In the middle of a game night with friends, and looking for a simple and easy way to break the ice? Then a classic 21 Questions Game might be just what you are after—and we are here to help make it super easy for you.
Whether you want icebreaker questions for blossoming relationships or thought-provoking prompts to get to know someone better and deepen your bond, this handy list could be all you need to have a great time. No miscellaneous game boards, cards, or fancy extras. Just the device you are reading this on and at least one other person.
A 21 Questions Game is simple and the easiest way to really get to know what’s going on inside your best friend’s mind, not to mention the ideal setup for a perfect date. It’s fun, free, and can also be as flirty or as revelatory as you want it to be. All you need is an open mind.
This post includes a mix of questions meant to serve as conversation starters, as well as thorny topics that you might not otherwise dare to ask. There are also silly, flirtatious cues if that's more your vibe. The key thing is, you’ll always have a question to ask. Ready to play? Here’s what you need to know.
How to Play the 21 Questions Game
Playing 21 Questions is super easy, and it doesn’t require a specific number of people. It can be just you and one other person or a large group.
- If you're playing with two people, you and the other person should take turns answering questions. You can also switch things up by having one person answer several questions in a row (or all 21 questions) before reversing roles and having the other person answer questions. That said, if you’re playing 21 Questions during a date, especially a first date, it’s probably going to feel better and more natural to take turns answering. (The last thing you want is for a game to turn into an interrogation!)
- If you're playing with a group, the first player can choose a question from the list of 21, and then the group goes around one by one to answer it. Make sure the person who asked the question also has a go at answering, since the key here is learning more about everyone involved. After everyone answers, the next player chooses a question, and everyone answers again, and so on. If your group is too large, you can go in turns, asking a single question to a specific person. For example, the first person picks a question, and the person to their right answers it. Then that person picks another question and asks it to the person to their right, 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. It’s ultimately up to you, but keep in mind that if anyone wants to skip answering a specific question, it’s not cool to force them to answer. Consider giving that person an out and keeping the game rolling. If a question comes around that you feel embarrassed to answer, you’ll be glad you set the precedent of letting others off the hook!
Now, let's get cracking with the actual questions. Ahead, you'll find a lot more than 21 questions to ask (we have to account for those potential skips or multi-day plays!) during a 21 Questions Game. We’ve also included an additional list of mostly flirty questions that are perfect if you happen to be playing with a crush.
21 Questions List
From deep questions that’ll spark some real discourse to unique and random questions we’re pretty sure you haven’t heard before, choose any 21 (or more) of the following queries for your 21 Questions game.
1. What's the strangest dream you've ever had?
2. If you could travel back in time, what era would you choose and why?
3. If you could change one thing about yourself, what would it be and why?
4. What’s the very first thing that comes to mind when you think about fun childhood memories?
5. If you could have any fictional character's wardrobe, whose would it be and why?
6. What was the first job you ever wanted to have as a kid?
7. If you could have dinner with a famous person (dead or alive), who would you choose and why?
8. What is your favorite movie to watch over and over again?
9. If you were the lead character of a video game, which one would it be and why? (You can also make up your own video game concept.)
10. What is your favorite season and why?
11. What is your least favorite season and why?
12. If you could create your own holiday, what would it be called and how would it be celebrated?
13. What’s the most random thing you’ve ever bought online and why did you buy it?
14. If you could invent any gadget, what would it be and do?
15. What’s the worst thing you’ve done to get out of trouble?
16. What's your favorite museum and why?
17. What's your biggest fear and why?
18. What's the most adventurous thing you've ever done in your life?
19. What's the best and worst advice you've ever received?
20. You just won $100,000 to open your own business. What kind of business is it?
21. What's a bad habit you had that you've been able to overcome? And how did you do it?
22. Where would your dream road trip take place? Who would you take along with you?
23. What was your favorite food when you were a kid and why?
24. What are three items on your bucket list?
25. What's your biggest regret in life?
26. If you could only communicate via movie quotes, what movie would you choose and why?
27. What’s your favorite urban legend and why?
28. What's your favorite thing about yourself?
29. What's the weirdest thing in your wardrobe?
30. If you had to guess what people appreciate you for the most, what would you say?
31. What's your dream job?
32. Who is your current celebrity crush?
33. If you could be a part of a family on any TV show, which family would you choose?
34. Of all the personal questions I could ask you, what's one you wouldn't want to answer?
35. What's your biggest pet peeve when it comes to social media?
36. Who's your favorite fictional character and why? (it could be from literature, film, games, anime… you name it!)
37. What's an activity that you do not find fun at all? Why?
38. What's the weirdest thing you've ever done for a job?
39. What’s the most recent thing in your internet search history? (Explain yourself if you have to.)
40. What’s the last thing in your phone that you took a screenshot of?
41. What's your favorite color to wear? And what’s one color you’d never wear?
42. What's your favorite type of dessert? What about your least favorite?
43. What's the worst lie you ever told as a kid? Why did you tell it?
44. Who in your family are you closest to? What does that person mean to you?
45. What's your favorite sport to play and why?
46. If we were in the middle of a zombie apocalypse, who are three people you'd want by your side?
47. If you were an ice cream flavor, what would it be and why? (You can also create your own dream flavor.)
48. What's your favorite song to sing in the shower and why?
49. What's one thing your parents don't understand about you?
50. If you had a kid, what would you name them and why?
51. What are your Big Three (moon, sun, and rising) in astrology?
52. What are your feelings on astrology overall?
53.You’ve just walked into a shopping mall. Where’s the first place you’re going?
54. What's your favorite way to spend a day off?
55. What's a skill you'd love to learn?
56. This or that: Living by the sea or living in the mountains?
57. What do you want your funeral to be like?
58. What’s a tattoo you want to get and why? Name the first one that comes to mind.
59. Go to your settings. What app do you spend the most time on?
60. What do you think the No. 1 most important quality in a friend is?
61. What’s an unpopular opinion you have that you actually feel really strongly about?
62.What’s the biggest deal breaker for you in a friendship or relationship?
63. What's your favorite thing about your hometown and why?
64. What's your least favorite thing about your hometown and why?
65.What's the most moving compliment you've ever received?
66. What's your favorite way to celebrate your birthday?
67. Do you have any phobias?
68. What was your first-ever concert?
69. Who was your first favorite musical artist?
70. If you could have a job just for a day, what would it be and why?
71. What's your favorite type of movie snack?
72. What’s your favorite piece of random trivia? You can only choose one.
73. What's the best decision you've ever made?
74. What's the most important lesson you've learned from a mistake?
75. Do you have a favorite podcast? What is it and why do you love it?
76. What's the best vacation you've ever been on?
77. What's your favorite memory from the past year?
78. What's your favorite thing about your best friend(s)?
79. What's your favorite way to volunteer?
80. You’ve just been granted a treat-yourself day with three wishes. What are they, and how are you spending the day?
81. What’s the last new thing you learned? It can be a skill or a fact.
82. What’s the worst first date you’ve ever been on? Retell the story dramatically.
83. What character do you love to play as in Mario Kart and why?
84. What's the most spontaneous thing you've ever done?
85. If you could live in any fictional world, which one would it be and why?
86. What's your favorite conspiracy theory and why?
87. If you could instantly master any instrument, which one would you choose?
88. What's the most unusual talent you have?
89. What's the most interesting class you've ever taken?
90. What's the most bizarre coincidence that's ever happened to you?
91. If you could live in any country for a year, where would you go and why?
92. If you could be a fly on the wall, where would you land and why?
93. What's the best prank you've ever played on someone?
94. If you could design a theme park, what would it be like?
95. What's the most out-of-character thing you've ever done? Why did you do it?
96. What's a beloved, unusual tradition in your family that you’d want to pass down?
97. What's the best gift you've ever received? Why did you love it so much?
98. What's the worst gift you've ever received? Why did you hate it so much?
99. What's the weirdest superstition you secretly believe in?
100. What movie has made you laugh the hardest and why?
101. What movie has made you cry the hardest and why?
102. What's your greatest guilty pleasure, and when did you discover it?
103. If you could instantly be an expert in one subject, what would it be?
104. If you could have any fictional character as a best friend, who would it be and why?
105. You’re writing your will. What are you leaving and to whom?
106. If you could relive one day of your life, what day would it be and why?
107. If you could have any artist, dead or alive, perform at your next birthday, who would it be?
108. What's the funniest thing you believed as a child?
109. If you could live in any house from a TV show or movie, which one would you choose?
110. If you could have any one item of immense value in your home, what would it be?
111. If you could swap lives with any historical figure, who would it be?
112. What weird combination of foods do you secretly love?
113. Do you believe in ghosts? Explain your answer.
114. Do you believe in the afterlife? Explain your answer.
115. What’s your favorite fun fact about an animal?
116. If you could become an animal, which one would you be and why?
117. If you won the lottery today, what’s the first thing you would do?
118. Who would be on your spoil list if you won the lottery?
119.Do you believe in magic? Why or why not?
120.If you could turn any hobby into a profession, what would it be?
121. If you could create your own podcast, what would it be about, and who would be your first guest?
122. You were just handed a free one-way airplane ticket to any destination of your choosing. Where are you going? Who are you taking with you? (You can also pick solo.)
123. What’s the best thing you’ve ever found at a flea market, antique store, or yard sale?
124. Which two celebrities do you secretly (or not so secretly) love and hate, and why?
125. If you could only eat one food for the rest of your life, what would it be and why?
Bonus: Flirty 21 Questions to Ask Your Crush
These intimate 21 Questions game questions work especially well for a love interest, since they're all a little on the romantic side (and some are even a little NSFW). If you're playing with your crush or on a first date, consider these flirty questions your go-to.
1. Do you believe in love at first sight?
2. What was your first kiss like?
3. What was your best kiss like?
4. What was your first impression of me?
5. Someone just asked you on your first date. Where do you hope they are taking you? Where would you take them?
6. What are three things you are looking for in a partner?
7. Both positive and negative, what lifestyle choices are non-negotiable for you in a partner?
8. Have you ever experienced true love?
9. What fictional character have you had a crush on?
10. What are your most frequently used emojis in text conversations when you're flirting?
11. What's the wildest thing you've ever done to get someone's attention?
12. What's your biggest fear when it comes to relationships?
13. What's the most embarrassing thing you've ever done in front of someone you like?
14. Do you find first dates fun or stressful? Why?
15. What's your favorite movie couple and why?
16. If you could live out a rom-com, what would it be and why?
17. What's your favorite place to take a significant other?
18. Whose relationship do you admire and why?
19. At what point in a relationship do you think it's time to go public on social media?
20. What's your biggest turn on?
21. What's your biggest turn off?
22. What's your favorite thing about me?
23. What was the last flirty text you sent?
24. What's the worst thing about being single?
25. What's the best thing about being single?
26. Would you consider yourself a hopeless romantic? Why or why not?
27. At this point in your life, would you prefer a casual relationship or a serious relationship?
28. What's the hardest part about being in a long-term relationship?
29. What's the best part about being in a long-term relationship?
30. You’re getting married tomorrow, and you have to have a themed wedding. What theme are you choosing?
31. What's your biggest regret when it comes to a past relationship?
32. What's your favorite way to get over a breakup?
33. What meme best represents your life right at this moment?
34. Would you rather love and lose, or never love at all?
35. After a disagreement, do you initiate the makeup conversation or wait for your S.O. to?
36. How many people have you said "I love you" to in a romantic context?
37. What's the silliest excuse you ever used to get out of a date?
38. What's the most romantic thing someone has ever done for you?
39. What's the most romantic thing you have ever done for someone?
40. What's your definition of a perfect date or a dream date?
41. If you could take me anywhere in the world right now, where would it be?
42. What would you bring on a deserted island if we were stranded there together?
43. What's the most attractive quality someone can have?
44. How do you usually flirt with someone you like?
45. What’s your love language?
46. Who was your first celebrity crush?
47. Who has been your biggest celebrity crush?
48. What's the most daring place you've ever kissed someone?
49. Have you ever had a dream about me?
50. What are your erogenous zones?
51. If we were to slow dance right now, what song would you choose?
52. What’s one thing you’d love to do together?
53. What is something that you shouldn’t but can’t help but find attractive in someone?
54. What would a perfect second date look like to you?
55. How soon is too soon to kiss someone you find attractive?
Looking for more fun games and conversation starters? Then check out our lists on Truth or Dare Questions, Would You Rather Questions, This or That Questions, Never Have I Ever Questions, Questions to Ask Your Friends, and Questions to Ask on a First Date.
