21 Questions Game: 100+ Deep & Freaky Questions To Ask Your Crush

These freaky 21 questions to ask a girl will help you enjoy and engage in some useful conversations with your friends. We bet you would love the 21 Questions Game!

Ever heard about the 21 Questions Game? You're at the right place!

There are days when you have some free time at work and you are engaged in a fun banter with your coworkers. Do you wish to take things up a notch and have some really interesting conversations on a vast range of topics?

Well, you can play some games that involve deep conversations. Question games like Most Likely To, Icebreaker Questions, Never Have I Ever, and Would You Rather are all great games for such occasions. Another such game is 21 Questions To Ask.

In this article, we will cover:

  • What is 21 Questions Game?
  • How to play 21 Questions Game?
  • 21 questions for a new relationship
  • 21 questions to ask a girl
  • 21 questions to ask a guy
  • Freaky 21 questions game
  • 21 Questions to Ask Your Crush
  • Good 21 questions to ask

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What is 21 Questions Game?

If you want to initiate deep and interesting conversations with your friends or colleagues, then the 21 questions game can be a very good choice. You can put forth different varieties of questions related to deep thinking, interpersonal relationships, spirituality, and lots more.

Certain questions can be directed only to guys, some can be only for girls and you can add a few humorous questions too for some fun time.

This game tests your knack for keeping a conversation going and requires you to put on your thinking cap. The member answering the maximum number of questions smartly wins the game.

Read more: 25 Best Icebreaker Questions For Your Next Christmas Get Together

How to play 21 Questions Game?

how to play 21 questions

You need a minimum of 2 or more members to play this game. However, the real fun comes in when there are at least 4-5 people. If there are too many people, then the game may take longer to complete since each person needs to answer 21 questions. However, if you have sufficient time, even a 10-member gang can play this game.

  1. One question at a time: In this method, one player chooses a question and all the players need to come up with an answer one at a time. Once all members have answered a question, the group moves on to the next question. This will continue until all 21 members have answered all 21 questions.
  1. Back-and-forth questioning: In this method, the first person poses a question to the second person. After which, the second person poses another question to the first person. You can choose this method to play in case there are only 2 members playing the game. The questions can be relationship-based or couple-based. 
  1. Rapid-fire questioning: In this method, every person needs to answer all 21 questions in one go most likely with a timer. The person who answers all the questions craftily without skipping a single question will be the winner.

Now that you know everything about the game and how to go about playing it, let us check out the kind of questions that can be put forth in this game.

Read more: 13 Fun Question Games to Enjoy With Friends and Coworkers (2023 Update)

21 Questions For a New Relationship

If you have just entered into a new relationship and would like to have a deeper understanding of your partner, then you can play the 21 questions game and try posing these questions.

  1. What is your idea of a perfect date?
  2. What would be your reaction if you ever found out that I am cheating on you?
  3. Do you believe that relationships can last for a lifetime? 
  4. Are you still in touch with your ex?
  5. With whom do you share the closest bond in your family?
  1. Do you believe in the concept of Valentine’s Day or would you like to make each day special in your own way?
  2. Do you break down easily or are you emotionally strong?
  3. Do you believe we can have a strong and lovely future together?
  4. Can we inspire other couples?
  5. What made you break up with your ex?
  1. What are the ideal qualities you are looking for in your partner?
  2. Who was your first crush?
  3. Would you like to pursue any new hobby?
  4. Are you happy in your current profession?
  5. How would you spend your last day on this planet?
  1. Are you good when it comes to handling conflicts or do you tend to ignore them?
  2. Do you always want to have the last word during fights and arguments?
  3. Will you be able to give a second chance to our relationship if it ever hits rock bottom?
  4. Do you love to have some time alone?
  5. What’s your perfect idea for spending weekends?
  6. Would you like to have kids in the future?

Also Read: 100 Team Trivia Questions for Fun & Team Bonding

21 Questions to Ask a Girl

After giving guys their share of questions, how can we not give questions that girls would love to answer? Check out the list of 21 questions to ask a girl.

  1. Would you want to live like a queen or love how you are now?
  2. What would you do if you discovered a diamond ring (which is not yours) inside your purse?
  3. If you and you and your friends planned a sleepover at a friend’s place, would you love playing some interesting games or would you simply indulge in idle gossip?
  4. If your best friend and your partner cheated on you, would you forgive both of them or remove them from your life forever?
  5. Describe yourself in five words.
  6. Is there some hobby you pursued a while ago but stopped because of personal commitments?
  1. Have you ever felt let down by anyone?
  2. What is your greatest fear? Do you believe you can overcome it?
  3. What is that unique quality of yours that other girls would want to have?
  4. What are those three things that you would like to take with you to a lonely island?
  5. If you want your child to inherit something from you, what should that be?
  1. How do you choose your friends?
  2. What is your idea about your ideal man?
  3. Would you prefer an all-girls trip or would you like to have guys also in your group?
  4. What was your favorite subject while you were in school?
  5. If you ever get an opportunity to conduct research, which topic would you like to take up?
  1. What is the weirdest rumor that you have ever heard about yourself?
  2. Are you an introvert or an extrovert?
  3. If you could be a boy for a day, what would you do?
  4. Do you believe that you can have the power to change your destiny?
  5. Do you love to put on lots of make-up or prefer being simple?

Well girls, we hope you all have a good time and lots of fun answering these questions.

Read more: 10+ leadership Games to Play as a Team Building Activity at Work

21 Questions to Ask a Guy

We have prepared a list of questions exclusively for boys. If you wish to know a guy better, then you can put forth these questions to him.

  1. Would you want to be like Superman or are you happy with how you are?
  2. Do you hate studying and writing exams or would you like to increase your knowledge?
  3. If you are given a choice between a Lamborghini Aventador SVJ and a Kawasaki Ninja H2R, which one would you pick?
  4. How do you spend your free time?
  5. What do you love doing on weekends?
  6. Would you prefer to go out with your parents for dinner at your favorite restaurant or catch your favorite show on TV?
  7. Choose any one option: cycling, hiking, or trekking.
  8. Have you ever idolized anyone?
  9. If there is something you want to let the world know about you, what is it?
  10. If you had a choice between traveling to your favorite holiday destination with your family and a road trip with your friends, what would be your choice?
  11. What is that one thing which you always procrastinate?
  12. What is the most adventurous thing you would like to do at least once in your lifetime?
  13. Would you love to develop a useful mobile application or would you want to invent a useful gadget?
  1. Name one thing in which you are a genius.
  2. When was the last time you cried?
  3. Have you ever made any tough decisions in your life? If yes, then what are those?
  4. Do you sleep with your mouth open?
  5. Are you a heavy sleeper or tend to get up at the slightest possible noise?
  6. Would you prefer to have a pet tiger or a pet wolf?
  7. Are you thoroughly enjoying your professional career or wish you had taken up something else?
  8. Choose any one of these - skiing on snowy slopes or driving on mountainous terrains.

Also Read: 250 Random Questions to Get Better Acquainted With Your Coworkers

Freaky 21 Questions Game

Would you like to have a freaky, or rather scary question-answer session (albeit in a funny way)? Then have a look at these questions below. They can send a chill down your spine and also tickle your funny bone at the same time.

  1. What is the scariest dream you have ever had?
  2. Will you spend a full night all alone in a haunted hotel or walk through a graveyard alone at night?
  3. You are visiting an under-construction building. All the laborers have left and you are the last one to leave. You get into the lift all alone and start coming down. Due to some malfunctioning, the lift suddenly stops and you have no one to call for help. What will you do?
  4. If your house is on fire and you have the time to take only three things with you, what would you take?
  5. What’s the craziest thing you’ve done that people will believe only when you show them some proof?
  6. Which social media app would you want to completely eliminate from this world and why?
  7. What are you phobic of?

  1. If you mistakenly drop your phone into a commode, would you use that phone again?
  2. What has been your most embarrassing moment in life so far?
  3. In an interview, if you are given a topic which you’ve never heard of and asked to speak a few lines about it, what would you do?
  4. If your car breaks down in the middle of a forest at night with no human in sight, what would you do?
  5. While traveling back home from work, if you happen to hear any news of terrorist attacks happening at many places around the city, will you panic or stay calm?
  6. Have you ever lied in your life? To whom and why?
  7. If you are thrown into a tiger’s cage, how will you save yourself?
  1. Can you walk amongst zombies or do you prefer lying down beside a mummy?
  2. Can you stay silent without talking a word for one full week?
  3. What is the weirdest thing that you have heard about yourself?
  4. Sing any song of your choice by mimicking Mickey Mouse’s voice.
  5. If your doctor informs you that you are suffering from a terminal illness, what would you do?
  6. If you are given a dare of pulling a prank on your professor/boss, will you do it?
  7. If everyone around you could turn into statues for an entire day, what would you do?

21 Questions To Ask Your Crush

If you want to play this game with your crush or someone you have taken a liking to, check out the questions below. You can even pose these questions to someone you are meeting up with for the first time to have a better understanding.

  1. Which color would you like to dress up in on your first date?
  2. Have you ever been seriously involved in any relationship but it didn't work?
  3. After a breakup, do you have the guts to get into a new relationship again?
  4. During your wedding, would you like to design your own vows?
  5. Do you enjoy being single or are you looking to enter into a serious relationship?
  6. What was your first impression of me?
  7. If you ever happen to cross paths with your ex, what would be your reaction?
  8. What is that quality which you don’t want your partner to have?
  9. Have you ever experienced true love?
  10. While texting your special one, do you use more emojis or keep it only as plain text?
  1. Have you ever done anything crazy to attract someone’s attention?
  2. Do you enjoy your dates or find them stressful?
  3. Do you take an effort and go out of your way to present yourself on a date or do you take it like any other casual outing?
  4. What kind of movies do you love watching?
  5. Are you more of a social media person or do you wish to keep all your special moments under wraps?
  6. Have you ever taken any inspiration from any couple?
  7. Would you take the initiative of patching up with your partner after a fight?
  8. Do you have any irrational fear in a relationship?
  9. Do you have any specific learning from your past relationships?
  10. What do you see as a red flag in a relationship?
  11. What would be your perfect question to ask me?

Read more: 5 Fun and Innovative Teamwork Games Your Employees Will Love

Good 21 Questions to Ask

If you want to engage with your friends in some terrific conversations, then check out these questions below. 

  1. Which dream of yours would you like to turn into reality?
  2. If given a choice between traveling to hell or no man’s land, which one would you choose?
  3. Which cartoon character can you relate to?
  4. If you happen to realize that your survival is just for 6 more months, what would you do?
  5. What is the topmost item on your bucket list?
  6. Would you wish to lead a celebrity life and experience all the luxuries or remain a common man and experience these as they come?
  1. You need to conduct a VIP interview and your choices are Barack Obama, Bill Gates, Steve Jobs, and Warren Buffet. Who will be your choice and why?
  2. Will you continue climbing atop the corporate ladder by crushing your dream passion or follow your passion instead?
  3. Which one would you choose here - staying satisfied with a low income or making lots of money and being very famous but having no family time?
  4. Would you like to do bungee jumping from a helicopter or jump using a parachute?
  5. If you had the power to become invisible for an entire day, what would you do?
  6. What is the first thing you like to do when you get up in the mornings?
  7. Who has inspired you the most in your life?
  8. Would you prefer watching your favorite shows on Netflix or love to watch your favorite childhood cartoon on TV?
  1. Which childhood memory would you wish to cherish forever?
  2. If you happen to win the show “Who wants to be a millionaire?”, what would you do with the prize money?
  3. If you would want to ask a very funny question to the next player, what would be your question?
  4. Which superpower would you love to have?      
  5. If you had to give up your favorite desire in exchange for traveling to your dream destination, would you do it?
  6. If you had the power to change time, would you like to visit your past or travel into the future?
  7. If you would become the next President of America even for a day, what is the most important thing you would like to do?

Some questions are a little serious and deep here and it would relieve you from any stress once you talk it out. If the above questions are answered with wise thoughts, we bet you will enjoy this entire question-answer session.

Read more: 8 Fun Online Zoom Games to Play with your Coworkers

good questions to ask image


The 21 Questions game can be really fun and engaging. If both the questions and the answers are intense then everyone’s enthusiasm and spirits will be high till the end. We hope that these questions will help you in engaging in some meaningful conversations with your friends and family members.

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FAQs: 21 Questions Game

Here are some commonly asked questions about the 21 Questions Game.

What to ask in 21 questions game?

You can ask a mix of deep questions, interesting and humorous questions, and even relationship-based questions. If you want to maintain the intensity of the game till the end, then you should choose the right kind of questions. Your group may lose interest while playing in case the queries are not smart, witty, and funny enough.

What are some good 21 questions for couples?

Some good 21 Questions include:

  • Which dream of yours would you like to turn into reality?
  • If given a choice between traveling to hell or no man’s land, which one would you choose?
  • Which cartoon character can you relate to?
  • If you happen to realize that your survival is just for 6 more months, what would you do?
  • What is the topmost item on your bucket list?

How do you play 21 questions?

There are many ways of playing this game. You can ask a question to all the players one by one and proceed to the next. You may even choose to ask 21 questions at a stretch to a single member. For a more intensive and fun game, you can choose to do a rapid-fire kind of question-answer session.

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