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 do you 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 are some juicy 21 questions for crush? ›

Juicy Questions to Ask Your Crush
  • Have you ever been in love?
  • Have you ever broken someone's heart?
  • What's your most memorable kiss?
  • Is there anything you refuse to compromise on?
  • What's an automatic swipe right for you?
  • Are you a good kisser?
  • What was the worst date you ever went on?
Apr 8, 2024

How to tease your crush? ›

Tease them gently about something they're good at/confident about. If your crush is a star athlete, try saying, "So how many extra goals is your team going to score when they don't have you on the field?" Or, you could say, “With the high grades you get, I'm starting to wonder if you're bribing the teachers!”

Is 20 questions flirty? ›

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 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

How do you spice up 21 questions? ›

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?

What questions impress a girl? ›

Romantic Questions to Ask Your Girlfriend
  • What makes you feel loved?
  • What's your love language?
  • How do you express love to other people?
  • Do you believe in love at first sight?
  • Where should our next vacation be?
  • What do you imagine our future house looking like?
  • When did you realize you loved me?

What are 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

What is a good spicy question? ›

What's your biggest sexual fantasy?” “Morning sex or evening sex?” “Do you prefer giving or receiving?” “Do you prefer being on top or bottom?”

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