Level Up Your Flirting Game With These “20 Questions” Topics

Get the conversation flowing over text or IRL.

Originally Published: 
these "20 questions" to ask your crush will get the conversation flowing
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When trying to get to know someone intimately, a classic game of “20 Questions” is the perfect way to do it. The flirty questions game from your childhood can be used in today’s dating world to get all the juiciest details you’ve ever wanted to know about your crush, and form a tight bond. (There’s even scientific evidence that shows asking personal questions can help two people feel more closely connected.) These twenty questions will help reveal the object of your desire’s wants, dreams, turn ons, and quirky habits.

The game is pretty simple. Just create a list of twenty questions, and ask your crush one question at a time. The game can be one-sided, or you and your crush can take turns asking each other the same questions from the list (either popcorn style or each person asking the other the twenty questions straight through). You can set your own rules for allowing players to skip turns (or multiple) if someone doesn’t feel comfortable answering a question — like a forfeit or a simple “pass.”

Now, on to the questions! Below, Bustle has outlined 60 (YWIA —“You’re welcome in advance!”) funny, deep, and flirty “20 Questions” to ask your crush, so you’ll never run out of things to talk about next time you’re hanging out.

Twenty Funny Questions

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  1. If a movie was made based on your life, which actor would play you?
  2. What are your three most frequently used emojis?
  3. If you could be any mythical creature, what mythical creature would you be?
  4. Who in your friend group would last the shortest in a zombie apocalypse?
  5. What’s the silliest lie you’ve ever told?
  6. What’s the funniest excuse you’ve ever made to get out of a bad date?
  7. What’s the craziest thing you’ve ever done?
  8. If a genie offered you three wishes, what would you wish for? (Funny answers only!)
  9. What would be the title of your comedy special?
  10. What do you do when you’re home alone?
  11. What’s an irrational fear that you have?
  12. On a scale of 1 to 10, how weird are you?
  13. What would your best friend say is your worst quality?
  14. Which historical figure do you think would be really funny on Twitter?
  15. If you were trapped in a fictional place for a year, where would you like to stay: Hogwarts or Narnia?
  16. What popular personality from the past do you think would be Instagram famous today?
  17. What’s the worst birthday you’ve ever had?
  18. What’s a weird, totally useless talent you have?
  19. What’s the weirdest fan fiction you’ve ever read?
  20. If you were a member of the Encanto family, what would be your gift? (Silly answers only!)

Twenty Deep Questions

  1. If you could live in another era, what era would it be?
  2. Which is more important to you: platonic friendships or romantic relationships?
  3. Would you rather your loved ones always be truthful with you or tell you lies to protect your feelings?
  4. Which do you value more: honesty or loyalty?
  5. If you could find out how you would die, would you want to know?
  6. You and another person of your choosing are the last people on Earth. Who are you living out your last days with?
  7. If you could have dinner with anyone living or dead, who would you dine with?
  8. What’s your philosophy on life?
  9. Would you consider yourself religious or spiritual?
  10. Have you ever lost someone close to you?
  11. Do you judge a book by its cover?
  12. Have you ever kept a diary?
  13. Have you ever broken someone’s heart?
  14. What are you most grateful for?
  15. Do you believe in second chances? Why or why not?
  16. What’s your biggest regret in life?
  17. What’s the greatest lesson you’ve learned so far in your life?
  18. What’s the greatest challenge you’ve ever had to overcome?
  19. If you could change anything about our current state of the world, what would it be?
  20. Why are we here?

Twenty Flirty Questions

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  1. What do you think your sun, moon, and rising signs say about you?
  2. What do you consider to be the sexiest song ever made?
  3. What’s a relationship dealbreaker for you?
  4. What do you like most about me?
  5. If we were to Netflix and chill, what movie would we watch (or not watch)?
  6. What’s the most over-the-top thing you’ve ever done for love?
  7. Are you friends with your exes?
  8. What’s your idea of a perfect date?
  9. Where would we go on our first date: movies or restaurant?
  10. If you came across my profile on Tinder, would you swipe right or left?
  11. What makes you automatically swipe left on a dating profile?
  12. What meme best represents your love life?
  13. In your opinion, why are you still single?
  14. Which celebrity would you hook up with if you had the chance?
  15. What are your thoughts on sexting?
  16. What turns you on?
  17. What’s a sex scene from a show or movie you’d love to recreate?
  18. Have you ever been in love?
  19. What was your first kiss like?
  20. What’s the most embarrassing thing you’ve ever done in front of a crush?

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