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When a first date feels more like an interrogation than the adorable banter portion of a rom-com, chemistry can fizzle faster than those perfect leggings disappear during a flash sample sale. And to keep the convo flowing as easily as you swipe right on pics with dogs (just me?), there are right and wrong questions to ask. But according to two relationship experts, their substance might surprise you.
“The common wisdom goes that you shouldn’t talk about politics, religion, or money on a first date. I disagree,” says Hannah Orenstein, a New York City-based former matchmaker and author of the forthcoming book Playing with Matches. “Those are major factors in how we live our lives. Instead of shying away from subjects that might be considered too controversial, I’d say go ahead. It’s better to find out if you’re incompatible sooner rather than later.”
But that doesn’t mean you should lead with “What’s your salary?” or “Who did you vote for?” The goal of the first date, as Orenstein indicates, is to get to know the other person, but you want to do so in a way that doesn’t make them feel put on the spot or like they’re interviewing for a position at your company. The best questions are therefore ones that get to the heart of important info (like the person’s passions and sense of humor) but are easy for them to answer. Need some examples? I’ve got you.
Bookmark these expert-approved Qs to ask (and avoid!) for your next first date, and it just might be your last.
Ask: What were you up to this weekend?
“If you ask a person about their hobbies, they’ll probably freeze up,” says Orenstein. Even if he goes to Barry’s Bootcamp every Sunday, runs half-marathons, or enjoys cooking adaptogenic recipes, he might not consider those “hobbies,” so if you frame the question the wrong way, you might amiss out on knowing that you could finally be one of those cute couples that run half-marathons together. “But if you ask about what your date did this past weekend, you’ll get the same information in a more casual way,” says Orenstein.
Don’t ask: What was your ex like?
“While this might be an important fact to discover, you definitely want to steer clear of any past relationship talk on the first date. The evening should be about you,” says Jonathan Bennett, co-founder of the Ohio-based relationship coaching company Double Trust Dating. “In fact, if all your date talks about is past relationships, it means he or she isn’t over them,” he adds. And it’s definitely not a great sign if it feels like they’re fishing for any reason to mention their ex, like, “Oh, my ex likes water too…” Pass.
Ask: Do you have any fun fall plans?
“On the surface, this gives you a general picture of how a person likes to spend their time,” says Orenstein. You might find out that they spend weekends hiking with friends or that they rented a house in the mountains during a long weekend. “But beyond that, it’s a subtle way to uncover any major life changes that are coming their way that could affect a potential relationship—like, if they’re planning to suddenly move to a different state,” she says.
Don’t ask: Are you having fun?
Don’t “kill the vibe” with this question, says Bennett. “If you think your date is bored or not interested, you should find a way to make the evening more appealing and fun.”
It should be clear, based on your date’s body language and the conversation, whether things are going well. If it seems like he or she isn’t having a great time, try not to take it too personally. You don’t know what’s going on behind the scenes (with their family, at work, etc), and it’s also possible you two just aren’t a good fit.
Ask: Do you like your job?
If you’ve been set up on a blind date, swiped right on an app, or met IRL, you probably already know what they do for a living. “This question goes a step further and gets at what your date really likes,” says Orenstein. “Maybe they’re just biding their time until they can drop everything and travel the world or run for office or write a novel.” You’ll find out what they are passionate about, which might not be their current 9 to 5.
Don’t ask: Are you dating anyone else?
Even if it’s unintentional, this question insinuates that you already want to be exclusive, and you definitely don’t want to seem clingy right off the bat. “Although you will need to know this if you get serious, on a first date, you have to assume that your date has other options,” says Bennett. “By asking this question, you’re just making yourself sound needy and like someone who could be controlling in the future.”
Ask: What’s the weirdest thing you’ve ever done?
“We’re all a little quirky, right? This is how you pry out those hilarious stories about living on a llama farm, appearing on an episode of Slime Time Live as a kid, or swapping lives with their identical twin for a day back in high school, or whatever,” says Orenstein. Everyone (okay, except maybe a narcissist)is nervous on a first date, and this question can help you both open up, laugh, and not feel like you have to be so formal. A date should be fun, after all.
Originally published June 20, 2018. Updated September 19, 2018.
Now, once you start seeing someone, whatever you do, don’t start orbiting. And here are tips for staying happy (and sane!) while navigating the online dating world.
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