Fun questions to ask

Fun Questions to Ask
By Subhash Das Updated

Whether you are with your colleagues or with a bunch of besties, you always need to know fun questions to ask a person. These are such questions that do not need any context or introduction. The questions should be crisp, fun, and interesting at the same time.

133 Really Fun questions to ask Anyone for a Striking Conversation

To solve your woes, we have compiled a bunch of awesome fun questions. The questions are filled with joy, entertainment, and fun. Well! Get ready to pick up your favorite questions from this crazy list of fun questions to ask anyone and everyone.

  1. What is the worst character you played in your school drama?
  2. Has anyone ever cut your hair in a ridiculous way?
  3. What is the funniest joke you always used to tell in your childhood?
  4. Which food makes you happy 24×7?
  5. Is there any book that you can read every day?
  6. What is the most interesting thing about your nature?
  7. Is there any mark on your body that you think is very funny?
  8. How often do you preach about almost everything to your siblings?
  9. Is there anything you want to tell your Principal in school if you meet in person?
  10. How different is an adult from adolescence?
  11. What is the similarity between you and your mother?
  12. Have you ever fought over silly reasons with your parents?
  13. Who is the cooler between your mom and dad?
  14. Skill, talent, and money – Which one would you choose among these 3?
  15. At which age, you want to get married?
  16. What is the weirdest thing you want to try on your wedding day/
  17. If you could fight with one fictional character, then who would be that person?
  18. Do you like it when someone pays on your behalf?
  19. What do you do when someone passes a bad remark about you?
  20. Which film spooks you the most?

[ Read: Trickiest Would You Rather Questions ]

  1. Who is the most mischievous among your group of friends?
  2. Is there any myth or mystery you want to solve?
  3. What are the 3 things you want to do before your death?
  4. How many ratings would you give your courage?
  5. How strongly do you react in dreadful situations?
  6. Have you ever peed inside a public pool?
  7. Who admires you the most?
  8. What is the best compliment you have ever been told?
  9. Have you done anything daring ever?
  10. What do you do in your spare time?
  11. Have you ever thought of dating a celebrity?
  12. Do you have any weird hobby?
  13. What is the perception of people about you?
  14. How do you feel so confident always?
  15. Fun loving or jolly – how would you describe your nature?
  16. Are you someone who is an introvert or an extrovert? Or, an ambivert?
  17. What are three things you always carry with you whenever you are on a trip?
  18. Who is your favorite author of all time?
  19. Which countries do you want to visit in your life?
  20. How do you approach a stranger?
  21. Which is your favorite food of all time?
  22. Are you health conscious or weight conscious?
  23. Do you love yourself?

Cute Fun Questions to Ask

  1. How do you tackle difficult situations?
  2. What is your favorite go-to eat food?
  3. Do you dream often?
  4. What’s your ambition?
  5. What do you want to achieve in near-future?
  6. How do you want your dream home to be?
  7. Have you ever scolded anyone?
  8. What’s your best memory along with your parents?
  9. How willing were you to grow up quickly?
  10. Which childhood thing do you miss the most?
  11. Have you ever baked ice cream or cake?
  12. Which is your favorite flavor?
  13. How much do you love your bestie?
  14. What’s the craziest thing you have ever done with your best buddy?
  15. Are you weirdo or smart?
  16. What are the three things that you enjoy in your life?
  17. One skill that you want to learn as soon as possible?
  18. Who loves you the most in life?
  19. What do you want to learn as soon as you can?
  20. What is the best punchline you have ever heard of?
  21. Who can totally change you?
  22. One movie that has changed your life?
  23. What is the most amusing thing in your life?
  24. Have you ever gifted yourself anything?
  25. How do you celebrate your birthday?
  26. What is your staple party dish?
  27. Which is your favorite soft drink brand?
  1. What’s your favorite online shopping portal?
  2. Online shopping or offline shopping?
  3. Do you love your complexion?
  4. Do you love wearing perfume?
  5. How difficult or easy it was for you to accept the person you are?
  6. Which is your favorite piece of jewelry?
  7. Which type of attire makes you the most good looking?
  8. What do you usually prefer for your dinner?
  9. One funny incident that happened at your school and you would never forget that.
  10. Which television series is your absolute favorite?
  11. Netflix or YouTube?
  12. Village, town, or urban area – what’s your most favorite place?
  13. Which is your favorite season of all time?
  14. Which cuisine is very close to your heart?
  15. Have you ever received an expensive gift?
  16. Do you remember your first crush?
  17. What was your favorite subject in school?
  18. Has anyone ever forced you to a job?
  19. What if you find yourself in the middle of an island with no communication system?
  20. So, what are your favorite makeup brands?
  21. What is the secret of your successful life?
  22. Do you love freedom?
  23. On days, when you don’t feel energetic, what do you do?
  24. What do you usually order when you are at a restaurant?
  25. What are your favorite breakfast items?
  26. Have you ever went for a long drive?
  27. Which is the most amazing car of all time according to you?
  28. What’s your best throwback photo that you really liked?
  29. Whom do you trust the most in your life?

[ Read: Funny Questions to Ask a Guy ]

Fun Questions to Ask Friends

  1. Are you aware of your ancient family members?
  2. Who is the most interesting member in your whole family?
  3. Have you ever dropped a class in college?
  4. How many scores do you deserve for your overall performance in school?
  5. For which reason, the teachers used to scold you the most?
  6. Which is your favorite gadget?
  7. What’s your nickname?
  8. How does your boyfriend call you?
  9. Which according to you is a ‘must watch’ movie of all time?
  10. Have you ever dated an animated character in your dream?
  11. Which is your recent favorite game?
  12. Who is the most admired celeb ever?
  13. How many followers do you have on Instagram?
  14. If you are asked to share your most favorite picture on social media, what would that be?
  15. Do you love freebies?
  16. Are you an adventurous person?
  17. Is there anything that you feel frightened to imagine?
  18. What do you find very enigmatic in your life?
  19. Are you fascinated with anything?
  20. Who is your love of life?
  21. Are you a morning jogger or a late night walker?
  22. Have you ever spent a whole night in a jungle?
  23. Which sports activity is your absolute favorite?
  24. Have you ever met any strange yet funny person?
  25. One incident that you felt was quite entertaining?
  26. What is the most interesting thing about the internet?
  27. Which page do you visit often?
  28. What’s your wildest memory?
  29. Is there any product that you never leave your house without?
  30. What is your perception of love and life?
  31. Do you have any significant other?
  32. Where did you first met with your bestie?
  33. Who is the best cook in your whole family?
  34. Which type of news do you find very amusing?

There are a number of fun questions to ask anyone. But, these 133 questions are unbeatable in every sense. These are fun, informative, and as well as entertaining to ask. Surely, the questions would give a bundle of joy to both the questioner and the answerer.


  • The questions are fun, so the tone of asking should be fun-filled too.
  • Well! Maintain a positivity throughout the conversation.
  • It is better to not end up asking questions about past life that can dishearten the answerer.