Best 21 Questions Game to Ask Family & Friends (Funny & Deep)
This game of 21 questions fosters amazing conversation! They aren’t your typical questions to ask either. These are creative, revealing, and sometimes strange.
With them, you’ll get to know someone on a whole new level, and connect in a meaningful (and fun) way!
How to Play 21 Questions
First, the 21 questions game rules are nice and simple! You play with two or more people. And you can allow members to pass on questions just like with the truth or dare game. Just decide beforehand how many passes are allowed.
The game works best in small groups so that each person doesn’t have to wait too long before their turn.
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And you can play two ways:
1. One person answers the 21 questions all the way through, and then the turn goes to the next person (who answers all 21).
2. Each person answers the first question before moving on to the next question. Players take turns until everyone has answered all 21 questions.
(This is easier to keep people engaged because you are going back and forth). When you take turns like this, you can choose people at random or sit in a circle and go around the circle.
Of course, if it’s just 2 people, you’ll simply go back and forth.
100 Ideas List for This Game
Now, you will find more than 21 questions here, so that you have a variety to choose from! And follow-up questions can count too, if you are keeping track.
Do you have to ask exactly 21 questions?
No! It’s your game, so do as many or as few questions as you want!
Good 21 Questions to Ask
First, these are great questions to get to know someone, to ask a guy, a girl, or even kids!
1. What was the last photo you took?
Right away, we find out an important value or interest to the person. Is it family? Friends? Sports? Nature?
2. What is something “cool” that you think is the dumbest thing ever?
Not everything is embraced by everyone.
3. If someone made your life into a movie, what kind of movie would it be?
Drama, action/adventure, or romantic comedy?
4. In 50 years, what do you think young people will think of this time period?
Will it be seen as a time of peace, chaos, innovation, etc.?
5. What is the last thing you read?
You’ll get a feel for if the person reads the news, books, magazines, etc.
6. If you could plan any vacation to go on in three months, where would you go?
Why there and not somewhere else?
7. What do you wish parents did differently with their kids?
You’ll likely hear about a personal habit the person had instilled by his/her parents, but isn’t often taught anymore.
8. What do you wish they taught in school, but they currently don’t?
There are a lot of options here!
9. What is the best meal you have EVER eaten?
What made it stand out so much?
10. What is one memory that stands out from when you were in school?
Our past always impacts us, so find out what memory left its mark.
11. What’s the best advice you ever received?
And did you follow it?
12. If you had your own plane or boat, what would you name it?
Often, names have stories behind them, so this could be interesting!
13. What is something that you find utterly fascinating, but others think is boring?
Is it the grooming habits of monkeys? The logistics of planning an event?
14. What is your favorite holiday? Why?
You can learn a lot about someone based on their favorite family traditions.
15. Where is the most interesting place you have ever been?
Was it a museum, an architectural monument, or something else?
16. Who are the top three musicians you listen to right now?
Music moves us, so what type of music is played on the regular?
17. Which movie do you think is completely overrated?
Perhaps there are a few…
18. What do you think is the best thing about being your personality type?
Do you get things done quickly? Or maybe you get along well with others?
19. If someone gave you $1,000 to spend only on yourself, what would you buy?
The answer to this question will tell a lot about a person’s true desires.
20. What’s the worst job you’ve ever had?
And how much money would it take for you to go back to it?
21. What is your favorite way to spend a Sunday?
This will tell you a LOT about how someone prefers to spend free time.
22. How do you handle stress?
Do you go for a run? Eat a cookie? Blast the music? What gets you through?
See this great self-care ideas list if you need a healthier alternative >>
23. What is something you probably should know how to do, but you don’t?
Someday, maybe I’ll learn how to change a tire…
24. What work of art does everyone love, and you don’t understand why?
The art experts say it’s mastery, but you just don’t get it.
25. Which social media do you think needs to go away?
Facebook? Twitter? Instagram? Youtube? Which do you think does more harm than good?
Related Post:
Funny 21 Game Questions to Ask Family & Friends
This 21 questions game list is funny and fun, perfect for getting the laughs going.
26. What makes you roll your eyes every time?
There has to be something you think is ridiculous!
27. What’s the weirdest thing you’ve ever done?
Perhaps it was a spur-of-the-moment action, and later you thought “what was I thinking?”
28. If you had to give yourself another name, what would it be?
Is it close to your current name, or totally different?
29. What word is STILL really difficult for you to say?
And what word do you think is super fun to say? Try these funny tongue twisters for ideas.
30. What is the weirdest thing that you’ve seen happen at school/work?
Crazy stuff can happen around others!
31. What is a childhood memory that still makes you laugh?
What memory still gets you to smile today? Why is it so funny?
32. What game have you spent the most time playing?
What’s that one game you couldn’t seem to put down?
33. What’s the dumbest thing you’ve seen someone get upset about?
And was it you that got upset?
34. What is a food that most people love, and you think is gross?
Are you that crazy person who doesn’t like chocolate?
35. What’s the last song you sang in the shower?
Was it a new hit or an old classic?
36. What’s the worst advice you ever received?
And why do you think the advice was all wrong?
37. What is your most embarrassing injury?
We all have at least one ugly fall or clumsy event in front of others.
38. Would you survive a zombie apocalypse?
Really though, would you be the first to go? Or the last to go?
39. What fictional character or movie character have you wished you could be?
I spent a bit of time wishing I was Hermione Granger growing up, if only I could pronounce her name correctly…
40. What do you think we would do if the internet suddenly seized to exist?
Would it be total chaos? How lost would we be?
41. What is the most embarrassing purchase you’ve ever made?
Everyone has at least one! And did you use it?
42. When did you believe something or someone when you probably shouldn’t?
We can all be a little gullible sometimes…
43. What is the worst gift you ever received?
Is it that ugly sweater stuffed in your closet?
44. What’s the craziest thing you’ve ever done?
And do you regret it? Or did it turn out awesome?
45. If you had to jump into a pool of something other than water, what would you want it to be?
Chocolate, jello, or something else?
46. Would you describe yourself as naughty or nice?
Would others describe you the same way?
47. Have you ever eaten the forbidden dessert and then blamed it on someone else?
To this day, no one knows where that candy bar went…
48. If you HAD to time travel to another year, what year would you go to?
Would it be close to now or far back? Past or future?
49. What are three things that make you laugh most?
Now, this gets to the heart of what makes a person feel playful.
50. If magic were real, what would you want to do first with it?
Hasn’t everyone thought of this at least once?!
Related Posts:
- Big List of Funny Questions to Ask Anyone
- Mind Blowing Questions To Ask Friends
- Fun Conversation Games For Kids & Adults
Flirty 21 Questions Game for Couples
Flirty and maybe a little freaky make up these fun couples’ questions.
51. When do you feel most connected to your partner?
At what moments of the day/week do you feel like your relationship thrives? This tells you a lot about what you enjoy and what’s working.
52. What do you consider to be romantic?
Everyone has a slightly different version of what romance looks like. It’s important to find out!
53. What’s the best trip we’ve ever taken together?
What made it so amazing? Would you do it again?
54. If you couldn’t have both, would you choose looks or intelligence in a partner?
And is there ever a time that your answer would change?
55. If your partner turned into an animal, what animal would he/she be?
Is he/she fierce like a tiger or sweet like a koala?
56. If you had to move somewhere, where would you want to move?
Do you think you would be happier living there than here?
57. How many times have you been in love?
If he/she answers 20, you might be in trouble!
58. Do you like being surprised?
And what do you enjoy being surprised with?
59. Do you believe in love at first sight?
Is it possible to “know they are the one” right away?
60. Do you believe in soulmates?
And what does the word “soulmate” really mean?
61. Do you consider yourself an optimist or a realist?
Are you more hopeful or more practical? Or perhaps a little of both?
62. Do you believe in fate or personal choice?
Did we meet by coincidence or a grand plan?
63. What is a little white lie you’re ok with your partner telling you?
Some things are better not to know…
64. Is there a goal you’d love for us to achieve together in the next year? Or five years?
What are your hopes for our future together?
Related: Couples Vision Board Examples
65. If you had to eat a bug, what bug would it be?
Are you an ant eater, cricket lover, or beetle enthusiast?
66. What scares you most?
Find out a person’s innermost fears.
67. Which one of us would be more likely to haunt the other as a ghost?
Probably the feisty person will be picked here!
68. What is the best kiss you have ever had?
And what made it so special?
69. What do you find to be sweet about your partner?
It could be a personality trait, regular selfless action, or even a story.
70. What do you find to be sexy about your partner?
Find out what your partner likes!
71. What is one thing you will never do with me?
As in, I will never go to the hardware store for fun with my husband…
72. What is one thing you hope we never stop doing?
This gets to the heart of what someone loves about the relationship.
73. If I got a tattoo, where would you want me to put it?
And what would you want it to be?
74. What makes a relationship amazing?
Or even extraordinary? This is very open-ended and meant to dig into what each person is searching for.
75. What is one thing you need in a relationship that other people may not?
Perhaps you require more communication, space, touch, etc. than most. It’s a great thing to be open about!
Related Posts:
- Exciting Would You Rather Questions for Couples
- Epic Couples Challenge Questions
- Debate Topics For Couples To Discuss
Keep going for the free printable!
Hard Questions That Are Deep
Finally, these make you think and are good 21 questions to ask a friend or family member when you want a more meaningful conversation.
76. What do you consider the happiest moment of your life?
What kind of moment would you have to have to top that?
77. If you had to pick one cause to put your heart and soul into, what would it be?
There will most likely be a personal story behind this answer.
78. What is something that some people don’t understand about you?
We are all a little misunderstood and quirky sometimes. It’s what makes us unique.
79. If you found out you were going to die in exactly one week, what would you do with your time left?
One week isn’t much time, so only the important things remain.
80. Who is your hero?
Finding out who someone admires tells a lot about a person’s values.
81. If you could have dinner with anyone in the world (dead or alive), who would it be?
What makes this person your choice? And what questions would you ask that person?
82. What is an addiction you know you have?
Video games, sugar, caffeine…it could be a lot of things.
83. What is something you generally don’t tell people because it seems weird?
Is there anything about yourself or your life you keep to yourself? For example, I LOVE meditation, but I don’t share it often because some think it’s woo-woo.
84. What scary risk did you take that actually panned out?
You have to take a little risk to get the reward…
85. Do you have any fears that are irrational?
Anything out of the ordinary that gives you anxiety?
86. What is the best gift you’ve ever received?
This answer will give you a story and tell you a lot about the type of gift a person values. It’s also often something that was meaningful because of the context.
Here’s my favorite Christmas gift >>
87. If you could eradicate one disease from the face of the planet, what would it be?
This one is highly personal, and you’ll learn about a person’s history and family.
88. If you forgot your true age, what age do you think you would be?
Are you 25 or 85 based on your thoughts and actions?
89. What do you think is a huge problem in our society, but no one talks about it?
There are a lot of problems that we sweep under the rug. What do you think is the biggest?
90. Do you think people will live better or worse lives in the future?
Given all of the factors, will our grandchildren have a better quality of life?
91. What are three items on your bucket list?
Those top three tell you a TON about the type of life someone wants to live.
92. If you could do 1 thing off of your bucket list today, what would it be?
Now, given those items, which one is the most important? Or possibly the most reachable? Why not do it today?
93. Where is one place you hope you never have to go?
This will tell you about what someone believes is a really bad environment.
94. When was the last time a “red flag” or alarm bells went off in your head?
Did you listen to the red flag? What happened?
95. What is something you have learned with age?
Are you wiser now than you were five or ten years ago?
96. If you could find out the truth about one life mystery, what would it be?
Would you get to the heart of a conspiracy theory, a mystery of the universe, or something else?
97. What has been your hardest habit to break, and you are really proud of doing it?
And did it take you long to break it? How did you do it? Share your wisdom!
98. Would you want to be buried or cremated at the end of your life?
Would you want your organs to be donated?
99. What are the five things you are most grateful for in your life?
Are any of them a surprise? Are these things you’ve always been grateful for?
100. How do you hope people remember you when you die?
What’s the legacy you wish to leave?
Related Post:
21 Questions Free Printable
Then, print the free pdf printable below with examples from the post!
Grab more like this:
Fun Game Variations
The classic 21 Questions game is a fun way to get to know someone better. But you can also spice it up with the ideas below:
Truth or Dare 21 Questions Game
Players use these questions as the truth option. Find great ideas for kids dares if they choose a dare.
Never Have I Ever 21 Questions
In this variation, players take turns asking each other 21 questions, but instead of asking a question, they say “Never have I ever…” and complete the sentence with something they have never done.
*Never have I ever family friend ideas >>
21 Questions: Rapid Fire Edition
Set the timer for 30 seconds or a minute and players must answer within the agreed upon time limit. This variation adds excitement to the game.
*Rapid Fire Questions For Kids & Adults
Would You Rather
Add a decision-making element to the game by making players choose. Players take turns asking each other “Would you rather…” using the 21 question ideas. This variation leads to interesting discussions and debates.