60 Important First Date Questions

Michele Meleen
Meeting for date

First date questions can help you find out whether you want to go on a second date with someone. Since first impressions are everything, you want to make sure you ask the right questions in the right way.

Funny First Date Questions to Ease Tension

Funny questions can help lighten the mood on a first date and give you some great memories to look back on if your relationship lasts. Think of questions that sound funny to say, but provide answers that give you important information about your date and help him or her feel comfortable with you.

  • 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?
  • Who's funnier, Chris Rock or Kevin Hart?
  • What's the weirdest thing you imagined might happen on this date?
  • What song lyric is stuck in your head right now?
  • Which movie are you most embarrassed to admit you enjoyed?
  • Which is better, funny cat videos or funny baby videos?
  • Which awkward conversation starter should we try first, the weather or the food here?
  • What's the funniest thing you ever learned about someone on a first date?
  • What one irrational fear scares you the most?

Flirty First Date Questions That Show You're Interested

By asking flirtatious questions you're letting your date know in a subtle way that you're into them. Flirting doesn't automatically imply that something sexual will follow on a first date. Keep your questions PG-13 at most and they'll come across as flirty, not forward.

  • You smell great, what is your favorite scent?
  • Do you dress like this all the time or just for special occasions?
  • Do you always smile this much?
  • Are you wearing contacts, or is that your natural eye color?
  • How long after this date before I hear from you again?
  • If this date keeps going great, how would you suggest we extend it?
  • If you were stranded on a desert island with only one picture of a woman's/man's body part, which body part would you want it to be?
  • What is your typical response when people tell you you're handsome/beautiful?
  • If we could jump on a plane and fly anywhere together right now, where would you want to go?
  • How do you politely decline all the men/women who must hit on you?
Couple talking at table with cocktail and beer

Deep Questions to Ask on a First Date

Start with probing questions that require introspection from your date without making them uncomfortable. These questions should be about your date's personality, goals, and views, not their deepest, darkest secrets.

  • What's your relationship superpower?
  • What three words would your mom use to describe you?
  • What is your ultimate goal in life?
  • Would your boss choose you as his/her replacement?
  • What parenting style do you think works best?
  • What do you think is the biggest issue faced by children today?
  • What decade sums up your relationship style best?
  • If you had to choose one genre of music to play in the background of your whole life, which would you choose?
  • Which famous actress would you pick to play your soul mate in the movie of your life?
  • If you could only choose one charity to donate to or volunteer for the rest of life, which would you pick?

Awkward Questions That Are Important on a First Date

First dates should be light and fun, but they're also important measures of whether the other person is deserving of your time. While it's great to keep things light, there are some important questions you'll want to get from the start that might feel embarrassing to ask.

  • Do kids have a place in your future?
  • What is your top relationship deal breaker?
  • How many people is too many people to date at one time?
  • Is monogamy natural or a construct created by humans with an agenda?
  • Do you believe in evolution?
  • Would you be upset if you lost the right to vote?
  • Which is more important to you, gun control or population control?
  • How often do you talk to your parents?
  • On a scale of one to ten, how comfortable are you with your finances?
  • Which Star Wars movie title best describes your living situation? (Solo: lives alone, Return of the Jedi: lives with parents, Attack of the Clones: lives with roommates, etc.)
Awkward first date

Uncommon and Unexpected First Date Questions

Most people know what to expect from first date conversations. Keep your date on his or her toes and ask some unexpected questions that can lead to more important discussions.

  • Which reality dating show best describes your current love life? (The Bachelor, Are You the One?, Ex on the Beach, etc.)
  • What's the most dates you've ever been on in one day?
  • Have you ever taken someone on a first date out for breakfast?
  • What's one dating trend you'd like to see changed most?
  • If you could invent a dating app, what would make it different from all the others?
  • What is the most underrated first date location?
  • How much did you spend on your most expensive date?
  • If you were on Shark Tank, what would your proposed company or product be?
  • What's the last historical landmark or location you visited?
  • Have you ever thought about moving to another country?

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.

  • 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?
  • If you had to choose one fad diet to try, which would it be?
  • If you could do yoga with any farm animal, which would you choose?
  • If you were a celebrity, would you let Madame Tussauds make a wax figure of you?
  • Which Keeping Up With the Kardashians character best imitates you?
  • If you could be on any TV talk show, which one would you pick?
  • What's the first book title that comes to your mind right now?
  • If the zombie apocalypse started right now, how would you protect me from the zombies?

Don't Ask Relationship Questions on a First Date

When asking first date questions, be sure to ask him or her while in a discussion so you're not firing off question after question. If you sense your date doesn't like the question you asked, do not push the issue. If you don't feel comfortable answering a question yourself, don't expect your date to answer it. While these general topics might be important for relationships, these questions should be avoided at all costs on your first date.

  • Which current presidential candidate is your frontrunner?
  • How soon is too soon to get married after a first date?
  • What are the odds of something physical happening on this date?
  • When were you last tested for STIs?
  • Which financial bracket best describes your number of sexual partners? (lower class, middle class, high class, etc.)
  • Are you living within your means?
  • Which part of my physical appearance would you most like to change?
  • Which serial killer would you most like to have lunch with?
  • Which religion would you eliminate from the world if you had to choose?
  • Have you ever thought about physically harming another person?

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 stutter or say the wrong thing, don't worry; chances are the person is too self-conscious about him or herself to notice. Remember, it's best to ask first date questions when there is an awkward moment of silence or during a discussion of a similar topic.

60 Important First Date Questions