21 Questions Game: Dig Deep with Fun and Flirty Questions (2025)

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 (2025)

FAQs

What are some juicy 21 questions? ›

Best juicy questions for the 21 questions game
  • 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?
May 16, 2024

What are some flirty 21 questions? ›

Bonus: Flirty Questions to Ask Your Crush
  • 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?
  • Someone just asked you on your dream date. ...
  • What are three things you are looking for in a partner?
Jun 19, 2024

What are some spicy Q&A questions? ›

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

Is 20 questions a flirty game? ›

This time-honored flirting tradition of having loads of questions to ask your crush is one of our generation's best, and that goes for dating in your 20s, too.

What are spicy 21 questions? ›

Spicy 21 Questions Exclusively for Couples
  • What's one thing you've always wanted to try in the bedroom but haven't told me?
  • Where is the most adventurous place you'd like to make love?
  • What's a secret fantasy you've never shared with anyone?
  • How do you feel about role play, and what scenario intrigues you?
Mar 4, 2024

What is 21 freaky questions to ask a guy? ›

Freaky questions to ask a guy
  • Would you like it if I sent you dirty texts at work?
  • Have you ever had multiple sexual partners in the space of 24 hours?
  • Have you ever had a threesome?
  • What do you think about friends with benefits? ...
  • What's the sexiest thing I can do for you in the bedroom?
Nov 2, 2023

What is a playful question flirty? ›

“If you could ask me any question you would like, what would it be?” “What's the craziest thing you've ever done?” “What's the most spontaneous thing you've done?” “Would you ever go on a date with someone you've just met?”

What flirty questions can I ask my crush? ›

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

What deep questions to ask your crush? ›

Questions to Ask Your Crush to Get to Know Them Better

What are you most looking forward to? What is the most flattering praise you've ever received? What similarities can you see between us? What is something you've done that you believe everyone should try?

What deep questions to ask a guy? ›

Personal questions to ask a guy
  • What's the longest relationship you've ever had?
  • Do you believe in soul mates?
  • What's your biggest fear?
  • What's the most useless advice you've ever gotten?
  • What's your favorite memory?
  • What do you do every night before bed?
  • What does being a man mean to you?
Dec 29, 2023

What are 21 juicy questions for couples? ›

Flirty 21 Questions Ideas
  • Do you believe in love at first sight?
  • What is your dream date?
  • What do you consider the most romantic travel destination in the world?
  • What is your biggest fear when it comes to relationships?
  • Romantic lunch picnic in the park or a high-class dinner and cocktails?
  • What's your biggest turn-on?
Apr 24, 2024

What are 21 juicy questions to ask a girl flirty? ›

Best Flirty Questions to Ask A Girl
  • What's the wildest thing you've ever done for love? ...
  • What do you think is the sexiest thing about you? ...
  • Where is your favorite place to make love? ...
  • What do you think would happen if we were stuck in a room for 24 hours together? ...
  • Who's your celebrity crush?
Sep 21, 2023

What are good hot questions? ›

Higher Order Thinking Skills (HOTS)
  • What do you think could have happened next?
  • Do you know of another instance where...?
  • What would you change in the story?
  • From the information given, develop a set of instructions about ...?
  • What do you see as possible outcomes? ...
  • Why did ..... ...
  • What was the turning point?

What are the most juiciest questions? ›

Juicy questions to ask friends
  • What's the weirdest thing you've done in public?
  • What's an embarrassing thing you've done and never told anyone about?
  • What's the most bizarre text you've ever received?
  • What's the cringiest thing you've ever put up on social media?
Apr 18, 2024

What questions to ask a guy juicy? ›

Juicy Questions To Ask Your Partner
  • What's the craziest thing you've ever done?
  • What's something you've always wanted to try but haven't yet?
  • Have you ever had a one-night stand? ...
  • What's your favorite part of my body?
  • What's the most romantic thing you've ever done for someone?
  • What's your opinion on open relationships?
Apr 17, 2023

What are juicy questions for girls? ›

Dirty Questions to Ask Your Girlfriend
  • What makes you feel sexy?
  • Do you like PDA?
  • Do you feel satisfied in the bedroom?
  • What fantasies have you never told me about?
  • Is there anything non-sexual I do that turns you on?
  • Do you like when I wear lingerie?
  • Do you want to be gifted lingerie?
Apr 10, 2024

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