The 21 Questions Game – 105 Questions You Can Ask

by Harini Natarajan

Hanging out with your group and want a simple yet fun game to keep everyone entertained? The 21 questions game is the perfect option for you. These questions are not only fun but also give you a lot of insight into the person, including their dreams, hopes, and values. If played right, this game can be really entertaining and interesting. We have compiled a list of awesome questions for the 21 questions game. Scroll down and get started.

How To Play This Game

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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.

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 it 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

1. Dating Questions

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Finding out about your love life and date secrets can light up the mood of the party. Here is a list of 21 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?

2. Random Questions

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This the list you will want as a miscellaneous card. These 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. What is your favorite thing to do on your phone?
  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. Which cuss word do you use when you are annoyed?
  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 the thing that you would not leave your house without?

3. Naughty Questions

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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. Did you ever try to seduce anyone?
  2. What is the bravest thing you did in public?
  3. What is the thing you would do during your honeymoon?
  4. Did you ever spend a night with your blind date?
  5. How was your first kiss?
  6. When did you first see an adult film?
  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 naked?
  12. What is your experience with protection?
  13. Do you fantasize about your ex?
  14. Which was your most romantic moment?
  15. Who is the person you wanted to experience intimate moments with?
  16. Where would you want to make love for the first time?
  17. How would you describe your current love life?
  18. Who would you like to take out on a date?
  19. What would you like to gift your crush on your birthday?
  20. How would you rate your love life?
  21. Which teacher did you have a crush on?

4. Movie-Related Questions

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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 character in a movie?
  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 a 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?

5. Questions About Love Life

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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. Did you ever fall in love on the first date?
  5. Would you marry without love?
  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 any friend?
  20. What is the most romantic thing you want to do in a relationship?
  21. Whom would you choose between your best friend and your crush?

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 lesser 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 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.

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These are the best 105 questions to make the 21 questions game even more interesting. Depending on the company, you can choose any of these sets. Hope you have lots of fun while playing this game!

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Harini Natarajan

Harini has over 12 years of experience in content writing and editing for online media. She specializes in the areas of business, health and wellness, and lifestyle and is proficient in Medical Sciences (Biology, Human Anatomy and Physiology, and Biochemistry). As the Chief Editor, Harini ensures that her team delivers interesting, engaging, and authentic content. Her background in Biomedical Engineering helps her decode and interpret the finer nuances of scientific research for her team. Harini is a certified bibliophile and a closet poet. She also loves dancing and traveling to offbeat destinations.
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