21 Questions Game: Dig Deep with Fun and Flirty Questions (2024)

Want to get to know someone on a deeper level? The classic "21 Questions" game has all the right questions to help you get to know someone better, whether it's your best friend or your crush. We've rounded up the most interesting questions to spark great conversations about anything and everything. With fun questions like these, you'll literally never run out of things to talk about. (If you're looking for other fun things to keep you busy, we've got you covered with these game ideas.)

How to Play the 21 Questions Game

Playing 21 questions is super simple and straightforward. You can play with two or more people. I If you're playing with two people, you and the other person take turns answering questions. You can also modify this by having one person answer several questions in a row (or all 21 questions) before reversing roles and having the other person answer questions.

If you're playing in a group, the first player can choose a question and then the group can go around one by one and answer that question (with the person who asked the question going last). After everyone answers, the next player chooses a question and everyone answers again, and so on.

You can set rules that allow each player to skip a turn (or multiple turns) if they don't feel comfortable with the question— or you can play in hard mode and make it mandatory to answer every single question.

Now, onto the list of questions! Ahead, you'll find more than 21 questions (gotta account for those potential skips), including additional flirty questions that are perfect if you happen to be playing with a crush.

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?

21 Questions Game: Dig Deep with Fun and Flirty Questions (2024)

FAQs

What are some flirty 21 Questions? ›

If you're playing with your crush or on a first date, consider these flirty questions your go-to.
  • Do you believe in love at first sight?
  • What was your first kiss like?
  • What was your best kiss like?
  • What was your first impression of me?
  • What's your idea of a perfect date?
May 5, 2021

What are some juicy 21 Questions funny? ›

Best juicy questions
  • Where is your favourite place to be kissed?
  • And where is your favourite place to kiss someone?
  • Have you ever sent a nude photograph?
  • Have you ever received a nude photograph from someone else?
  • What attracts you to someone else?
  • What do you wear to bed?
  • Have you ever had a sexy dream about someone?
Dec 15, 2023

What are the flirty questions in 20 questions game? ›

Flirty Questions for Your Crush
  • Do you enjoy being single or do you want to find a serious relationship?
  • What's the craziest thing you've ever done on a first date?
  • Do you believe in love at first sight?
  • What's the weirdest thing you've ever put in your mouth?
  • What's your most R-rated guilty pleasure?

How to play 21 Questions with your crush? ›

The game typically starts with one person asking a question, and the other person answering it. The roles then switch, with the other person asking a question and the first person answering it. This continues until all 21 questions have been asked and answered.

What is a playful question flirty? ›

Flirty questions to ask a girl you just met. When is the last time someone made you blush? If we could spend the whole night together, what would you want to do? If your life was a rom-com, what would your theme song be?

What are 21 flirty questions to ask a guy to make him? ›

Flirty Questions to Ask a Guy
  • What's your love language?
  • Do you have a go-to pick-up line?
  • What's your flirt style?
  • What do you find the most attractive about other people?
  • What's your idea of the perfect date?
  • How do you know you really like someone?
  • Do you ever make the first move?
Jul 28, 2023

Is 21 Questions a flirty game? ›

21 questions game flirty

Spice up your conversations with the ultimate flirty 21 questions game. Discover creative and exciting questions to get to know someone better and add some playful charm to your interactions.

Is 20 Questions flirting? ›

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.

What are some spicy 21 Questions to ask your crush? ›

Dirty Questions to Ask Your Crush
  • What are your biggest turn-ons?
  • What's your favorite sex position?
  • How do you feel about one-night stands?
  • What are your biggest turnoffs?
  • Do you like sexting?
  • Where's the hottest place you've had sex?
  • How do you feel about PDA?
  • Have you ever had sex in public?
Apr 8, 2024

What are 21 juicy questions to ask a guy? ›

Flirty questions to ask a guy
  • What do you find most attractive about me?
  • What would our first date look like?
  • What are you like as a boyfriend?
  • What's your love language?
  • When are you going to ask me out?
  • When was the last time you felt butterflies?
  • What does love mean to you?
  • What's the worst pick-up line ever?
Dec 29, 2023

What are 21 juicy questions to ask your crush? ›

Questions to Ask Your Crush
  • Do you think double texting is a big deal?
  • What's the most embarrassing thing you've ever done to get a crush's attention?
  • Have you had your first kiss?
  • When did you have your first kiss?
  • Do you believe in astrology? ...
  • What's the most spontaneous thing you've ever done?
Feb 23, 2023

What are some flirtatious questions? ›

Flirty questions to ask a girl over text: 9 examples to try
  • What are you doing right now? ...
  • Should we send voice messages instead? ...
  • Which emojis do you use most often? ...
  • What are your biggest turn-ons? ...
  • What are your turn-offs? ...
  • Who was your first crush? ...
  • What's your favorite way to relax? ...
  • Have you ever been naked in public?
Oct 7, 2022

How to play 21 questions for adults? ›

The game “21 Questions” is a great game to play if you are trying to get to know someone, whether they're a friend or romantic partner. Playing the game is super easy—you just ask someone 21 questions and they have to answer each one honestly. Unlike other question games, these questions are typically more personal.

What are hot questions to ask your crush? ›

Hot Dirty Questions to Ask Your Crush
  • If I was in your room right now, what would you want to do to me?
  • What's your take on one night stands?
  • Have you ever had a one night stand?
  • Have you ever slept with someone, then woke up wishing you hadn't?
  • Would you ever sleep with your ex's best-friend?

What questions make a girl blush? ›

Flirty Questions to Ask A Girl You Like Over Text
  • Where did you learn to be so pretty?
  • What is the first thought that comes to your mind thinking about me?
  • Do you think I am romantic?
  • In one sentence, how would you sum up romance?
  • Do you think love is important in life?
  • Have you ever flirted with a guy?
Mar 14, 2024

What are some good flirty questions? ›

Flirty questions to ask your crush
  • If you were in a relationship right now, who would your celebrity pass be?
  • What makes for a perfect date, in your opinion?
  • What's the most romantic thing someone has ever done for you?
  • What's the hottest thing someone has ever done for you?
  • How would you define sex appeal?
Mar 28, 2024

Is 20 questions flirting? ›

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.

What are some juicy 21 questions to ask your crush? ›

Here are 21 questions you can ask your crush to get to know them better:
  • What's something that always makes you smile?
  • If you could travel anywhere in the world, where would you go and why?
  • What's your favorite thing to do on weekends?
  • Do you have any hidden talents?
  • What's the most adventurous thing you've ever done?
May 8, 2017

What are some spicy 21 questions to ask your crush? ›

Dirty Questions to Ask Your Crush
  • What are your biggest turn-ons?
  • What's your favorite sex position?
  • How do you feel about one-night stands?
  • What are your biggest turnoffs?
  • Do you like sexting?
  • Where's the hottest place you've had sex?
  • How do you feel about PDA?
  • Have you ever had sex in public?
Apr 8, 2024

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