The 21 Questions Game: 137 Fun, Formal, and Flirty Things to Ask — Best Life (2024)

These topics will take your game to places casual conversation would probably never go.

Have you ever wanted to take a conversation from small talk to those deeper questions but weren't sure how to get there? You're not alone, and there are no advanced communication skills needed. Sometimes, all that's necessary to provoke some invigorating conversation is a game, like 21 Questions. Below, we've collected a series of prompts on various topics you can use the next time you play, whether that's with colleagues, friends, or family members. Read on to get started!

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How Do You Play the 21 Questions Game?

It's a classic game, and the rules are simple: One person in the group will be put in the hot seat while the other players take turns asking them questions. The number of turns awarded to each person depends on the size of the group, but the round will come to an end once the 21st question is asked and answered.

For the most successful outcome, you might want to suggest the most outgoing member of the group go first. While the game is meant to be simple and lighthearted, being the first person up can come with a lot of pressure, and some people might cope with it better than others.

The more time that goes by, the easier it will be for the more reserved members of the group to loosen up—and that can only make gameplay more fun. After all, the goal is to have everyone answer the questions asked of them as candidly and honestly as possible.

If you want to make things a little more interesting, you can create some kind of point system. Answering harder and more personal questions will score you more points than easier items from the list. Whoever answers the most questions and collects the most points by the end of the game "wins."

What's the Point?

Not only is the 21 Questions game a fun way to pass time with friends, but it's also a great icebreaker for interacting with folks you don't know all too well. Whether you're mingling with strangers or looking for conversation starters to use at work, this question-and-answer format can make meeting people a whole lot less awkward.

Think about it: Games keep you on track. You can't get tangled up in small talk when you're trying to accomplish something specific. This structure allows you to reveal truths about yourself and learn the same from others without having to justify yourself or even provide much background.

It also stretches the boundaries of what kind of information can be put on the table. Will you have the opportunity to discuss the weirdest thing you've ever put in your mouth during casual coffee talk? Probably not. But during a game of 21 questions? You bet.

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21 Questions Game Ideas

21 Questions is a simple and fun game and it's a surefire way to get to know the people around you. Check out our list of questions for some inspiration before you begin!

Flirty Questions for Your Crush

1. Do you enjoy being single or do you want to find a serious relationship?
2. What's the craziest thing you've ever done on a first date?
3. Do you believe in love at first sight?
4. What's the weirdest thing you've ever put in your mouth?
5. What's your most R-rated guilty pleasure?
6. How would your friends describe you?
7. Why did your last relationship come to an end?
8. When was the last time you watched an adult movie?
9. What's your biggest turn-on?
10. When was the last time you had a sexy dream?
11. What's your love language?
12. Describe your best kiss.
13. Describe your dream date.
14. Have you ever had a dream about me?
15. What makes you swipe left on someone immediately?
16. What makes you swipe right on them, then?
17. Are you a morning person or a night person?
18. What's the silliest pick-up line you've ever used on someone?
19. What was your first impression of me?
20. Do you prefer a wild night out or a quiet night in?
21. Who is your celebrity crush?
22. Do you snore?
23. What would you do if I called you in the middle of the night?
24. What's your biggest turn-off?
25. What's your favorite place to go to with a significant other?
26. Do you think first dates are more fun or more stressful?
27. What was the last flirty text you sent?
28. When dating someone new, do you prefer to hang out one-on-one or in a group setting?
29. What's the most spontaneous thing you've ever done on a date?
30. Would you prefer a long, warm hug or a passionate kiss?

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Random Questions to Ask

31. What is the weirdest dream you have ever had?
32. What's your favorite song?
33. Are you a vegetarian?
34. What's your favorite movie from the past year?
35. What was your most embarrassing moment at work?
36. How did you meet your best friend?
37. Are you a good driver?
38. If you had a time machine, what era would you travel back to and why?
39. What's a bad habit that you're trying to break?
40. Who was the last person you're guilty of double texting?
41. What's your go-to karaoke song?
42. Do you consider yourself a punctual person?
43. Under what conditions would you absolutely not be able to fall asleep?
44. How would you describe your personal style?
45. In what ways are you messy or disorganized?
46. How long does it typically take you to fall asleep?
47. If you could soak up all the knowledge that exists around one subject, what would it be?
48. What's your biggest fear when it comes to traveling?
49. What's your favorite TV theme song?
50. Kittens or puppies?
51. When was the last time you had strep throat?
52. What's the oldest article of clothing you own?
53. Do you have a green thumb?
54. Do you know how to work a grill?
55. Are you superstitious?
56. What was the most surreal moment you've ever experienced in real life?
57. Who is your favorite character from a movie?
58. Have you ever hitchhiked?
59. When was the last time you finished a puzzle?

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Interesting Questions for the Workplace

60. Can you describe your dream job?
61. What's the next item you want to cross off your bucket list?
62. What's your favorite food?
63. If you could give your younger self one piece of advice, what would it be?
64. What's your dream destination for your next vacation?
65. What's your favorite sport?
66. Describe your typical before-work routine.
67. What energizes you at work?
68. Do you like to make plans for after work or do you like to go right home?
69. How would you feel about more team happy hours?
70. If you had the option to bring your pet into the workplace would you?
71. How do you commute to work?
72. If you weren't working in your current department, what's one area of the company that you would like to explore?
73. What's one thing you're currently trying to make a habit of?
74. What was your first job?
75. What's your favorite sports team to root for?
76. If you could only keep three apps on your smartphone what would you pick?
77. What's your favorite place to eat around the office?
78. What's something that surprised you about the company after working here?
79. What did you like to do during recess?
80. Is there any experience that you think everyone should be required to have?
81. Do you have any book recommendations for the rest of the team?
82. Do you have any hobbies?
83. What kind of activities drain you?
84. How do you like your day to end?
85. What was your favorite subject in school?

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Personal Questions for Couples

86. What's the biggest lesson you've learned from your past relationships?
87. What's your idea of the perfect date?
88. How old were you when you had your first kiss?
89. What are three qualities you think are imperative to a healthy relationship?
90. How many times a month do you think we should do date night?
91. When you think back to all the years we've spent together, what's your favorite memory that comes to mind?
92. What's your favorite childhood memory?
93. What's your biggest regret?
94. If money weren't a factor, how many kids would you want to have?
95. What's one family tradition you grew up doing that you would want to recreate down the line?
96. If you had three wishes that would come true, what would they be?
97. Who are you most envious of?
98. What's one thing you've done in past relationships that you wouldn't do today?
99. What's one thing you've always wanted to try in the bedroom but never had the courage to ask for?
100. Do you see yourself always living here?
101. What's your favorite quote?
102. Have you ever texted someone a nude photo of yourself?
103. Is cheating an immediate dealbreaker for you?
104. What do you think about ethical non-monogamy?
105. What do you think is your strongest contribution to this relationship?
106. Outside of sex, what's the most intimate activity a couple can do together?
107. If you could change one thing in your life, what would it be?
108. How many people have you said "I love you" to in a romantic context?
109. What's the hardest part about being in a long-term relationship?
110. Would you want to write your own vows if we were to get married?
111. How do you feel about girls' trips/boys' trips?
112. If you could have one more conversation with your ex, what would you want to ask them?

RELATED: 250 "Would You Rather" Questions That Are Impossible to Answer.

Unexpected Funny Questions for Your Friends

113. What is the most embarrassing thing you've done in public?
114. What's your biggest pet peeve and does anyone here violate it often?
115. What's one place where you can always bet on having terrible service?
116. Can you describe your dream house?
117. What's your favorite Bob Odenkirk role?
118. How would you try to survive a zombie apocalypse?
119. How often do you engage in solo intimate moments?
120. Do you have a secret identity?
121. What's the worst lie you've ever told?
122. When you listen to music, do you hear the sounds or the words?
123. Do you like your water ice cold or at room temperature?
124. Has anyone ever had a hard time pronouncing your name?
125. If you had to dye your hair another color what would you choose?
126. What's the best WiFi network name you've ever seen?
127. Have you ever fallen off your bike in front of a big crowd?
128. How do you hang your toilet paper: Over or under?
129. Have you ever stolen something small like a candy bar from the corner store?
130. If you went to college, what was the most useless class you took?
131. What do you want your next hairstyle to be?
132. What's the weirdest lie your parents ever told you?
133. Did your mom ever cut your hair as a kid?
134. Has anyone ever caught you talking to yourself?
135. If you could describe the perfect night out in one word, what would it be?
136. What's the most useless way you like to spend your free time?
137. What's the worst excuse you've ever used to get out of an awkward situation?

Wrapping Up

That's all we have on the 21 Questions game, but be sure to check back with us soon for even more fun.

Carrie Weisman

Carrie Weisman oversees all SEO efforts at Best Life. She specializes in content optimization and editorial marketing.Read more

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