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)
Photo: Stock-Asso, Shutterstock

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

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

In either context, the latter question is too broad to start a meaningful conversation. Any time I’ve felt a connection on a first date, it’s because we organically discovered we both love the same episode of the same show, or think a certain musician is overrated, or want to become regulars at the same restaurant. I’ve never felt a spark after someone asked if I’m “passionate” or “care about honesty.” So many well-meaning first-date questions end up being too vague or 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 significantly more leeway to get a conversation flowing once you’ve got a real, live person in front of you. But just like the apps, all the best questions you can ask should be specific, original, and personalised. And considering the classic first-date pressure to fill every moment of silence, you won’t be sorry to have some prepared questions ready to go. So here are some terrible questions you should avoid asking on a first date, and what you should ask instead.

Avoid these first-date questions

I’m going to give you the benefit of the doubt and assume that you aren’t even considering questions like, “what do you weigh?” or “do you think you could outrun me?” or “can you watch my cat this weekend?” I will instead assume that you mean well, but struggle to get generate conversational sparks sparks when meeting someone new. The following questions are well-intentioned, but so boring or so off putting that your date will likely start plotting their escape.

  • “So, what’s your story?” This is the “tell me about yourself” of romantic pursuits. Not only is it impersonal, it’s so open-ended that you don’t give your date a meaningful avenue to answer it. A good first date will give you something to work with as a follow-up, but you better deliver with specificity and originality after blowing it on this first question.
  • “Why are you still single?” Some people try to spin this into a pick-up line or compliment or sorts. (“You’re so great…how are you still single?”) Even if you’re trying to be flirty, think logically about how this will play out. The other person might respond with a coy “Oh, who can say…” but internally, they’re thinking about how backhanded your “compliment” feels. Now they’re scrambling to steer the conversation away from why they’re actually single, like their deep-seated commitment issues. Or worse, you’ve now opened the doors for them to steer the conversation into their deep-seated commitment issues.
  • “What attracted you to me?” Again, a misguided attempt at flirtation. This question in particular will sound either too arrogant or too insecure. Either way, don’t go fishing for compliments.
  • “What are your hobbies?” Too generic. Ideally, they’ll have casually hinted at one of their hobbies in conversation or you’ll have a little knowledge going into the conversation. From there, ask specific questions about how, when, and why they do whatever it is they do.
  • What’s your family like?” I believe that talking about family is fair (and often fascinating) territory on a first date. However, you have to personalise this one. If you’re feeling confident, you could try and guess whether or not they’re the middle child, or you could ask them if they’re close with their parents. Avoid “did you cause your parent’s divorce?” or “why aren’t you on speaking terms with your father?” Keep it light.
  • “Red or white wine?” Red. You? White? Cool. Great talk.

Try these first-date questions instead

Here are some thought-starters if you want to actually get to know your date. The key is to make the other person feel comfortable and interesting. While propping them up, you’ll simultaneously set yourself apart as someone who is original, confident, and considerate.

  • “Which holiday is the absolute best one, hands-down?” Strong stances are important, so long as you’re keeping it low stakes and playful. With the best holiday question, you can open the door to hearing about their family, traditions, favourite time of year, food preferences — not to mention their overall creativity with the answer. Questions like this one are perfect for flirty banter.
  • “What were you like as a kid?” This gives the other person an opportunity to talk about themselves and their personality, but with a little more distance than if you directly asked them to describe themselves right now.
  • “Would you rather…” A “would you rather” prompt is perfect for showcasing some personality, without the pressure of the divulging too much personal information, too soon. These kinds of questions could be innocent, flirty, deep, or whatever your vibe happens to be. For instance: “would you rather sleep with your closest friend or your worst enemy?” or “would you rather be able to read minds (but you can never turn it off) or be able to turn invisible for one day every year?”
  • “What did you do today?” Yes, I know this seems basic. I know it seems like I’m contradicting my own advice to always be specific. It’s crucial that you’re still, well, normal. If your first question upon meeting your date is a “would you rather…” you risk coming across as forcibly quirky. You still need this type of question in order to get to know what they other person is like, what they like to talk about, and make sure you’re both comfortable getting into the swing of things. Plus, “what did you do today?” is still more specific and fruitful than an open-ended “how was your day?” The takeaway here: Don’t come on too strong (“ranch or blue cheese?”) without covering common pleasantries first.
  • “If you had 24 hours to do whatever you wanted, what would you do?” This one is silly and imaginative, providing a lot of opportunity for back-and-forth, and it will reveal a lot about people’s priorities and imagination and all that crap.
  • “Who did you vote for?” Controversial, but a time-saver.

The takeaway: Be interesting, but be yourself

Unfortunately, the most important part of a first date is figuring out how to be yourself. My advice to choose questions that are specific and original is worthwhile, but it can’t take the place of allowing conversation to flow as naturally as possible. Well-considered questions are a good start, but a date also shouldn’t feel like a job interview or an interrogation.

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