21 Questions Game – 211 Questions To Ask And How To Play

Ask away to know the general, personal, and naughty details that make ice-breaking fun.

Reviewed by Roma Williams, LMFT Roma Williams Roma WilliamsLMFT facebook_iconinsta_icon
Written by , Integrated MA, Certified Relationship Coach Sneha Tete Integrated MA, Certified Relationship Coach linkedin_icon Experience: 4 years
Edited by , MA (English) Subhrojyoti Mukherjee MA (English) Experience: 4 years
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The 21 questions game will keep everyone amused when you are out together. There is no end to the topics you can choose to ask questions from in this simple and fun game. You can come up with numerous quizzes or guessing games on various topics, like pop culture, movies, music, sports, television, and more, which you can use as a conversation starter or icebreaker in a group setting. In addition, you can learn a lot about the participants through these questions, such as their aspirations, hopes, and values. Thus, it can be entertaining and insightful if you play it right. Check out these awesome questions we have come up with for the 21 questions game. Then, start playing and have fun!

protip_icon Trivia
The 21 questions game differs from the classic 20 questions game, which focuses on asking questions to guess an object. In contrast, the 21 questions game is about getting to know each other better.

How To Play This Game

How to play 21 questions game
Image: Created with Dall.E

This is the easiest of all games, and the only rule you need to follow is to answer the questions with honesty. The game can be played with two or more players, irrespective of age or gender. Each player has to answer a set of 21 questions.
To make things more interesting, the players can divide the questions and allocate points to each. The person who answers them all wins.

If you gather more than two people to play, all the other players get to ask you a question from the list as per their wish. The cycle of questions can continue with the last person answering starting the next set of questions.

protip_icon Quick Tip
Since the 21 questions game is played in groups, you can use a dice to determine the order of the sequence. Each person rolls the dice, and whoever has the lowest number goes first, and so on.

Echo Style Of Gameplay

Another way to play this game would be to change the pattern of questions. Say, A asks B a question, B has to ask C another question after answering A’s question. This way, everyone gets to ask different questions, and it does not get repetitive and monotonous.

The best part about the game is you can keep changing the rules. All that matters is having the time of your life with your friends.
Remember, these questions may lead to stories, and in case a person starts relating an incident after answering the question, do not interrupt. The whole idea behind the game is to have tons of fun with your buddies.

Let’s get started!

The 21 Questions Game

Dating questions are great when you want to know someone but in a fun way. These simple games do not have any competition; they are all about entertainment and knowledge about your partners.

1. Dating Questions

Ask questions about the love life of your partner on the date as part of 21 questions game
Image: Shutterstock

Finding out about your love life and date secrets can light up the mood of the party. Here is a list of fun and insightful questions related to dating:

  1. Have you ever dated anyone way older than you?
  2. What was your most romantic date ever?
  3. How important are looks to you?
  4. What would you choose – ugly but smart or beautiful but dumb?
  5. What gets you nervous on dates?
  6. Did you fall in love with someone you went out on a blind date with?
  7. Of all the people you have dated, whose voice do you like the most?
  8. What was the most daring thing you did on a date?
  9. Did you ever experience rain on your date?
  10. What was the one thing your partner said that you would never forget?
  11. If the person you date offers to take you to someplace alone, will you go?
  12. What, according to you, is a perfect date?
  13. If you had superpowers on your date, what would you wish for?
  14. What is the sexiest thing you wore on a date?
  15. If the perfect guy asked you to marry him on the first date, what would you do?
  16. What would you like your date to be dressed in?
  17. How would you want to propose to your crush?
  18. Which would you prefer – online dating or offline dating?
  19. What was the most expensive thing you ordered on a date?
  20. What is the best thing you received on a date?
  21. If your favorite celebrity asked you out, what would you do?
  22. What is your backup plan if everything you planned for the date goes wrong?
  23. What makes you swipe right on someone’s dating app profile?
  24. Would you ask someone you just met to be your +1 at a wedding?
  25. What do you think is absolutely unacceptable on a blind date?
  26. What is the most embarrassing thing you have done or said on a first date?
  27. Have you ever ghosted someone or been ghosted on a first date?
  28. What topic is an absolute turn-off on a first date for you?
  29. What if they are a 10, but wear the most outrageous outfits wherever they go?
  30. What if they are a 10, but talk with food in their mouth or chew loudly?
  31. What would make you ask someone out on a second date?
  32. What is an instant sign that there won’t be a second date?
  33. How would you politely decline the offer of a second date if you are not interested?
  34. Would you, being the reserved, silent one, date someone who filled in the silence by only talking about themselves?
  35. Would you date one of your close friend’s exes from several years ago?
  36. What similar qualities that you and your date share would ensure a smooth dating experience for you?
  37. How do you feel about long-distance dating?
  38. Would you prefer a serious and intimate dinner or a playful and fun workshop/activity for a first date?
  39. Would you date your siblings’ friends?
  40. Would you take your date to a place you and your ex frequented?
  41. At what point in the dating phase would you feel comfortable introducing a date to your friends?
  42. What would make you feel things are moving too fast for comfort?

A blogger shares the joy of hosting virtual trivia nights, offering a diverse set of trivia questions ranging from general knowledge to pop culture, perfect for FaceTime or Skype gatherings during lockdown. She expresses the fun and uplifting impact of these trivia nights, stating, “This has become the thing we look forward to each week as we wait for life to return to normality and has been so great for lifting the spirits! (i)”

2. Random Questions

If you are bored and you have nothing to do with a bunch of people in your room, play this game. Random questions game gives you the liberty to pick a range of topics, like celebrities, current events, history, geography, science, literature, and much more.

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This is the list you will want as a miscellaneous card for party games. These trivia questions don’t follow a theme but will help you keep the game interesting and know your friend better.

  1. What would be the first thing you would do if your flight was delayed and you sat beside a handsome person in the waiting lounge?
  2. If you run into your celebrity crush, what would you do?
  3. If you hit the jackpot, what would you do with the money?
  4. Who is your favorite person to hang out with?
  5. What would be your “never have I ever” question?
  6. What would you name your autobiography?
  7. If you were asked to stay back for work at Christmas, what would you do?
  8. What would you do if you found out your crush was going to be your co-passenger?
  9. What tops your wishlist?
  10. Would you rather know your future or your past?
  11. Would you rather live in a beach house on an island or live in a cozy cabin in a forest?
  12. If you were given a time machine, what would you do?
  13. What do you do when you are stressed?
  14. What is your best pick-up line?
  15. At what point would you like to restart your life?
  16. How do you make up to your best friend after a fight?
  17. What is the best thing you like about you?
  18. If you get hurt, how would you react?
  19. What are your three things to do before you die?
  20. Who is your biggest inspiration in life?
  21. What is one book that you read a long time ago but still think about?
  22. What is your idea of a good friend?
  23. What is your favorite adventure activity and why?
  24. What is an unforgettable memory from your childhood?
  25. What was the weirdest thing you believed as a child?
  26. When you were a child, what did you want to grow up to be?
  27. How did you and your friends have fun as children?
  28. What is a habit or ritual that you have carried from your childhood?
  29. What does your perfect weekend look like?
  30. Do you have any interest in collecting anything, like stamps or baseball player cards?
  31. What is the most impactful thing you have heard someone say about you?
  32. What is something that you wish you were talented at?
  33. What are your thoughts on the afterlife?
  34. What are five things you always carry in your purse or backpack?
  35. Cereal on top of milk or milk on top of cereal?
  36. What is an odd food combination that you love?
  37. If you could travel to only one foreign country in this lifetime, which would it be?
  38. What is your go-to game for game nights with friends and family?
  39. What is one thing you would love to try if you didn’t worry so much about what others think about it?
  40. What are your current top five most played songs?
  41. What are your favorite lyrics of all time?
  42. If you could go back in time and meet a dead artist, who would it be?

3. Naughty Questions

These kinds of questions are often played between partners or the people you are most comfortable with, it could be about your most embarrassing moment or your hidden fantasies.

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These sassy questions will surely spice up the mood of the game. As they are bold, these questions are more fun when a whole group is involved, and your special one is a part of it.

  1. Have you ever tried to seduce anyone?
  2. What is the bravest thing you have done in public?
  3. What is a bold thing you would try during your honeymoon?
  4. Did you ever spend the night with a blind date?
  5. How was your first kiss?
  6. Who is your celebrity crush?
  7. Did you ever get caught doing something wrong?
  8. What is the bravest thing you did in a truth and dare game?
  9. Which is your best kiss moment in a movie?
  10. Which was your first adult movie?
  11. Have you ever accidentally seen anyone without their clothes on?
  12. What inspires you to make the first move?
  13. Do you fantasize about your ex?
  14. Which was your most romantic moment?
  15. What is the most romantic thing you have done for a partner?
  16. Who is the person you wanted to experience intimate moments with?
  17. Where would you want to make love for the first time?
  18. How would you describe your current love life?
  19. Who would you like to take out on a date?
  20. What would you like to gift your crush on their birthday?
  21. How would you rate your love life?
  22. Which teacher did you have a crush on?
  23. What is your guilty pleasure?
  24. Do you ever go outside without your underwear on?
  25. Would you dirty dance with a random stranger at a club?
  26. Have you ever felt attracted to someone far apart in age?
  27. Would you make the first move on your date?
  28. Have you ever tried to read smut in public?
  29. Have you ever sexted with a stranger?
  30. Have you ever intentionally led someone on, despite not being interested in them?
  31. What is the boldest way you have conveyed your feelings towards someone?
  32. What is an innocent, mindless habit in another person that you surprisingly find seductive or attractive?
  33. What is your idea of spicing up a date night?
  34. Have you ever drunk-dialed an ex?
  35. What is your most embarrassing drunk episode?
  36. What has been the single most sensuous experience of your life?
  37. If you were to play a naughty prank to set two of your friends or acquaintances up, what would it be?
  38. Have you ever pretended to be someone’s romantic partner to make someone else jealous?
  39. What are your thoughts on clothing-optional beaches?
  40. Would you go skinny dipping with strangers you met recently?
  41. What is the worst dare you ever gave someone in a game of truth or dare?
  42. What is the worst prank you have ever played on anyone?

4. Movie-Related Questions

Movies are a big part of our life. We all have grown up watching movies and questions related to movies can bring only nostalgia and fun on the table.

Image: Shutterstock

Your choice of movies defines your taste and likes in life. Here is a list of movie questions that will help you know your friends better:

  1. Which movie had a huge impact on you?
  2. Which is your favorite action movie?
  3. Which movie have you watched over 50 times?
  4. Which is the first movie you watched in a theater?
  5. Which was your first horror movie?
  6. What do you like to snack on while watching a movie?
  7. Which genre do you stick to?
  8. Who is your favorite movie character?
  9. Have you ever cried watching a movie?
  10. Do animated movies touch you?
  11. What is your favorite experience of watching a movie?
  12. Which movie did you have to watch more than once to understand it?
  13. Which TV series are you most attached to?
  14. Which movie do you like more than the book?
  15. Which movie made you like the villain more than the hero?
  16. Which movie scene would you like to recreate in your life?
  17. Which movie did you watch on your first date?
  18. Which movie character do you relate to?
  19. Which movie did you regret watching?
  20. Who is the worst person to watch a movie with?
  21. Have you ever been inspired by a negative character?
  22. What is your take on morally gray characters?
  23. Would you be able to watch a horror movie by yourself in a secluded cabin?
  24. What is a recent movie you have been obsessed with?
  25. Do you prefer watching critically acclaimed movies or underrated indie movies?
  26. What is a genre-specific trope that you can never get enough of?
  27. What is your take on the influential powers of a well-made movie?
  28. What is your idea of a well-made movie?
  29. Do you like capturing everyday moments of your life on video, making personal mini-movies for yourself?
  30. Have you ever made a birthday movie for someone? What was your process?
  31. The Marvel Cinematic Universe or the DC Extended Universe?
  32. Star Trek or Star Wars?
  33. Who is your favorite director of all time?
  34. Who are your favorite on-screen pairs?
  35. Which actor’s movies have you never missed?
  36. Do you have a movie night ritual?
  37. On a scale of 1 to 10 how frustrating is it for you to be interrupted while watching a movie?
  38. What are the top five movies you would recommend to someone without a moment’s hesitation?
  39. What is your take on Hallmark holiday movies?
  40. What are some romantic movies you would recommend for a date night?
  41. Is there a movie that you feel deserves a better ending? How would you rewrite it?
  42. Which movie remake or sequel ruined the original for you?
  43. Which movie do you think deserves a sequel?

5. Questions About Love Life

Sometimes we have to unearth our secretive love life, and give something spicy to your friends to giggle about. It could be funny moments of you and your partner or the one when you wouldn’t stop fighting for silly little things.

Image: Shutterstock

If you have feelings for someone but are afraid to make a move without being sure of what they feel about you, this is the set of questions you should stick to:

  1. Who was the first person to propose to you?
  2. Do you believe in love at first sight?
  3. According to you, what defines a perfectly healthy relationship?
  4. Have you ever fallen in love on a first date?
  5. Would you marry someone without loving them?
  6. How would you celebrate your wedding?
  7. If you had to marry a person right now, who would you choose?
  8. What is your secret to making your love life work?
  9. Which is your favorite destination for a date?
  10. How much do looks and appearance have to do with a relationship?
  11. Have you ever cheated in a relationship?
  12. Have you ever been in true love?
  13. Would you change yourself for the person you love?
  14. What kind of person would you fall in love with?
  15. What is the craziest thing you have done for love?
  16. What is the most awkward situation you have faced in a relationship?
  17. What would you choose – money or love?
  18. Were you ever obsessed with anyone?
  19. Did you ever have a crush on a friend?
  20. What is on your ‘ideal partner’ checklist?
  21. Whom would you choose between your best friend and your crush?
  22. Do you think a comparison between your best friend and your significant other is fair?
  23. How much are you willing to change yourself to accommodate a partner in your life?
  24. How important are your friends’ and family’s approval of your partner to you?
  25. Would you let your friends and family interfere or influence your relationship?
  26. Do you agree love requires a lot of work? Are you willing to put in the work?
  27. How important is sex in your love life?
  28. How important is emotional intimacy in your love life?
  29. How long would it take you to share your financial details with a partner?
  30. How important is sharing the same sense of humor in a relationship?
  31. Do you have an ex you still think fondly of?
  32. What was the most intensely romantic experience of your life?
  33. What is your idea of romance?
  34. Do you think you are romantic?
  35. Do you look for thrill or comfort in a relationship?
  36. Can you handle being with someone who snores too loudly?
  37. Can you live with someone who doesn’t share your idea of hygiene?
  38. What is the cringiest thing you have done in a past relationship?
  39. What is an immediate red flag for you in a relationship?
  40. Would you rather have a partner who says the kindest things or does the kindest things?
  41. Would you have a showdown with your partner if it was the only way of arriving at a solution?
  42. What is your love language?

While you play this game, there are a few tips to be kept in mind:

  • Be honest in your replies.
  • It is best to have fewer than 8 people in the group to keep the cycle of questions short and interesting.
  • You can make the game exciting by giving choices for the answers.
  • It is best if you play this game with people you know and are comfortable with.
  • This game is all about fun, so keep the mood light and do not get offended.
  • Do not judge anyone for the answers they give.
  • Do not interrupt anyone even if they take a lot of time to explain their story.
Image: Shutterstock

Infographic: Why Play The 21 Questions Game?

The 21 Questions Game is an easy and interesting way to get to know someone better. It is a question and answer game that you play with friends and family. You can also play it with your date and understand each others’ personalities in a fun way. This game also provides you with an opportunity to develop and build many important skills that play an important role in preparing you for life.

Check out the infographic below to know what this game has to offer.

why play the 21 questions game (infographic)

Illustration: StyleCraze Design Team

Now that you have all the required questions to play the 21 questions game, you can gather all your folks and get started. These questions are perfect for game nights, sleepovers, and random get-togethers. ‘21 Questions’ is one of the easiest questions to play, but the only catch is you have to answer the questions honestly. As mentioned before, the plan is to have fun, so do not offend anyone in the process. Along with taking inspiration from the questions above, follow the tips to make the game a success.

Frequently Asked Questions

What are some juicy 21 questions?

You may ask questions like “What is the weirdest dream you have ever had?” or “What is that one thing about yourself that you would like to change?” or ask about embarrassing encounters. However, ensure that the questions do not hurt or offend them.

What is an example of a deep question?

You may ask someone questions about life, their highest and lowest points, struggles, motivations, aspirations, and accomplishments. These will help you to understand them at a deeper level.

What are the 21 questions categories?

There are no strict categories of questions to play the 21 questions game. However, be mindful of the group dynamics and the comfort level of all the participants to ensure you do not ask uncomfortable or offensive questions. Some safe question categories are hobbies, travel bucket lists, favorite music, and funny personal stories.

How long does a game of 21 questions last?

A game of 21 questions can keep you and your friends entertained for several hours until people want to take a break or have had enough of it. As each question is unique and it is thrilling to learn more about people you like, it can keep people hooked on to it for a long time until their curiosities are satiated.

Can you only ask yes or no questions in the 21 questions game?

Not necessarily. Your questions can be detailed and require the other person to reflect on them for a while. However, if you wish, you can add your own rules to the types of questions that can be asked.

What kind of things can you use for the 21 questions game?

The 21 questions game does not require props or other things as they are simply questions to know the other person’s perspective on things.

Key Takeaways

  • 21 Questions is a simple, fun, and insightful game that helps you learn a lot about the participants.
  • The only rule you have to follow is to answer with honesty.
  • You will need more than two people to play the game.
  • Allocate points for each question and keep the questions interesting to have fun.


Learn how to play the classic game of 21 questions! Watch this video for fun tips on how to ask the right questions and enjoy with your friends.

Personal Experience: Source

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