21 Questions Game [The Best 588 Questions to Ask]

The 21 Questions Game is just what it sounds like—you ask someone a total of 21 questions to get to know them better. It’s like a conversation filled with questions, and you can play it with friends, family, or even someone you’ve just met. 

It’s a perfect game for when you’re getting to know someone, want to pass the time on a long drive or break the ice at a gathering where not everyone knows each other well. The key is that everyone has a chance to share and listen, creating a warm and friendly vibe.

How to Play 21 Questions?

Classic Two-Person Game:

Setup: This version is intimate and meant for two players. It could be two friends, a couple, or even two people on their first date.

  • Step 1: You can flip a coin, or maybe the person whose birthday is next gets to ask the first question.
  • Step 2: One person asks a question, and the other person answers it. Try to make it a good question that lets you learn something fun or interesting about the other person.
  • Step 3: After the first person has answered, it’s their turn to ask a question. Now, it’s the first person’s turn to answer.
  • Step 4: Keep trading questions back and forth until you’ve asked 21 questions each.

Classic Group Game:

Setup: Gather your group of friends. You could be at a party, a get-together, or just hanging out.

  • Step 1: Sit in a circle or just close together so everyone can hear each other.
  • Step 2: Pick someone to start as the answerer. You could go by age, draw straws, or just volunteer.
  • Step 3: The person to the right or left of the questioner answers first, then it goes around the group.
  • Step 4: After every question, a new person asks the next one, moving around the group in the same direction.
  • Step 5: Keep this up until you’ve gone through 21 questions.

21 Questions to Get to Know Someone Deeply

  1. What’s a simple pleasure that makes you smile?
  2. What book had a significant impact on your life?
  3. What song could you listen to on repeat?
  4. What’s one of your fondest childhood memories?
  5. Who has been the most influential person in your life?
  6. What’s something you’ve always wanted to try but haven’t yet?
  7. What’s the best piece of advice you’ve ever received?
  8. What habit are you most proud of breaking?
  9. What place do you feel most like yourself?
  10. What’s something that scares you about the future?
  11. If you could solve one world problem, what would it be?
  12. In moments of self-doubt, what do you tell yourself?
  13. What’s a goal you have for the next year that feels daunting?
  14. What’s been your biggest learning experience in life so far?
  15. If you could relive one moment in your life, which would it be?
  16. What aspect of your personality do you feel is often misunderstood?
  17. What would you do with your life if you knew you couldn’t fail?
  18. How do you think your closest friend would describe you?
  19. What’s something you’ve never explained to anyone but wish you could?
  20. What personal challenge have you overcome that you’re proud of?
  21. Looking back over your life, what’s a lesson you’ve learned that you would want to share with others?

21 Questions to Ask Your Crush

  1. What do you like to do to unwind after a busy week?
  2. What’s your idea of a perfect adventure?
  3. What are some small things that bring you joy?
  4. What’s your ‘go-to’ movie for a feel-good night in?
  5. What’s something quirky about you that others might not guess?
  6. If you had a theme song, what would it be?
  7. What’s a hobby you’d like to pick up if you had the time?
  8. What’s the most interesting thing you’ve read or seen this week?
  9. What’s your favorite way to spend a day outdoors?
  10. What’s a talent you have that would surprise me?
  11. What’s your most cherished memory from childhood?
  12. If you could travel anywhere right now, where would you go?
  13. What makes you laugh out loud every time you think about it?
  14. What’s something you’re looking forward to in the next few months?
  15. If you could learn any skill instantly, what would it be?
  16. What’s something you’re really passionate about?
  17. Do you believe in fate or coincidences? Why?
  18. What does your ideal weekend look like?
  19. If you were to write a book, what would it be about?
  20. What’s an achievement you’re incredibly proud of?
  21. What’s one thing you’re secretly very good at

21 Questions to Ask a Girl

  1. What’s your favorite childhood book or story?
  2. What’s your favorite place you’ve ever visited?
  3. What’s a skill or hobby you’ve always wanted to learn?
  4. Who do you look up to as a role model?
  5. What’s the best gift you’ve ever received?
  6. What kind of art or creativity speaks to you?
  7. Where’s your favorite place to relax and clear your mind?
  8. What are you most passionate about currently?
  9. If you could have dinner with any historical figure, who would it be?
  10. What’s a movie that had a significant impact on you?
  11. What’s a lesson from your past that has shaped your outlook on life?
  12. What’s your go-to song for a sing-along?
  13. Do you have a cause that you feel strongly about?
  14. What do you think is the most important life skill to master?
  15. What’s your most treasured family tradition?
  16. If you had a superpower for a day, what would it be and why?
  17. What are you most grateful for in your life right now?
  18. What’s an adventure you’d love to go on one day?
  19. What’s a fear you’ve overcome in recent years?
  20. What does your perfect day look like from morning to night?
  21. Who do you confide in when you’re facing challenges?

21 Questions to Ask a Guy

  1. What sports do you enjoy watching or playing?
  2. What’s your favorite way to spend a Saturday?
  3. What would you do if you had a free day with no obligations?
  4. What invention do you think has changed the world the most?
  5. What’s something on your bucket list that you’re eager to check off?
  6. How do you like to stay active?
  7. What’s one of your favorite family memories?
  8. What are three things on your ‘must-do’ list for this year?
  9. What’s something new you’ve learned recently?
  10. Who inspires you to be a better person?
  11. What are you most looking forward to in the future?
  12. What’s been your favorite age so far, and why?
  13. If you could witness any event of the past, present, or future, what would it be?
  14. What’s a challenge you faced that taught you a valuable lesson?
  15. What do you consider your biggest success up until now?
  16. What book, movie, or TV show has influenced you?
  17. What was your dream job as a child?
  18. What’s one hobby you’d like to pick up if you had more time and resources?
  19. What’s one thing you wish people understood about you?
  20. What’s the most spontaneous thing you’ve ever done?
  21. What values are important to you in relationships?

21 Questions to Ask During a Date

  1. What’s something that makes you smile every time you think about it?
  2. What’s a hobby you’ve always wanted to spend more time doing?
  3. What’s a place you’ve always wanted to explore?
  4. What are three things you value most in life?
  5. What’s the best meal you’ve ever had?
  6. What’s the most memorable vacation you’ve taken?
  7. If you could spend a day with one person, alive or dead, who would it be and why?
  8. What achievement are you most proud of?
  9. What’s your favorite way to relax after a long week?
  10. If you could switch lives with one person for a day, who would it be?
  11. What’s something you’re looking forward to in the near future?
  12. What’s your favorite tradition or holiday, and what makes it special to you?
  13. What’s a subject you wish you knew more about?
  14. What’s the kindest thing someone has ever done for you?
  15. What’s something you’ve done that was totally out of your comfort zone?
  16. How do you like to celebrate your birthday?
  17. What’s one thing that can always make you laugh?
  18. If you could instantly master any skill, what would it be?
  19. What’s an important lesson you’ve learned from past relationships?
  20. What’s a dream you’ve had that you still think about?
  21. How would you describe your perfect weekend?

21 Questions to Ask Your Girlfriend

  1. What’s something small that I do that makes you really happy?
  2. Can you share a dream you’ve always had but never told anyone?
  3. What’s your ideal way to spend a rainy day together?
  4. What’s a fear you’ve conquered, and how did you do it?
  5. If we could travel anywhere together right now, where would you want to go?
  6. What’s a lesson you’ve learned from a past relationship that you value?
  7. What’s something you’re proud of but don’t get to talk about much?
  8. If you could relive a day from your past, which one would it be and why?
  9. What’s a goal you have that you think I could help you achieve?
  10. What’s something you’ve always wanted to do with a partner but never got the chance to do?
  11. How do you think experiencing love has changed you as a person?
  12. What’s one piece of advice you’d give to your younger self?
  13. What is something you’ve always wanted to say but haven’t found the right moment?
  14. If you could wake up tomorrow with a new talent or skill, what would you choose?
  15. What’s a movie that you can watch over and over again and still love?
  16. What’s an important value you think is crucial in our relationship?
  17. What’s one fear you would like to conquer together with me?
  18. What do you feel most passionate about in your life right now?
  19. If we made a time capsule to be opened in 10 years, what would you put in it?
  20. What’s something you feel is often misunderstood about you?
  21. How do you envision our future together?

21 Questions to Ask Your Boyfriend

  1. What little things can I do that would make you feel more loved?
  2. Can you tell me about a hobby or interest you’ve never pursued but always wanted to?
  3. If we could go on any adventure together, what would it look like?
  4. What’s been one of the most defining moments in your life so far?
  5. What traditions do you want to form in our relationship?
  6. What was the best part of your day today?
  7. Is there a memory from your childhood you find yourself returning to often?
  8. What’s one change you’ve made in your life that you’re particularly proud of?
  9. What experiences in your life have made you who you are today?
  10. What’s the most valuable lesson you’ve learned in a relationship?
  11. What’s a silly fear you have that you’d like to overcome?
  12. What goals do you have for the next five years?
  13. What’s a book that has significantly influenced your thoughts?
  14. If you had a day completely to yourself, what would you do?
  15. How do you think we can make our relationship even stronger?
  16. In what ways do you feel we’re similar, and in what ways do we differ?
  17. What’s a question you’ve never asked me but have always wanted to?
  18. If we were to make a bucket list together, what’s the first thing you’d add?
  19. What’s one thing in your life you’re looking forward to right now?
  20. If you found out today was your last day on Earth, what would you regret not doing?
  21. What’s the biggest dream you have for your future?

21 Questions for New Couples

  1. What initially attracted you to me?
  2. Can you describe your perfect day, from morning to night?
  3. What’s one thing from your bucket list that you’d like us to do together?
  4. How do you typically like to communicate your affection?
  5. Is there a book or movie that has profoundly affected you?
  6. What personal achievement are you most proud of?
  7. What’s one of the best compliments you’ve ever received?
  8. What’s an important life lesson you’ve learned that you’d want to share?
  9. What are some of your non-negotiables in a relationship?
  10. How do you prefer to handle disagreements or conflicts?
  11. What’s a hobby or interest you’re excited to share with me?
  12. What does your ideal work-life balance look like?
  13. What traditions or rituals do you hold dear and would like to continue?
  14. How do you rejuvenate when you’ve had a stressful time?
  15. What’s something that always brings a smile to your face?
  16. What goals are you currently working towards?
  17. What’s one of your favorite childhood memories?
  18. What’s a skill or talent you wish you had?
  19. What’s a challenge you’ve faced that has shaped who you are today?
  20. What’s your philosophy on personal growth and self-improvement?
  21. How do you envision the perfect relationship?

21 Questions for Long-Term Couples

  1. What’s something small I do that has made a big difference in your life?
  2. How have our shared experiences shaped our life together?
  3. What aspect of our relationship do you think we’ve done really well in?
  4. In what ways have you and I changed the most since we first met?
  5. What dreams or aspirations can we pursue in the next phase of our life?
  6. What new hobby or activity would you like to try together?
  7. If you could choose an aspect of our early days to bring back, what would it be?
  8. How can we spice up our regular routine in a way that excites both of us?
  9. What challenges in our relationship are you grateful for?
  10. What’s a recent moment between us that you felt really connected?
  11. How do you think our experiences have strengthened our love over time?
  12. What is something you’d like us to do more that we haven’t had time for lately?
  13. How do you see us evolving or growing in the coming years?
  14. What’s an area in our relationship you’d like us to focus on improving?
  15. What’s one of the most important things you’ve learned about yourself through our relationship?
  16. What adventure can we plan that’s unlike anything we’ve done before?
  17. If we could go back to any particular year of our relationship, which one would you choose and why?
  18. What’s one fond memory that you look back on and laugh about?
  19. Can you think of a time when you felt exceptionally proud of us?
  20. How can we make sure we’re not taking each other for granted?
  21. What’s something fun and out-of-the-ordinary that we could plan for our next anniversary?

21 Questions for Long-Distance Couples

  1. What was the best part of your day today, and how can I make it better from afar?
  2. If you could teleport to any place right now, where would we meet?
  3. What new thing have you discovered about yourself while we’ve been apart?
  4. How can we make our virtual dates even more fun and interesting?
  5. What’s something you’d like to learn or improve upon while we’re apart?
  6. Can you describe a perfect day we can plan for when we’re next together?
  7. Are there any songs that remind you of me? Which ones and why?
  8. If we were writing a story about our relationship, what would this chapter be called?
  9. What are some ways we can stay connected even when we’re busy?
  10. Is there an experience you wish we could have shared together recently?
  11. What’s a goal we can achieve together even while we’re long-distance?
  12. How do you deal with moments of missing me?
  13. What has long-distance taught you about our relationship?
  14. When you think about me, what’s the first memory that comes to mind?
  15. What do you anticipate most about living in the same place?
  16. In what ways has our distance made us stronger as a couple?
  17. What’s a movie or TV show you’ve been waiting to watch until we can watch it together?
  18. How can I make you feel loved and valued from a distance?
  19. What’s one promise we should make to each other?
  20. Have you found any hobbies or activities that help you feel closer to me?
  21. What surprises should we plan for each other?

21 Questions for Married Couples

  1. What’s something about our wedding day that you think about often?
  2. What’s one thing we’ve accomplished together that you’re really proud of?
  3. Is there something you would like us to do more often?
  4. What have you learned from our marriage that surprised you?
  5. What’s your favorite thing about our relationship?
  6. How do you think we’ve grown or changed as a couple?
  7. What’s one way I have been able to support you that you truly appreciated?
  8. If we could revisit one moment from our past, which would it be?
  9. What’s a new tradition you would like us to start?
  10. What’s been your biggest personal change since we got married?
  11. What do you think has been our greatest challenge, and how have we overcome it?
  12. How have your dreams and goals shifted since we’ve been married?
  13. What’s something you’ve always wanted to tell me but haven’t found the right time?
  14. How do you envision our retirement?
  15. What’s one thing about our daily routines that you value the most?
  16. If we could design our dream home together, what’s one feature it would definitely have?
  17. In what ways do you feel most loved by me?
  18. Where do you see our relationship in the next ten years?
  19. What’s something we have yet to experience together that you’re truly looking forward to?
  20. How can we continue to support each other’s individual goals?
  21. What’s a memory that stands out as a turning point for us?

21 Questions to Ask Friends

  1. What’s a simple pleasure that you absolutely love?
  2. Who has influenced you the most in life?
  3. What’s one thing that never fails to make you laugh?
  4. If you could learn any new skill in an instant, what would it be?
  5. What’s the most daring thing you’ve ever done?
  6. What’s an underrated movie or book that you think everyone should know about?
  7. What does your perfect weekend look like?
  8. What’s an important life lesson you’ve learned the hard way?
  9. What’s your guilty pleasure when it comes to TV shows or movies?
  10. If you could live anywhere for a year, where would it be?
  11. How has your life been different than what you’d imagined?
  12. What’s the best piece of advice you’ve ever been given?
  13. If you had the chance, what name would you give yourself other than your current one?
  14. What’s something you’re really proud of and why?
  15. How do you handle stress or pressure?
  16. What’s one thing you’re looking forward to in the next year?
  17. What’s one misconception people often have about you?
  18. What’s a hobby you’ve picked up during the last year?
  19. If you could change one moment in your life, which moment would it be and why?
  20. What has been your favorite age so far, and what made it special?
  21. What’s the biggest risk you’ve taken that paid off?

21 Questions to Ask About Childhood

  1. What’s your happiest memory from when you were a child?
  2. What games did you love to play as a kid?
  3. Who was your childhood hero, and why?
  4. What did you want to be when you grew up, and has that changed?
  5. What’s a piece of advice from your childhood that has stuck with you?
  6. What cartoons or shows were you obsessed with as a child?
  7. What was your favorite subject in school and why?
  8. Can you remember a particularly funny or embarrassing moment from your childhood?
  9. Which childhood book left a lasting impression on you?
  10. Did you have any quirky habits or nicknames as a child?
  11. What taste or smell brings you back to your childhood?
  12. Was there a place you visited as a child that you have fond memories of?
  13. What were your favorite family traditions growing up?
  14. If you could relive one childhood event, what would it be?
  15. Who was your most influential teacher?
  16. What’s something you miss about being a kid?
  17. What childhood toy meant the most to you, and do you still have it?
  18. What were you most afraid of as a child?
  19. Which childhood accomplishment are you still proud of?
  20. What childhood movie or story taught you a lesson that you still think about?
  21. How do you think childhood experiences have shaped who you are today?

21 Questions to Ask About Adulting

  1. What was your “I’m officially an adult” moment?
  2. What’s the most adult purchase you’ve ever made, and how did you feel about it?
  3. How do you define being ‘responsible,’ and do you feel you’ve achieved it?
  4. What’s the hardest lesson about adulting that you’ve learned?
  5. If you could give your younger self adulting advice, what would it be?
  6. What aspect of adulting were you totally unprepared for?
  7. What’s one responsibility you wish you could outsource forever?
  8. How do you balance your work life with personal time?
  9. What’s an essential skill you think every adult should have?
  10. What’s the best part about being an adult for you?
  11. What’s your go-to meal to cook when you want to feel more grown-up?
  12. How did you learn to manage your finances, and what tips would you share?
  13. What’s a common adulting myth you’ve found to be untrue?
  14. What adulthood challenge are you currently tackling?
  15. How do you handle the pressure of societal expectations as an adult?
  16. When it comes to adult life, what’s something you’re actually really good at?
  17. What part of adulting do you feel isn’t talked about enough?
  18. What’s something about adulting that you’ve become surprisingly passionate about?
  19. At what moment did you first feel proud of your adulting skills?
  20. How has your understanding of friendships changed as you’ve matured?
  21. What’s an adulting wisdom that has been a game-changer for you?

21 Questions to Ask Your Family

  1. What’s a family story you love but haven’t heard in a while?
  2. How has our family changed throughout the years?
  3. What’s the most valuable lesson you’ve learned from our family history?
  4. What’s your earliest memory of our family?
  5. Is there a family tradition you would like to begin or revive?
  6. What was the most memorable family vacation or trip?
  7. How do you think our family is unique?
  8. What’s something you admire about our family?
  9. What’s a talent or trait you think runs in our family?
  10. Is there a recipe that you feel defines our family’s gatherings?
  11. What’s one thing you’re grateful to our parents for teaching us?
  12. How do you think growing up in our family has shaped your personality?
  13. What’s the best piece of advice you’ve received from a family member?
  14. Is there a keepsake or heirloom that’s special to you?
  15. What challenges has our family overcome that have made us stronger?
  16. How would you describe our family dynamic?
  17. What’s a quality or characteristic you appreciate in each family member?
  18. What’s your favorite family holiday memory?
  19. What hopes do you have for our family’s future?
  20. What’s one way in which you feel you’ve contributed to our family?
  21. How do you envision our family reunions in the years to come?

21 Reflective Questions

  1. What’s a habit you’ve developed this year that you’re proud of?
  2. Which personal qualities do you think are your strongest?
  3. What’s a fear you’ve faced head-on in your life?
  4. How do you practice self-care when you’re feeling down?
  5. What’s a piece of advice that changed your outlook on life?
  6. Is there something you’ve always wanted to do but haven’t? What’s been stopping you?
  7. How do you define success, and do you feel successful?
  8. What’s a mistake you’ve made that ultimately led to personal growth?
  9. What brings meaning to your life?
  10. Who do you go to when you need honest life advice?
  11. What experience from your past has left a lasting impression on you?
  12. What’s something you struggle with in terms of self-development?
  13. When did you last step out of your comfort zone, and what was it?
  14. What’s an accomplishment that has given you the most satisfaction?
  15. What’s something that you believe in deeply?
  16. How has your perspective on the world changed as you’ve gotten older?
  17. What are three personal goals you’re currently working towards?
  18. How do you recharge after a stressful period?
  19. What’s an old dream you still hope to fulfill?
  20. How do you handle change and uncertainty in your life?
  21. What’s the most important question you ask yourself?

21 Flirty Questions

  1. What’s a romantic fantasy you’ve always had?
  2. How would you describe your flirting style?
  3. What’s the best date you’ve ever been on?
  4. What kind of outfit do you find really attractive?
  5. What’s something about you that might surprise me?
  6. What’s one thing that always makes you feel confident?
  7. When do you feel most attractive, and why?
  8. What does chemistry mean to you?
  9. Is there a scene from a movie that you find really romantic?
  10. What are your thoughts on love at first sight?
  11. How do you know when you’re really into someone?
  12. What’s your idea of the perfect kiss?
  13. How do you usually let someone know you’re interested in them?
  14. What’s a compliment that you’ve received that you still think about?
  15. What’s a little thing someone can do that really makes you swoon?
  16. What’s the most romantic thing someone has ever done for you?
  17. How do you feel about public displays of affection?
  18. Do you have a special spot where you like to take someone you’re interested in?
  19. What’s something about relationships you wish you knew earlier?
  20. Would you rather have a night out on the town or a quiet night in?
  21. What’s your biggest turn-on in a potential partner?

21 Fun Questions

  1. If you could become any animal for a day, which one would you be and why?
  2. Would you rather have to sing everything you say or dance wherever you go?
  3. What’s the funniest thing you’ve seen recently online?
  4. What’s an absolutely useless talent you have?
  5. If you were a kitchen utensil, which one would you be?
  6. What’s the worst fashion trend you participated in?
  7. If you could have an unlimited supply of one thing for the rest of your life, what would it be?
  8. What would the title of your autobiography be?
  9. If you could instantly become an expert in something, what would it be?
  10. What’s the most ridiculous fact you know?
  11. If you had to eat only one food for the rest of your life, what would it be?
  12. What’s the silliest reason you’ve ever gotten into a friendship quarrel?
  13. What would you do if you were invisible for a day?
  14. If you could create a holiday, what would it celebrate?
  15. What’s the best prank you’ve ever played or had played on you?
  16. What’s something absolutely everyone looks weird doing?
  17. If animals could talk, which species would be the rudest?
  18. If you were to perform in a circus, what would you do?
  19. What’s the strangest dream you’ve ever had?
  20. What would your super-villain or superhero name be, and what powers would you have?
  21. If you could switch lives with a cartoon character for a week, who would it be?

21 Deep Questions

  1. What do you think the meaning of life is?
  2. How do you measure happiness in your life?
  3. What do you think happens after we die?
  4. Do you think there’s life on other planets?
  5. What does freedom mean to you?
  6. What’s the biggest contribution you want to make in your lifetime?
  7. How do you deal with the thought of impermanence and change?
  8. What do you find most fulfilling about human connection?
  9. What do you think is humanity’s greatest challenge right now?
  10. Is there such a thing as absolute truth, and how do we recognize it?
  11. What’s the role of love in human existence?
  12. If you could know the absolute truth to one question, what question would you ask?
  13. What’s something you believe that most people disagree with?
  14. What impact do you want to leave on the people around you?
  15. What is the nature of reality in your perspective?
  16. How do personal experiences shape our view of the world?
  17. In what ways do you think technology will change our future?
  18. What does a well-lived life look like to you?
  19. How do you define consciousness?
  20. Do you think human beings have free will?
  21. What’s the most profound experience you’ve had?

21 Questions to Ask Pet Lovers

  1. What was the name of your first pet, and what was special about them?
  2. If you could have any exotic animal as a pet, what would you choose?
  3. What’s the funniest or most mischievous thing your pet has ever done?
  4. How has having a pet changed your life or lifestyle?
  5. What’s your favorite pet-related memory?
  6. If your pet could talk, what’s the first question you would ask them?
  7. Do you prefer pets with loads of energy or more calm and cuddly ones?
  8. What’s one piece of advice you’d give to a first-time pet owner?
  9. What are your thoughts on adopting pets vs. buying from breeders?
  10. Have you ever volunteered at an animal shelter?
  11. What’s your favorite animal charity or cause?
  12. How do you think having a pet impacts mental health?
  13. What’s the best way to celebrate a pet’s birthday?
  14. If you could take your pet on vacation anywhere, where would you go?
  15. What’s the most unusual pet you’ve ever encountered?
  16. Have you done any unique training with your pets?
  17. What’s the most important thing to consider when choosing a pet?
  18. How did you find your current pet?
  19. What funny quirks does your pet have?
  20. Do you think your personality matches the type of animals you have?
  21. What’s one pet product you couldn’t live without?

21 Questions to Ask Travelers

  1. What destination tops your travel bucket list and why?
  2. What is your most memorable travel experience?
  3. How do you prepare for a trip to a place where you don’t speak the language?
  4. What’s one travel tip you swear by?
  5. Have you ever had a travel mishap that turned into a positive experience?
  6. What’s the most interesting food you’ve tried while traveling?
  7. What do you always bring back from your trips?
  8. Do you prefer solo travel or with others?
  9. How do you immerse yourself in the local culture when you travel?
  10. What’s your favorite way to travel: plane, train, car, or ship?
  11. What do you think traveling has taught you about yourself?
  12. What’s the strangest cultural experience you’ve had abroad?
  13. Have you ever lived in another country? Tell me about it.
  14. What’s the longest trip you’ve ever taken?
  15. How do you stay on budget when you travel?
  16. What’s a destination you’ve visited that you think is underrated?
  17. Have you ever felt homesick while traveling? How did you cope?
  18. What’s the best travel advice you’ve ever received?
  19. How do you choose your next travel destination?
  20. What’s one place you’ve traveled to that felt like home?
  21. What’s the most adventurous thing you’ve done while traveling?

21 Questions to Ask Foodies

  1. What’s your favorite dish to cook, and where did you learn to make it?
  2. Have you ever taken a cooking class? What did you learn?
  3. What’s the most unusual food you’ve ever tried?
  4. Is there a particular cuisine that you love the most?
  5. How do you explore new foods and restaurants?
  6. What’s one ingredient you can’t live without?
  7. Do you enjoy cooking for others, or do you prefer to be cooked for?
  8. What’s your favorite food-related memory?
  9. How do you feel about fusion cuisines?
  10. Do you have a favorite cooking show or food-based book?
  11. What’s the best meal you’ve ever had, and what made it special?
  12. Have you ever experienced a food festival? Share your thoughts.
  13. What’s one kitchen gadget that has changed your cooking game?
  14. What’s the last recipe you’ve tried that was a hit?
  15. Do you have a unique food combination that you love but others might find strange?
  16. How do you approach trying foods you’ve never had before?
  17. What’s your go-to comfort food?
  18. Have you ever attempted to recreate a dish from a restaurant? How did it go?
  19. What’s your opinion on the rise of plant-based diets?
  20. If you could eat with any chef, dead or alive, who would it be and why?
  21. What role does food play in your culture or family traditions?

21 Questions to Ask Music Lovers

  1. What’s the first album you ever bought with your own money?
  2. Can you recall a concert that was life-changing for you?
  3. What song do you have on repeat right now?
  4. Is there a genre of music you used to dislike but now appreciate?
  5. Who is your all-time favorite band or artist, and why?
  6. How has your taste in music evolved over the years?
  7. Do you play any instruments? If not, which would you love to learn?
  8. What’s one song that can instantly put you in a good mood?
  9. Have you ever met a musician in person? What was that like?
  10. What’s an underrated artist or band that you think more people should listen to?
  11. What’s one music era you wish you could have experienced live?
  12. How do you discover new music?
  13. What’s a popular song or artist that you just can’t get into?
  14. What role does music play in your everyday life?
  15. Do lyrics or melody hold more importance for you?
  16. Is there a movie soundtrack you absolutely love?
  17. What’s a pivotal music memory from your childhood?
  18. Have you ever traveled to attend a music festival or concert?
  19. What album could serve as the soundtrack to your life?
  20. If you could curate a music festival, which artists would headline?
  21. How do you feel about cover songs and remakes — any favorites or ones you dislike?

21 Questions to Ask Sports Enthusiasts

  1. What’s your earliest memory of playing or watching sports?
  2. Do you have a favorite sports team? What makes them special to you?
  3. Have you ever played a sport competitively?
  4. What’s the most exciting match or game you’ve ever watched?
  5. How do you celebrate when your team wins?
  6. What’s your favorite sport to play vs. watch?
  7. Do you collect any sports memorabilia?
  8. Which athlete do you admire the most and why?
  9. Have you ever been to a big sporting event, like the Super Bowl or the Olympics?
  10. What life lessons do you think sports teach us?
  11. What’s your favorite sports movie or documentary?
  12. How has being a sports fan impacted your life?
  13. What’s a sport you know nothing about but would like to learn?
  14. Have you ever experienced a heart-breaking sports moment?
  15. Do you prefer individual sports or team sports?
  16. What does being a fan mean to you?
  17. Is there a sport or fitness trend that you’re currently into?
  18. If you could spend a day with any sports figure, who would it be?
  19. What’s the most impressive athletic feat you’ve witnessed?
  20. Do you participate in any fantasy sports leagues?
  21. What historic sports moment do you wish you could have witnessed live?

21 Questions to Ask Nature Lovers

  1. What’s your favorite type of natural landscape?
  2. Have you ever been on a wilderness survival trip?
  3. What’s the most beautiful place you’ve ever visited?
  4. How do you practice environmental sustainability in your everyday life?
  5. What’s a nature documentary or series that you’d recommend?
  6. What’s the best outdoor adventure you’ve ever had?
  7. Do you have a garden or like to grow your own food?
  8. What’s one endangered species that you’re passionate about saving?
  9. Have you experienced a moment in nature that felt spiritual or profound?
  10. What outdoor activities do you enjoy the most?
  11. Is there a national park or nature reserve that you dream of visiting?
  12. How does spending time in nature affect your well-being?
  13. What’s a challenging hike or climb you’ve accomplished?
  14. What’s your opinion on the importance of national parks?
  15. Do you enjoy going camping? What are your must-haves?
  16. What’s a creature you find fascinating in the animal kingdom?
  17. Have you engaged in any environmental volunteer work or activism?
  18. What’s something everyone can do to protect our planet?
  19. How do you stay safe while exploring the wilderness?
  20. Is there a place in nature you’d love to experience each season, and why?
  21. What’s the most incredible natural phenomenon you’ve witnessed?

21 Questions to Ask Fashionistas

  1. How would you describe your personal style?
  2. What’s a fashion trend you love right now?
  3. Who is your fashion icon or style inspiration?
  4. What’s your favorite piece of clothing you own and why?
  5. How has your style changed over the years?
  6. What’s a fashion rule you think is made to be broken?
  7. Do you have a go-to outfit for when you need to feel your best?
  8. What does fashion mean to you, and how does it influence your daily life?
  9. Is there a fashion era you would love to experience?
  10. What’s one clothing item you could never see yourself wearing?
  11. Have you ever experimented with a radical change in your look?
  12. What’s your approach to sustainable fashion?
  13. How do you decide what to wear for special occasions?
  14. What’s the most you’ve ever spent on a single piece of clothing or accessory?
  15. What do you think will be the next big thing in fashion?
  16. How do you organize your wardrobe?
  17. If you could design your own fashion line, what would it be like?
  18. What’s a fashion faux pas that really bothers you?
  19. How do you shop for clothes – impulses or planned?
  20. Have you ever attended a fashion show or week, and what was the experience like?
  21. What’s the oldest item in your wardrobe that you still wear?

21 Questions to Ask Tech-Savvy

  1. What’s one piece of tech you can’t live without?
  2. How do you think technology will change our daily lives in the next ten years?
  3. What’s the last app you downloaded that you find really useful?
  4. Are there any emerging technologies you’re particularly excited about?
  5. How do you stay updated on tech news and trends?
  6. What’s a common tech myth that you find yourself debunking often?
  7. How do you feel about the use of AI in everyday life?
  8. What’s a tech gadget that you think is severely underrated?
  9. Do you have any concerns about tech and privacy?
  10. What’s the most interesting tech startup you’ve heard about recently?
  11. How would you explain your job to someone without a tech background?
  12. What’s the most significant tech failure or fiasco that you remember?
  13. Have you ever done any coding or programming?
  14. What do you think is the biggest challenge in the tech industry right now?
  15. How has a particular technology improved your life?
  16. What tech do you think is overhyped currently?
  17. How do you manage screen time and digital well-being?
  18. What’s a piece of outdated tech that you miss or have fond memories of?
  19. What’s your take on virtual reality and augmented reality?
  20. Are you involved in any tech communities or forums?
  21. How do you see the intersection of technology and art?

21 Questions to Ask History Buffs

  1. What historical period fascinates you the most?
  2. If you could meet any historical figure, who would it be and why?
  3. What’s a historical event you wish more people knew about?
  4. How do you think studying history helps us today?
  5. Have you ever visited a place that made you feel like you were stepping back in time?
  6. What’s your favorite history book or documentary?
  7. Is there an artifact or object from history that you’d love to see in person?
  8. What’s a historical mystery that intrigues you?
  9. How has your interest in history shaped your worldview?
  10. What’s the most interesting historical site you’ve ever visited?
  11. If you could experience life in another era, which would you choose and why?
  12. Do you have any family history that you’re particularly proud of or interested in?
  13. What’s your favorite historical drama or period piece film?
  14. Are there any historical skills or crafts you’d like to learn?
  15. What’s a piece of historical wisdom that you think applies to today?
  16. What would you consider the most pivotal moment in history?
  17. How do you think the study of history will change with modern technology?
  18. What’s an underrated figure in history who deserves more recognition?
  19. If you could preserve one historical landmark forever, which would it be?
  20. How do you think future generations will view our current period?
  21. What do you find most challenging about understanding history?

21 Questions to Ask Bookworms

  1. Which book had such an impact on you that you think everyone should read it?
  2. Do you prefer fiction or non-fiction? Why?
  3. What’s a character from a book you felt a deep connection with?
  4. How do you choose the next book you’re going to read?
  5. Have you ever been part of a book club? If so, how was the experience?
  6. What’s the most memorable library or bookstore you’ve visited?
  7. Is there a genre you used to dislike but have come to appreciate?
  8. Have you ever read a book that changed your mind about something significant?
  9. What’s one book you didn’t expect to enjoy but ended up loving?
  10. Do you prefer physical books, e-books, or audiobooks?
  11. What’s a book you’ve read more than once and why?
  12. Which writer, dead or alive, would you love to have a conversation with?
  13. What’s your favorite quote or passage from a book?
  14. Is there a book from your childhood that you still think about?
  15. How do you organize your bookshelf?
  16. What’s a book that made you cry?
  17. Have you ever written any fan fiction or been inspired to write by a book you read?
  18. What’s your favorite book turned movie, and did it live up to expectations?
  19. How do you deal with a reading slump?
  20. Do you have any reading rituals or habits?
  21. If you could create a fictional world to live in, what would it look like?

Final Thoughts

Playing the 21 Questions Game is simple, but the conversations it starts can be very special. It doesn’t matter if you’re with one person or many, this game can bring you closer together.

Remember, every question is a chance to share and listen. And who knows? By the end of the game, you might see each other in a whole new light.

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Clariza is a passionate writer and editor who firmly believes that words have great power. She has a degree in BS Psychology, which gives her an in-depth understanding of the complexities of human behavior. As a woman of science and art, she fused her love for both fields in crafting insightful articles on lifestyle, mental health, and social justice to inspire others and advocate for change. In her leisure time, you can find her sitting in the corner of her favorite coffee shop downtown, deeply immersed in her bubble of thoughts. Being an art enthusiast that she is, she finds bliss in exploring the rich world of fiction writing and diverse art forms.