Best Fun Questions to Ask (Ranked List) for 2023

Looking for fun questions to ask someone? Questions can be a great way to get to know someone. Questions can be a type of game. Or be used as conversation starters. It's up to the person who is asking the question. And how they'd like to use the question to bring connection, chemistry, and fun into a conversation.

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The best list of fun questions to ask. Free PDF resource included.

For players or people who are desiring to play a game with these questions. Gather together in a small group. Have each friend get together in a circle. Ask each player in the game in the prompt. Listen to their answers. And then continue by having the person to the right answer next.

Conversation starters are questions that get asked to reveal an interesting answer. They're great to ask with your best friend, boyfriend, family member, or a new friend. To play, ask, and answer the questions below. The questions are designed to spark interesting conversations amongst friends. And assist in revealing interesting things about one another.

List of Fun Questions to Ask

These are guaranteed to bring fun to any party. Either a laugh. Or a giggle. Enjoy! The prompts are funny, fun, and make for a great evening.

  1. Would you rather have a baby come out of your butt or sleep on nails?
  2. Would you rather eat snails or eat slugs?
  3. Would you rather bark every day you woke up or moo like a cow?
  4. Would you rather go to the zoo naked or go to school naked?
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Fun Questions to Get to Know Someone

Getting to know someone new? Questions can be a great way to get to know each other. A question can lead to another question. Or spark a new conversation the two of you weren't expecting. Try asking at least three to five questions to get the conversation started.

  1. If you had to look like one type of animal, what would it be?
  2. If you could live anywhere in the world, where would it be?
  3. What's the craziest thing you've ever done in your bedroom?
  4. What is one thing that you absolutely need to do in the mornings?
  5. What TV show would you be in if you were an actor?
  6. What's one of the worst purchases you've ever made?
  7. If you could go back in time, what part of history would you change?
  8. Would you ever fart in front of your family?
  9. If you had a crush on one of your friends, what would your pick-up line be?
  10. What's the worst date you've ever been on?
  11. What's your favorite thing to do when you're alone?
  12. Do you want a yacht or do you want a lake house?
  13. If you won the lottery, would you still want to work?
  14. If you were stranded on a desert island, how would you ask for help?
  15. Tell a funny story about your childhood.
  16. How would you get a free drink at a bar?
  17. If you heard a bump in the middle of the night, what would you do?
  18. What's one funny thing you look for in a girl?
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Fun Questions to Ask Friends

List of funny questions to ask best friends. To ask, get together with your closest friends. Pick a few of the questions from the list below. Or print out the question list. And then ask each other the questions. Try to be honest with the responses. Being honest makes the game a lot more fun!

  1. What do you think it would feel like to be an elephant?
  2. What's something about yourself that you want to keep secret?
  3. What's the last thing you did in the bathroom?
  4. If you were on a scavenger hunt, how would you find all the treasures?
  5. How would you have "the talk" with your kids?
  6. What's the worst thing you've ever seen your parents do?
  7. What are two words that describe our friendship?
  8. Who would you like to meet and have dinner with?
  9. What types of people would you like to surround yourself with?
  10. If you could go back in time, what era would you go to?
  11. What's the best way to have fun during the weekends?
  12. Who is someone you wish never existed? It can be now or in history.
  13. What's the best gift to give someone during the holidays?
  14. When is the last time that you were in love? And what did it feel like?
  15. Pick one of the following. Having the ability to fly, have X-RAY vision, or teleport.
  16. What celebrity body would you rate as "perfect?"
  17. What's the craziest way you've ever injured yourself?
  18. If you had to change your name, what would you change it to?
  19. What did you successfully hide from your parents?
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Fun Questions to Ask a Guy

These funny questions are guaranteed to bring the fun! Ask these questions to your boyfriend. Or to a guy that you have a crush on. To ask a guy these questions, surprise him. Gentlemen are going to appreciate getting asked questions randomly. Guys aren't often asked about themselves. This can make them feel appreciated. And potentially loved.

  1. Would you eat soup made out of cereal?
  2. Would you eat food that was under your bed for a day?
  3. If you were in a movie, which movie would it be?
  4. If you had to choose between giving birth to a baby or losing an arm, which would you choose?
  5. What memory do you have in life that would you like to start over?
  6. If you were to put together a car, how would you do it?
  7. What's your least favorite quality in a girl?
  8. What's one really massive pet peeve you have?
  9. What do you think you're so much better at than you probably are?
  10. How do you know when you fall in love?
  11. If you were to try to make one person laugh, how would you do it?
  12. What's a good way to make money?
  13. What's something "deep" that you've learned about life recently?
  14. What would be the worst thing to happen on a first date?
  15. What's the funniest thing you've ever done with your guy friends?
  16. What's the most boring sport, in your opinion?
  17. When's your favorite season of the year?
  18. If you didn't have to make money, what would your dream job be?
  19. What's the funniest joke you've ever heard?
  20. If you had to be one fictional character, who would it be?
  21. Who is the only person to make you pee your pants laughing?
  22. If you could meet any celebrity in real life, who would it be?
  23. If you had a million dollars, what would you do with it?
  24. What would be the theme song to your funeral?
  25. What's your favorite dessert?
  26. What professional athlete do you most want to be like?
  27. In a zombie apocalypse, how would you survive a cold winter?

Fun Questions to Ask Couples

Spark engaging conversations amongst couples with these fun questions.

  1. How do you manage meaningful connections?
  2. What's the silliest thing you've done with a boyfriend/girlfriend?
  3. What was your favorite subject in school?
  4. What's your favorite holiday?
  5. If you had to say you had a spirit animal, what animal would it be?
  6. What was the last "great idea" that you had, but never told anyone?
  7. What was your favorite toy when growing up?
  8. What's your "perfect vacation" look like?
  9. Who was the worst teacher that you had in school?
  10. What's the last song that you absolutely hated hearing on the radio?
  11. Is "self-care" important in todays world or do we over emphasize it?
  12. Would you drink milk past its expiration date?

Free PDF

Free PDF: Get the full PDF of this resource right here.

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author: patrick algrim
About the author

Patrick Algrim is a Certified Professional Resume Writer (CPRW), NCDA Certified Career Counselor (CCC), and general career expert. Patrick has completed the NACE Coaching Certification Program (CCP). And has been published as a career expert on Forbes, Glassdoor, American Express, Reader's Digest, LiveCareer, Zety, Yahoo,, SparkHire,,, FairyGodBoss,, St. Edwards University, NC State University,, Thrive Global,, Work It Daily, Workology, Career Guide, MyPerfectResume, College Career Life, The HR Digest, WorkWise, Career Cast, Elite Staffing, Women in HR, All About Careers, Upstart HR, The Street, Monster, The Ladders, Introvert Whisperer, and many more. Find him on LinkedIn.

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