Sex, Dating & Relationship

21 Questions Game: Dig Deep with Fun & Flirty Questions

Would you like to know someone better? Whether it’s your best friend or your crush, the timeless “21 Questions” game features all the greatest questions to get to know someone better.

21 Questions Game: Dig Deep with Fun & Flirty Questions

We’ve compiled the best inquiries to start fascinating discussions on everything and everything. You won’t ever run out of topics to discuss if you ask engaging questions like these. (If you’re seeking for more enjoyable activities to occupy your time, check out these gaming suggestions.)


How to Play the Game of 21 Questions

The game of 21 questions is quite easy to understand. There is room for two or more players. I When playing with a partner, you both alternate who responds to the questions.

This can also be changed by having one person respond to a string of questions (or all 21 questions) before switching roles and having the other person respond.

If you’re playing in a group, the first person can pick a question, and everyone else in the group can answer it one at a time (with the person who asked the question going last). The next person picks a question, and after everyone responds, everyone answers once again.


You can either play in hard mode and require answers to every question, or you can specify rules that allow each player to skip a round (or many turns) if they don’t feel comfortable with the question.

On to the list of inquiries! There are additional flirting questions that are ideal if you chance to be playing with a partner beyond the first 21 questions (must account for those potential skips).

21 Questions Game: Dig Deep with Fun & Flirty Questions

21 Questions List

  1. What’s the weirdest dream you’ve ever had?
  2. If you could travel to any year in a time machine, what year would you choose and why?
  3. If you could change one thing about yourself, what would it be?
  4. What’s one of the most fun childhood memories you have?
  5. If you could have dinner with a famous person (living or dead), who would you choose?
  6. What’s your favorite movie to watch over and over again?
  7. What’s your favorite season of the year?
  8. Who is your celebrity crush?
  9. What’s your biggest fear?
  10. What’s the wildest thing you’ve ever done?
  11. What’s the best advice you’ve ever received?
  12. What’s a bad habit you had that you’ve been able to overcome?
  13. What’s your dream road trip destination?
  14. What’s your favorite food of all time?
  15. What are three items on your bucket list?
  16. What’s your biggest regret?
  17. What’s your favorite thing about yourself?
  18. What’s the weirdest thing in your closet?
  19. If you had to guess what people appreciate you the most, what would you say?
  20. What’s your dream job?
  21. If you could be a part of a family on any TV show, which family would you choose?
  22. Of all the personal questions I could ask you, what’s one you wouldn’t want to answer?
  23. What’s your biggest pet peeve when it comes to social media?
  24. Who’s your favorite character from literature?
  25. What’s an activity that you do not find fun at all?
  26. What’s your favorite color to wear?
  27. What’s your favorite type of dessert?
  28. What’s the worst lie you ever told as a kid?
  29. Who in your family are you closest to?
  30. What’s your favorite sport to play and why?
  31. If we were in the middle of a zombie apocalypse, who are three people you’d want on your team?
  32. If you were an ice cream flavor, what would it be?
  33. What’s your favorite song to sing in the shower?
  34. What’s one thing your mom or dad doesn’t understand about you?
  35. If you had a kid, what would you name it?

Bonus: Flirty Questions to Ask Your Crush

These intimate questions work especially well for a love interest, since they’re all romance-related. If you’re playing with your crush or on a first date, consider these flirty questions your go-to.

ALSO READ: 15 Ways To Make Your Woman Scream Your Name During Séx

21 Questions Game: Dig Deep with Fun & Flirty Questions
  1. Do you believe in love at first sight?
  2. What was your first kiss like?
  3. What was your best kiss like?
  4. What was your first impression of me?
  5. What’s your idea of a perfect date?
  6. What are three things you are looking for in a partner?
  7. What makes you automatically swipe left on a person?
  8. Have you ever experienced true love?
  9. If you had a conversation with your ex, what’s a question you’d want to ask them?
  10. What are the most frequently used emojis in text conversations?
  11. What’s the wildest thing you’ve ever done to get someone’s attention?
  12. What’s your biggest fear when it comes to relationships?
  13. What’s the most embarrassing thing you’ve ever done in front of someone you like?
  14. Do you find first dates fun or stressful?
  15. What’s your favorite movie couple and why?
  16. What’s your favorite place to take a significant other?
  17. Who’s relationship do you admire and why?
  18. At what point in a relationship do you think it’s time to go public on social media?
  19. What’s your biggest turn on?
  20. What’s your biggest turn off?
  21. What’s your favorite thing about me?
  22. What was the last flirty text you sent?
  23. What’s the worst thing about being single?
  24. What’s the best thing about being single?
  25. Would you consider yourself a hopeless romantic?
  26. At this point in your life, would you prefer a casual relationship or a serious relationship?
  27. What’s the hardest part about being in a long-term relationship?
  28. If you were getting married, would you write your own vows?
  29. What’s your biggest regret when it comes to a past relationship, specifically?
  30. How do you get over a breakup?
  31. What meme best represents your life?
  32. Would you rather love and lose, or never love at all?
  33. After a disagreement, do you initiate the makeup conversation or wait for your S.O.?
  34. How many people have you told “I love you” to in a romantic context?
  35. What’s the silliest excuse you ever used to get out of a date?

Looking for more fun games and conversation starters? Then check out Best Truth or Dare Questions, 103 This or That Questions, and 71 Good Questions to Ask Your Best Friends.

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