57 First Date Questions That Get Real, But Keep It Fun

Updated March 2, 2021
Meeting for date

First date questions can help you learn a little bit more about that potential special someone and suss out whether you want to go on a second date with them. Since first impressions really do mean everything, you want to make sure that you ask the right questions kind of questions to instantly connect with your date.

Funny First Date Questions to Ease the Tension

Funny questions can help lighten the mood on a first date and give you some great memories to look back on if your new relationship lasts. Think of questions that'll keep the mood light but will still provide answers that give you important information about your date and help him or her feel comfortable.

  • If you felt the need to escape this date, how would you do it without being rude?
  • What's one thing in your pocket/purse right now that would make me laugh?
  • What song lyric is stuck in your head right now?
  • Which movie are you most embarrassed to admit you enjoyed?
  • Which awkward conversation starter should we try first, the weather or the food here?
  • What's your go-to party story?
  • What's the worst first date you've ever had?
  • What's the funniest thing you've ever done while inebriated?
  • What's the most socially unacceptable thing you've ever done?
  • What's your favorite household item?
  • If you had to give up one appliance for a year, what would it be?
  • What never fails to make you laugh?
  • What's the most outrageous thing you've ever bought?

Creative Getting to Know You Questions for a First Date

Stand out from all the other viable relationship candidates by asking creative questions that speak to your personality and help you get to know your date. Look for ways to skew standard first date questions toward your own interests, hobbies, and life goals.

  • If you had to choose one genre of music to play in the background of your whole life, which would you choose?
  • What's the longest you've ever spent binge-watching Netflix?
  • Would you rather have to take a bath every day or only be allowed to shower every three days?
  • Which endangered animal would you save if you could only choose one?
  • What's the first book title that comes to your mind right now?
  • What's the most interesting documentary you've ever seen?
  • If we got on a plane right now, where we would be flying to?
  • What do you think the best era for music was?
  • What food do you love that most people hate?
  • What's your opinion on astrology?
  • What's your dirtiest secret?
  • Would you consider yourself a morning or an evening person?
  • How many close friends would you say you have?
  • What's the best piece of advice you were ever given?
Couple talking at table with cocktail and beer

Interesting Questions to Get to Know Your Date

Most people know what to expect from first date conversations, so you'll want to keep your date on their toes by asking some interesting questions, like any one of these.

  • Which place have you visited that you never want to go back?
  • What was your favorite family vacation you took as a kid?
  • What's the worst thing you've gotten away with at work?
  • What quirk do you have that would annoy people the most?
  • What feature of yours do you wish people would compliment more often?
  • What hobby do you have that you wish you were better at?
  • When's the last time you broke up with someone?
  • What does your dream home look like?
  • Do you consider yourself more of right-brain or left-brain kind of person?
  • What's one mundane memory that's stuck with you for years with seemingly no reason why?
  • What do you think your love-language is?
  • What's the first thing that you normally notice about a person?
  • What's your typical workday look like?
  • What's your favorite weird food combination?
Awkward first date

Deep Questions to Ask on a First Date

Start with probing questions that require introspection from your date without making them feel uncomfortable. These questions should be about your date's personality, goals, and views, not their deepest, darkest secrets, so you can begin to see just how compatible the two of you might be.

  • What three words would your mom use to describe you?
  • Would your boss choose you as his/her replacement?
  • If you could only choose one charity to donate to or volunteer for the rest of life, which would you pick?
  • What's your most embarrassing childhood memory?
  • Which of the seven deadly sins do you commit the most often?
  • What's your biggest irrational fear?
  • What would your best friend say your worst quality is?
  • How important is religion to your life?
  • What quality do you like best in a partner?
  • When I say "love," what's the first thing that comes to your mind?
  • Why do you think you're still single?
  • When you get into an argument, what's your typical reaction look like?
  • Do you believe that everyone has that 'one' person they're meant to be with?
  • Which is more important to you - emotional intimacy or physical intimacy?
  • Where do you see your next relationship ending up (marriage, casual-fling, and so on)?
  • If you could tell your younger self one piece of advice, what would it be?

Communicating With Your Date

Have fun with these questions and learn about the person who, if things go well, may just end up as your soul mate. You want to try your best not to make a fool of yourself, but if you stumble over your words or say the wrong thing, don't worry; chances are the other person is just as nervous about making a great first impression. With any of these first date questions you'll never have to fear about finding something to say to break an awkward moment of silence, and you should be able to leave the date feeling, at the very least, closer to the person you just chatted with for hours.

57 First Date Questions That Get Real, But Keep It Fun