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)
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