveal a lot more than they let on. Don’t worry; there are no right or wrong answers. “You’re not looking for your clone,” says Laurie Seale, author of The Questions to Ask Before You Jump into Bed. “You’re judging whether someone shares your values and goals to see whether that person would be a good long-term partner.” And if not — if his or her answers are so wacky and opposite of what you believe that you don’t think you’ll last through the next 50 minutes, never mind the next 50 years — then at least you’ve had an evening of interesting conversation!
Here, the questions to ask:
Question #1: “If your company gave one-year paid sabbaticals, what would you do for that year?”
Maybe he’d run off to a remote island in the Pacific; maybe she’d start her own business, or spend the days working in a soup kitchen. Whatever your date answers, “This is a very revealing question, and a perfect one to ask on a first date,” says Seale. “It reveals your date’s true passions and priorities, showing you whether he or she is selfless, selfish, or overly ambitious.” You’ll also learn what this person cares about but isn’t making time for right now. “Your follow-up question should be, ‘Are you doing anything like that right now?’” says Seale. “Obviously she can’t spend every day in the soup kitchen, but does she volunteer on weekends?” And who knows—maybe you’ll wind up bonding over your secret desire to track down rare African birds or start your own Klezmer band.
Question #2: “Will you share an embarrassing moment with me?”
Is she secure enough to laugh at the time she gave a huge work presentation with ketchup on her shirt? Can he share the embarrassment of falling on Rollerblades while trying to impress an ex? It’s not the actual activity that matters—you want to know whether your date can be vulnerable around you early on. “If your date admits to, say, trying out for American Idol and bombing big-time, at least you know she doesn’t take herself too seriously,” admits Diane Mapes, author of How to Date in a Post-Dating World. And remember: If someone’s willing to share his or her private failures, you need to be ready to share some of your most embarrassing moments as well. In fact, it’s probably best if you spill the beans first, and one easy way to do that is to say, “First dates make me kind of nervous, but I always remind myself it pales in comparison to the time I took a crack at being a soccer goalie—and caught two balls in the face!”
Question #3: “If your house were on fire, what’s the one thing you’d make sure to save?”
Want to learn whether your date is sentimental or practical? Find out whether he’d rescue his grandfather’s pocket watch or his laptop, says Sharyn Wolf, author of So You Want to Get Married: Guerilla Tactics for Turning a Date into a Mate. “This question gives you a sense of what’s valuable to someone, and whether your values coincide,” she explains. Make sure to ask, “Why that particular item?” You may find she’d grab her college diaries because those were amazing years when she learned (and recorded) so much about life, or that he’d grab his vinyl record collection since he adores being a DJ at parties. And if you’re wondering how you bring up such an odd topic, consider an opener like, “I have a lot of interests and hobbies, but what’s truly close to my heart is fishing. In fact, my tackle box is the first thing I’d grab if my house were burning down. That, and my first edition of Jack London’s Call Of The Wild. How about you?”
Question #4: “What’s the biggest misperception people have about you?”
Maybe your date will say that everyone thinks he’s snobby and stuck-up, when he’s really just shy. It’s a good thing to know—especially if you’ve been sitting across from him thinking just that. “You’ll get a sense of how the person views him or herself,” explains Wolf. “And it gives you the chance to take a step back and rethink your opinion.” This is a great first-date question, particularly if you make the disclosure first, says Wolfe. Say, for example, “Sometimes people think I talk too much, but I just tend to babble when nervous. Is there anything you do that you think gives people an off-base first impression of you?” This gives you the opportunity to clear up any misperceptions your date might have about you, while also helping you know your “real” date without having to pry.
Question #5: “What’s the one life experience you want a do-over on?”
Here’s your chance to learn a juicy tidbit about your date’s past: Does he secretly wish he went to culinary school instead of law school? Does she rue the day she gave up her pet cat to clinch that great “no pets” apartment? Everyone’s got some regrets, and they speak tons about someone’s character. Not sure how to segue into this heavy question? You’re best off warming up first with your own confession, whether that’s how you wished you’d taken a year off after college just to travel or had quit a bad job before it became a really, really bad job. Just say, “I’ve been pretty happy with how things are going right now, but the one thing I always wished I’d done differently is _______. How about you?”
Brooklyn-based writer Amanda May has written for Redbook and other publications..
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