Questions You Should Never Ask on a First Date (And What to Ask Instead)

Questions You Should Never Ask on a First Date (And What to Ask Instead)

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I wouldn’t go so far as to call a first date a “job interview.” At the same time, a few valuable job interview tips and tricks can also increase your chances of a successful first date. You want to put your best foot forward, make the conversation feel natural, and gather crucial information about the person sitting across from you.

The 5 WORST First Date Questions (and What to Ask Instead)

Think about your last job interview. It was probably much easier for you to answer a specific question like, “Tell me about a time you overcame a challenging situation at work?” than the vague, open-ended, oh-so-dreaded “Tell me about yourself.”

In both contexts, the last question is too broad to start a meaningful conversation. Every time I’ve felt a connection on a first date, it’s been because we’ve spontaneously realized we both love the same episode of the same TV show, or think a certain musician is overrated, or want to be regulars at the same restaurant. I’ve never felt a spark after someone asks me if I’m “passionate” or “value honesty.” So many well-meaning first date questions end up being either too vague, or too boring, or both.

So, what’s a single person to do? Luckily, compared to your one shot at getting a quality response on the apps, you have considerably more wiggle room to spark conversation when you have a real, live person in front of you. But just like on the apps, all the best questions to ask need to be specific, original, and personal. And given the classic pressure of a first date to fill every moment of silence, you won’t regret having a few prepared questions at the ready. So here are some terrible questions not to ask on a first date, and what to ask instead.

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