How to Play 21 Questions: A Fun and Simple Way to See If Your Crush Is Right For You (2023)

Having a crush can be such an exhilarating time. But before you make things official, there are a few things you have to do — like, you know, actually get to know them. When you first start talking to your crush, you want to discover things that help you learn more about them. The best questions to ask your crush ignite genuine, meaningful conversations that reveal a glimpse into who they truly are.

If you tend to get nervous around your crush and go silent, or feel like your convos don’t really go anywhere — maybe because you’re both shy or new to this whole dating thing — it may be time to try the 21 Questions game. This fun dating game not only helps you get to know your crush better, but also creates a lively, engaging conversation that reveals those details that are usually a little harder to come by, like hopes, dreams, and values.

Whether you decide to play over text or IRL, the 21 questions you ask will help you really figure out who your crush is and how they see the world. So, if there’s someone new in your life and you’re looking for an interesting way to get to know them better, read ahead to find out how to play 21 Questions and discover all of the best questions to ask a crush.

How Do You Play 21 Questions?

Just ask your crush one question at a time! The game can be one-sided, but it’s typically more fun if you both play. Ask each other questions back and forth, or take turns answering all 21 questions in a row.

In a group setting, the same rules apply. Randomly choose one person to ask the first of the 21 questions, then move through the group until everyone has had a chance to answer.

This is optional, but a player can “pass” on questions if they don’t feel comfortable answering. Whether it be a single question or multiple, you can decide on exactly how many people are allowed to skip (if you want to set a limit).

You can choose any 21 questions you want, but to help, pick from the comprehensive list of questions we’ve put together below. Of course, 21 questions might not be enough to get to know someone — so we’ve included 100. That way, you will *never* run out of things to ask.

Questions to Ask Your Crush

1. Do you think double texting is a big deal?

2. What’s the most embarrassing thing you’ve ever done to get a crush’s attention?

3. Have you had your first kiss?

4. When did you have your first kiss?

5. Do you believe in astrology? Does your sign fit you?

6. What’s the most spontaneous thing you’ve ever done?

7. If you go to a restaurant and have terrible service, is it ever OK not to tip?

8. Have you ever cheated on your S.O.?

9. Have you ever been cheated on?

10. What’s your biggest regret?

11. What’s your dream date night?

12. How many S.O.s have you had?

13. Are you looking for a relationship?

14. What do you consider a red flag in a relationship?

15. What is your love language?

16. How do you usually react to conflict in a relationship?

17. Who do you consider your best friend?

18. What do you value most in your friendships?

19. Have you ever gone through a friendship breakup?

20. What do you consider dealbreakers in a relationship?

How to Play 21 Questions: A Fun and Simple Way to See If Your Crush Is Right For You (1)


Questions to Get to Know Someone Better

1. If your life was a movie, what would it be called?

2. What was the last concert you went to?

3. What do you wish you were really good at?

4. If you were a dog, what kind of dog would you be?

5. Do you believe in aliens?

6. Do you shower at night or in the morning?

7. What’s the most cringeworthy outfit you’ve ever worn?

8. If you could be any animal, what would you be?

9. Would you rather leave your hometown and never be able to return, or stay in your hometown but never be able to leave?

10. If you had to rename yourself, what name would you choose?

11. What was the last show you binge-watched?

12. If you had a time machine, would you go back in time or visit the future?

13. If you could only hear one song for the rest of your life, what would it be?

14. What is the worst lie you’ve ever told your parents?

15. If any actor or actress could play you in a movie, who would it be?

16. What’s your favorite song lyric?

17. When was the last time you felt most yourself?

18. What do you think my superpower is?

19. What is your dream job?

20. What does your ideal weekend look like?

21. What is something that people misunderstand about you?

22. What is something that you would change about your life?

23. What do you think is your best quality?

24. What are you most scared of?

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25. Do you have any insecurities?

26. How would you describe yourself in three words?

27. When is your birthday?

28. Do you have any siblings?

29. Who’s your favorite author?

30. Is there one book that changed your life or had a lasting impact?

31. What is your all-time favorite TV show?

32. What is your favorite childhood memory?

33. Who do you feel your closest to in your family?

34. When do you feel most confident?

35. Where do you see yourself in 5 years? 10 years?

Juicier Questions

1. How many people have you kissed?

2. Do you ever think about me?

3. What have you done sexually with someone else?

4. What attracts you to people?

5. What are your thoughts on sex?

6. Are you a virgin?

7. Do you think you’re a good kisser?

8. What turns you on?

9. Have you ever had a sexy dream?

10. What do you wear when you sleep?

11. What is the worst assumption someone has made about you?

12. Have you ever been in love?

13. Have you ever snuck out of the house? For what?

14. How did your last relationship end?

15. What was your first impression of me?

16. Do you believe in marriage?

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17. Do you believe in monogamy?

18. Do you want to have kids someday?

19. Who was your first crush?

20. Have you ever had your heart broken?

21. Do you think you’ve ever broken someone’s heart?

22. What have you learned from the other relationships in your life?

23. What was your longest relationship?

24. What was your shortest relationship?

Bonus Questions

1. What is the weirdest dream you’ve ever had?

2. What is on your bucket list?

3. Are you more of a morning or night person?

4. What is your go-to karaoke song?

5. If you could move anywhere in the world, where would you go?

6. What was one time you really stepped out of your comfort zone?

7. What is the biggest lesson you’ve learned ever?

8. What is your favorite movie of all time?

9. What is your biggest guilty pleasure?

10. If you were a superhero, what kind of secret identity would you have?

11. What would your younger self not believe about your life today?

12. If you won the lottery, what would you do with the money?

13. What three items would you bring with you to a deserted island?

14. Who is the last person you texted?

15. What is the last thing you searched for on your phone?

16. Who is your celebrity crush?

17. What is the one thing you can’t live without?

18. What is your all-time favorite meal?

19. Do you prefer to cook or order take-out?

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20. What’s your go-to take-out meal?

21. If you could live anywhere in the world, where would it be?

How to Play 21 Questions: A Fun and Simple Way to See If Your Crush Is Right For You (2)

    How to Play 21 Questions: A Fun and Simple Way to See If Your Crush Is Right For You (3)

    Tamara Fuentes

    Entertainment Editor

    Tamara Fuentes is the current Entertainment Editor at Cosmopolitan, where she covers TV, movies, books, celebrities, and more. She can often be found in front of a screen fangirling about something new. Before joining Cosmopolitan, she was the entertainment editor over at Seventeen. She is also a member of the Television Critics Association and the Latino Entertainment Journalists Association. Follow her on Twitter and Instagram.

    How to Play 21 Questions: A Fun and Simple Way to See If Your Crush Is Right For You (4)

    Jasmine Washington

    Assistant Editor

    Jasmine Washington is an Assistant Editor at Seventeen, where she covers celebrity news, beauty, lifestyle, and more. For the past decade, she has worked for media outlets, including BET, MadameNoire, VH1, and many others, where she used her voice to tell stories across various verticals. Follow her on Instagram.

    How to Play 21 Questions: A Fun and Simple Way to See If Your Crush Is Right For You (5)

    Leah Campano

    Associate Editor

    Leah Campano is an Associate Editor at Seventeen, where she covers pop culture, entertainment news, health, and politics. On the weekends, you can probably find her watching marathons of vintage Real Housewives episodes or searching for New York City’s best almond croissants.


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