21 Questions

💡 The Best List of 21 Questions to Ask a Friend, Date, Family Member, or Colleague.

Last update: 2021-06-16

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The best list of 21 questions to ask. Free PDF resource included.

Inside this article

  1. To Get to Know Someone
  2. To Ask a Crush
  3. Questions for a Guy
  4. Questions for a Girl
  5. Funny Questions
  6. To Ask a Friend

21 questions or "twenty-one questions" is a spoken parlor game and conversation starter game. It encourages creativity, critical-thinking, and general fun. This is a game that is most commonly played between two people. And the two players play when trying to get to know one another.

The original 20 questions game originated as a parlor game where one player thought of an object. And the other players asked 20 questions to deduce what the object was. With the main player responding "Yes" or "No" to the prompts. In the 1940s, the game became a popular radio panel quiz show, "Twenty Questions." That was the first broadcast on Saturday, February 2, 1946. By the Mutual Broadcasting System from New York's Longacre Theatre. This game inspired the "21 Questions" game that we know of today.

Playing the modern 21 questions game revolves around the two players choosing 21 questions to ask one another. And then prompting each other for truthful responses to the 21 questions. It is considered a conversation starter game. And intends to begin an intellectual or thoughtful prologue between the two players.

How to Play "21 Questions" the Conversation Starter Game

To play the modern version of 21 questions, each player should pick 21 questions. The players should take turns prompting the other player with the question. And responding with honesty.

The players can choose to ask the same questions to each other or choose to ask unique questions. Both are acceptable versions of the game. The game is complete when all 21 questions have gotten asked. And with each player prompting a response. Players may choose to "pass" on the question up to two times.

Most commonly, this game is played amongst couples who are aiming to learn more about one another. This can be played on a first date or when having a private evening together. Small groups can play this game by using a ricochet or round-table style format. One person starts the round and the people in the game have to answer the questions. The person asking is considered the "game head."

Playing with two players

"Player A" and "Player B" can play together. "Player A" must ask, while "Player B" responds. And once "Player B" has responded, "Player A" must respond, too. An alternative is to have "Player A" ask all 21 questions. And have "Player B" respond to each question. Then the roles are reversed and "Player B" can ask "Player A" questions.

Point system

There are no "right" or "wrong" answers when playing this game. And there are no points. The players should play at leisure, responding with an articulate response. Groups playing this game should rotate the role of the "game head." The player asking the questions. Playing this game helps develop a bond between friends, family, or new connections.

Coming up with your own questions

When coming up with your own "21 questions," consider asking interesting questions or personal questions. Something that might act as conversation starters. These questions should be unique, personal, and make the other person think.

For example, "What's your biggest guilty pleasure?" or "When was your last serious relationship?"

Be creative. "21 questions" is one of the easiest and most fun games to play with friends. And can act as a way to spark great conversations, leading to knowing people on a deeper level. Have fun!

21 Questions List

Questions to get to know someone. Prompt these questions to your crush, friend, family member, or colleague.

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To Get to Know Someone

Questions to ask to get to know someone.

  1. What's your favorite movie?
  2. What school did you go to?
  3. Which Disney character would you be if you had to choose?
  4. Is your favorite holiday Christmas, Thanksgiving, or Halloween?
  5. What's one woman who inspired your life the most?
  6. What's one man who inspired your life the most?
  7. Name a song you could listen to over and over.
  8. What's your favorite color?
  9. What food could you eat forever?
  10. If you had to pick any career, what would it be?
  11. What's one word that describes a good friendship?
  12. If you had to be in the Olympics, what sport would you play?
  13. What product could you never live without?
  14. What's the worst situation you've ever been in?
  15. What is a sign of intelligence?
  16. What does success look like to you?
  17. Are you close with your family?
  18. What do you do for fun?
  19. What's the last thing you ordered on Amazon?
  20. Which teacher had the most impact on your personal and professional life?
  21. If you asked a family member to describe you, what would they say?
  22. Are you a morning or night person?
  23. What's your dream date night?
  24. What's your "go to" karaoke song?
  25. What is the weirdest dream you've ever had?
  26. What's the most embarrassing thing your parents found you doing?
  27. What is the worst lie you've ever told?
  28. If you had a time machine, what era would you go back to?
  29. What dream job would you have if money wasn't a question?
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To Ask a Crush

List of questions to ask a crush.

  1. What object would you save if your house was on fire?
  2. What's the sexiest number you can think of?
  3. What radio station do you listen to the most?
  4. Tell me about your craziest experience in the bedroom.
  5. What piece of clothing do you remove first? Your shirt or your pants?
  6. When you wake up in the morning, do you brush your teeth first or brush your hair?
  7. What's the most dishonest situation you've ever been in?
  8. Are you close with your family?
  9. Do you say soda or pop?
  10. What's the last TV episode you watched?
  11. If you could be any planet in the universe, what planet would you be?
  12. If you had a son, what would you name him?
  13. At the end of your life, how do you hope people will remember you?
  14. Do you have any credit card debt?
  15. If you could pick any job in the world, what would it be?
  16. Do you have any student loan debt?
  17. What's the last thing you searched on the internet?
  18. Could you live without your phone?
  19. How do you define success in a love relationship?
  20. What person do you admire the most?
  21. Would you rather write music or produce movies?
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Questions for a Guy

The best list of questions to ask a guy or a boyfriend.

  1. Where do you go when you have time off from work?
  2. What place do you consider to be home?
  3. What was your least favorite subject in school?
  4. When's the last time you were in a relationship?
  5. If I were to say the word "Google," what image comes to mind?
  6. What are you looking for in a woman?
  7. If you had a child, what would you name him or her?
  8. What is your favorite TV show?
  9. What food makes you feel the most loved?
  10. If you were at a party, would you be the quiet guy or the party guy?
  11. If you were building a relationship with someone, how would you do it?
  12. What's your favorite type of conversation to have with someone? Casual, deep, intellectual, or goofy?
  13. Tell me about a time you got in trouble.
  14. Tell me about a time your parents were proud of you.
  15. Where did you go to college or university?
  16. What person do you look up to?
  17. Did you play a sport in school?
  18. What's a situation that taught you the most in life?
  19. Do you want kids?
  20. What's the month were you born?
  21. What book author has inspired you the most?
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Questions for a Girl

Questions to ask a girl or a girlfriend.

  1. What's your dream date?
  2. What's more important to you, truth, or happiness?
  3. What are you looking for in a guy?
  4. When's the last time you were in a relationship?
  5. What's a secret talent that you have?
  6. Would you rather be on the beach or in the mountains?
  7. A dog is stranded on the side of the road. Do you save him?
  8. How do you handle stress?
  9. If you could be any animal, which one would you be?
  10. How do you know that you have a connection with someone?
  11. What do you value most in life?
  12. What's one rule you have in love relationships?
  13. If you could go on a vacation right now, where would you go?
  14. How important is good communication in a relationship?
  15. What's the best piece of dating advice you've received?
  16. What woman has inspired your life the most?
  17. How do you like to have fun?
  18. What is your greatest fear?
  19. What genre of music do you prefer?
  20. What's the last concert you attended?
  21. Are you a morning person or a night person?
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Funny Questions

Funny questions to ask.

  1. Who has invaded your privacy?
  2. How would you describe your personality?
  3. Who is the worst guy or girl you've ever been in a relationship with?
  4. How would you reply to a stranger who sneezed on you?
  5. What talent best describes you?
  6. Given the chance, would you change your gender?
  7. What are your thoughts on sex?
  8. Do you have an opinion on one night stands?
  9. Do you believe in role-playing in bed?
  10. If you only had ten dollars left, how would you spend your last dollar?
  11. Who would you sit next to on a 10-hour flight?
  12. Do you party hard or party soft?
  13. Do you believe in aliens?
  14. Luck and chance, do you believe in them?
  15. If you were a superhero, which one would you be?
  16. Which animal would you make extinct from Earth?
  17. If you could live for one more night, how would you have fun?
  18. If you could have lunch with one author, who would it be?
  19. What trend do you wish would die?
  20. What's the craziest dare that you've ever done?
  21. How would you reply to a stranger who offered to kiss your face?
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To Ask a Friend

Questions to ask a friend.

  1. What book are you reading right now?
  2. What's a story that has inspired your life the most?
  3. Are you currently dating a guy or a girl?
  4. Does your astrological sign fit you?
  5. How do you spend quality time with your family?
  6. What category of movies is your favorite?
  7. Tell me about the most fun you've ever had.
  8. What's the last thing you put into Google search?
  9. What talent do you have?
  10. Before you go to bed, what's the last thing on your mind?
  11. What do you look for in people you want to be your friend?
  12. If you had to choose a way to die, what would it be?
  13. Do you get up early in the morning?
  14. What do you value in a guy or a girl?
  15. What's the biggest thing that causes you to stress?
  16. What one word describes the type of friendship you're looking for.
  17. How do you know when you became a woman or a man?
  18. Say we were to go on an adventure. Would you want to have a plan or let it be random?
  19. What trend do you think we should avoid?
  20. What hobby do you have?
  21. Tell me a habit that you have that you wish you could quit.

Bonus Questions

  1. Did you watch Saturday morning cartoons?
  2. How would you kill a zombie?
  3. Would you rather live in a large urban city or small town?
  4. If you had all the money in the world, what would you do?
  5. How do you define "happiness?"
  6. If you could go to any place on Earth, where would you go?
  7. If you were a dog, what kind of dog would you be?
  8. What personality traits do you want in a friend or partner?
  9. Would you rather hang out in a smaller group or a larger group?
  10. What type of restaurant do you prefer for dinner?
  11. How would you describe life?
  12. What time do you go to bed?
  13. What's the last thing you watched on YouTube?
  14. If you could be any actress or actor, who would it be?
  15. Do you have a crush on anyone?
  16. What's the craziest thing you've ever done?
  17. What pet peeve do you have?
  18. What's a secret sexual fantasy you have?
  19. If you could own any three cars, what would they be?
  20. What would your dream house look like?
  21. What is your favorite pet?
  22. Where's the last place you went on vacation?
  23. If you had a song on the Billboard 100, what would it be called?
  24. Who's the biggest influence on your life and decisions?
  25. What's the silliest pick-up line someone used to get your attention?
  26. Do you volunteer anywhere?
  27. If you go to a restaurant, and they have terrible service, what do you do?
  28. What's your biggest regret?
  29. What would you call your biggest mistake in life?
  30. What’s your ethnicity and background?
  31. What's the best childhood memory that you have?
  32. If you could do anything for work, what would it be?
  33. What do people think about you that's absolutely untrue?
  34. When was your first kiss?
  35. How would you survive a zombie apocalypse?
  36. If you had a secret identity, what would your name be?
  37. What's the last piece of celebrity news you were enamored by?
  38. When's the last time you were in a long-term relationship?
  39. What's the weirdest thing you do on a regular basis?
  40. How would you get your crush's attention?
  41. What's the last "sexy dream" you had?
  42. What's something that not everyone knows about you?
  43. What is the most spontaneous thing you've ever done?
  44. What's your favorite song to dance to?
  45. What's your favorite food to eat on a hot summer day?

Free Resource

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Created by John Smith and reviewed by Patrick D., the gaming guys. We love games and questions that inspire conversation. See more on the about page.