340 Fun Questions For Any Situation

Invite some fun into your next conversation with the following funny questions. Whether you are chatting with your friends, want to spice up date night with your boyfriend or girlfriend, or want to make a great first impression on a first date, we have questions that are perfect for each occasion.

Sharing a laugh with the people around us helps us to feel closer and more connected to them, while also giving us the chance to get to know them on a more personal level. This list of questions is sure to put a smile on the face of whoever you’re talking to.


  1. To ask your friends
  2. To ask a girl you like
  3. To ask a guy you like
  4. To ask your girlfriend
  5. To ask your boyfriend
  6. To ask your spouse
  7. To ask your students
  8. Fun icebreaker questions for groups
  9. To ask your coworkers
  10. To ask your employees
  11. Fun ‘would you rather’ questions
  12. To get to know your teenager
  13. To get your kid talking
  14. To ask your family members
  15. To ask your best friend

Fun questions to ask your friends

You can get to know your friends and still have fun with them while doing so. The following questions are great to start a funny and light-hearted conversation. And you might even learn some surprising facts about your friends.

1. What is one thing you’re always waiting for an excuse to talk about?

2. If you were invisible the next 5 minutes, what would you do?

3. If you were a stripper, what would your stage name be?

4. Would you let me see your browser history?

5. What is the first CD you bought?

6. What word would you use to describe our friendship?

7. What book or series do you wish you could live in?

8. What is one thing your ex-boyfriend would warn me about you?

9. Have you ever pooped outside?

10. How would your parents describe your personality?

11. What sport do you think you would be the worst at?

12. What was your first email address?

13. What two items would weird out a cashier if you bought them together?

14. If 5-year old you was in your body, what’s the first thing you’d do?

15. What is the dumbest way you’ve broken a bone?

16. What is something that you are too old to do, but still enjoy doing?

17. What animal do you think I am the most similar to?

18. If you could elect anyone in the world as president, who would you choose?

19. Do you believe in aliens?

20. What was the best year of your life?

Fun questions to ask a girl you like

One of the easiest ways to create chemistry with a girl is by making her laugh. These funny questions are perfect to ask the girl you like. They might even help you make an impression great enough to land a date.

1. What is the funniest pick up line someone has ever tried on you?

2. Do you prefer a gym bod or a dad bod?

3. If you could have one superpower, what would it be?

4. What’s the worst relationship advice you’ve ever gotten?

5. Would you want the ability to read people’s minds?

6. What’s the weirdest text you’ve received recently?

7. What is the craziest thing that’s happened to you recently?

8. If your life had a mascot, what would the mascot be?

9. You know you’re amazing, right?

10. What is the best song to describe your life right now?

11. If you had to marry anyone today, who would you choose?

12. How do you stay so attractive?

13. If you could eat whatever you wanted without getting fat, what would you eat?

14. Would you rather be a guy or a girl?

15. Most awkward experience you’ve ever had with a crush?

16. If past lives existed, what do you think yours was?

17. Are you a hopeless romantic?

18. Do you like guys that ask a lot of questions?

19. Have you ever broken a bone? If yes, how?

20. What’s something silly that you take a lot of pride in?

Fun questions to ask a guy you like

Most of us appreciate someone who is able to make us laugh. When you first start dating someone, an easy and fun way to connect with your crush is by asking them funny questions. These questions to ask a guy you like can be used on your first or second date, and are also great to use over text if you’re still in the talking stage.

1. What’s the worst date you’ve ever been on?

2. What songs would you put on a mixtape for me?

3. What Disney princess would you be?

4. What’s your weirdest turn on?

5. How can you tell if a girl likes you?

6. What’s one word you would use to describe your best friend?

7. You’re about to get into a fight, what soundtrack comes on?

8. Have you ever had a crush on one of your teachers?

9. What’s your biggest kitchen mistake?

10. Have you ever been catfished on a dating app?

11. Do you have any hidden talents?

12. Can you guess what I’m thinking about right now?

13. Do you know any fun pick-up lines? Have you ever used them on someone?

14. What’s the most you’ve spent on something that you absolutely didn’t need?

15. If you had to listen to one song for the rest of your life what would it be?

16. What’s one thing you would never eat on a first date?

17. What’s the most embarrassing thing you’ve ever said or done on a first date?

18. What’s the best thing about being you?

19. What is one thing that you should probably do, but will probably never do?

20. What are the manliest and least manly things you’ve ever done?

Fun questions to ask your girlfriend

Date night with your girlfriend never has to get boring or repetitive, there is always more that you can find out about your significant other. These funny questions will help you to find out some random qualities about your partner that you may have never guessed.

1. Do you like hearing how beautiful you are?

2. What unnecessary products or services do you consider necessary?

3. If you had one week to live, what would you do?

4. Who is hotter: Hagrid, Dumbledore or Dobby?

5. What is the most romantic thing I’ve ever done for you?

6. What would you prefer, that people see you as smart or sexy?

7. When do you feel most yourself?

8. What three items would you bring to a desert island?

9. If you were a man for a day, what would you do?

10. How long would you survive a zombie apocalypse?

11. What would your dream bathroom look like?

12. What dunkin’ donut best describes you?

13. What song comes to your mind when you think about me?

14. What is the best true love story that you’ve heard?

15. Is there a moment that you knew you were in love with me?

16. Would you rather be fluent in every language or a master at every instrument?

17. What is the thing about our relationship that you love the most?

19. How do you like a man to show his feelings?

20. If you could have dinner with anyone in the world, who would you choose?

You might also be interested in this list with good questions to ask your girlfriend for any situation.

Fun questions to ask your boyfriend

Here is a list of some great questions to ask your boyfriend if you’re interested in finding out some of the more random qualities about him. There are even some questions about yourself that you can ask to find out how he really feels about you. The following questions will help you to deepen your relationship with your boyfriend while still having fun with him.

1. Is communication more important than sex in a relationship?

2. What is the strongest animal you could beat in a fight with no weapons?

3. If animals were to make wildlife documentaries about humans, what are some of the weird things they’d show?

4. What was one of your biggest ‘oh shit’ moments in your life?

5. What was your first impression of me?

6. Do you think it’s easier to ask for permission or forgiveness?

7. If you won the lottery what’s the first thing you would buy?

8. Would you ever spend the day at a nude beach?

9. Can you describe yourself in three words?

10. If you could have a child prodigy, what would you want their talent to be?

11. What outfit would you love to see me in?

12. Is there such a thing as being too in love?

13. What fictional character would you compare me to?

14. What should our couple name be?

15. What is your dream honeymoon?

16. What other hairstyles do you think I would look cute with?

17. If you could be incredibly skilled at one thing, what would you choose?

18. Would you rather be in love or be rich?

19. Who was the first person you kissed?

20. Where should we go on our next date?

Fun questions to ask your spouse

It doesn’t matter how much you think you know about your partner, there are always hidden gems that are waiting to be uncovered with the perfect funny question. Whether you want to bring a little extra fun into your everyday conversation or spice up your date night with your husband or wife, these are great questions to help you do so.

1. What’s one name you’d love to name our child but know I would never let you?

2. What do you like to do when I’m not around?

3. If you worked at a circus, what job would you want to have?

4. Would you rather live in a world of superheroes or magic?

5. If you had to describe me in 3 words, which would you choose?

6. How would you feel if you found out we were having twins?

7. If you could choose an age to stop aging at, what would it be? And why?

8. What is the funnest day we’ve ever spent together?

9. What is one thing I do for you that you never want me to stop doing?

10. What do you most look forward to about getting old?

11. What was a mistake that you made that actually turned out really well?

12. What’s on your bucket list?

13. If we could move anywhere in the world, where would you want to go?

14. What would your younger self not believe about your life today?

15. If you could be with anyone in the world, why would you choose to be with me?

16. What’s one thing that nobody knows about you?

17. What’s the best thing about being in a relationship with me?

18. Is there a silly accomplishment you have that you’re secretly proud of?

19. What’s the craziest thing you’ve ever dreamt about?

20. Have you ever changed your plans because of your horoscope?

Fun questions for students

Fun questions don’t have to be reserved just for adults. Asking these funny questions is a great way to break the ice and get to know your students better. The following questions are divided into three categories depending on the age group you work with, and the questions could be used as a great opener on the first day of school.

Elementary school

When it comes to kids in this age range, simple and fun are the best questions to ask. Have fun making your young students laugh with the following funny questions.

1. Would you rather have a pet dinosaur or dragon?

2. If you could be any flavor of ice cream what would you choose?

3. What cartoon character do you wish was real?

4. What do you want to be when you grow up?

5. What’s your favorite thing to do after school?

6. Would you rather be invisible or able to fly?

7. Would you rather have a dog or be a dog?

8. What’s your favorite book?

9. Who is your favorite superhero?

10. Do you have any brothers or sisters?

11. What’s the bravest thing you’ve ever done?

12. What’s the nicest thing you’ve ever done?

13. Do you like to sleep in on the weekends?

14. If we were to play hide and seek right now where would you hide?

15. If you could be any animal, what would you be and why?

16. If it was raining meatballs would you eat them?

17. What’s one food you love that most people hate?

18. Do you put cereal or milk in the bowl first?

19. Your teacher is a witch, and one day she gets tired of you not paying attention and zaps you into a book. What book would you hope she zaps you into?

20. What’s your favorite color?

Middle school

The following questions are great conversation topics that are funny and also open-ended enough to lead to deeper conversation. Create a classroom atmosphere that feels comfortable and fun for your students by asking fun questions meant just for middle school students.

1. What do you guys think I do for fun?

2. How old were you when you stopped believing in Santa?

3. Is a hot dog a sandwich?

4. If you had to be stranded on a desert island with someone from your class, who would you choose?

5. Who is the biggest role model in your life?

6. What is your favorite subject, and why?

7. What’s something you have in common with the person next to you?

8. If you were famous, what would you be famous for?

9. If you had a TV show about your life what would it be called?

10. If you could be any emoji what would you be?

11. If you started your own YouTube channel what would the videos be about?

12. What is a saying or expression that you probably use too much?

13. If humans started colonizing mars would you want to move there?

14. What do you think would be your perfect job?

15. What’s the silliest thing you’ve ever done because someone dared you to?

16. Would you rather live in an amusement park or a zoo?

17. If you could pick one subject to never have to learn again, what would you choose?

18. What’s your happiest memory?

19. If you could ban one food forever, what would you choose?

20. Would you rather be the size of an ant or the size of a giant?

High school

Connecting with students at this age can feel difficult. High school is when kids start making the transition from children to adults, and the in-between space can be uncomfortable. Using fun conversation starters is a great way to create space for you to get to know your students better.

1. If you had to audition for ‘America’s Got Talent” tomorrow, what would you do?

2. What has been your all-time favorite assignment?

3. Do you consider yourself an adult yet? Why or why not?

4. If you were in zero gravity, what’s the first thing you would do?

5. What is your favorite part about school?

6. Have you figured out what you want to be when you grow up yet?

7. Do you think that university is important?

8. Would you ever want to be an entrepreneur?

9. What’s a random talent that you have that your classmates don’t know about?

10. How do you feel about social media?

11. What’s the best life lesson you’ve learned so far?

12. If you could have any job after you graduate and know you’re going to be successful at it, what would you choose?

13. What is the most important quality you look for in a friend?

14. How well do you think you’d do in a zombie apocalypse?

15. What is the dumbest thing you’ve ever done with a friend?

16. What job do you think you are the most poorly suited for, and why?

17. What is something about yourself that you want me to know?

18. What is your biggest pet peeve?

19. Do you have your driver’s lessons yet?

20. Do you want to go to university to learn or just to have fun?

Fun icebreaker questions for groups

Showing up to meet a new group, whether it’s in a friendly or formal setting can be intimidating. Having some fun questions to ask the group is a great way to ease any sort of uncomfortable tension and get to know the people you are with.

1. If animals could talk, which one would you have beef with?

2. What kind of cult would you start?

3. Which Hogwarts house would you be in?

4. If you could be on any TV show, what would you choose?

5. What one skill would be really helpful?

6. What’s the funniest thing you wanted to be when you grew up?

7. If you were arrested, what would it be for?

8. What is one item you can’t live without?

9. What is the creepiest thing you could ask a stranger while walking down the street?

10. Have you ever built a snowman?

11. What’s something that’s really popular now, but in 5 years people will look back on and be embarrassed about?

12. Do you think it’s possible for men and women to just be friends?

13. What’s your guilty pleasure movie?

14. Is there anyone you would want to switch lives with?

15. If you had the chance to steal something, what would you take?

16. What’s the most overrated food?

17. Do you guys talk to your pets too, or just me?

18. If you could invent a holiday, what would it be?

19. For a day, would you rather be an elf or a hobbit?

20. What app on your phone do you waste the most time on?

Fun questions to ask coworkers

Ice breakers don’t always have to be incredibly awkward, and the best way to turn your coworkers into friends is with a little bit of humor. If you want ideas that will help you get to know your coworkers outside of usual work small-talk then the following fun questions are perfect for you.

1. Have you ever had a boss like Michael Scott?

2. Do you have any useless hobbies?

3. How would you politely end a conversation with someone who is annoying you?

4. What was your first job?

5. Who is one person you pretend to like but actually don’t?

6. If you won a million dollars would you continue working here?

7. What’s the best thing about getting older?

8. Is there anything that you wish you could unlearn?

9. What book do you think best describes you and your life?

10. What was the worst job you’ve ever had?

11. What is your favorite vacation destination?

12. What is your guilty pleasure?

13. Coffee or tea?

14. What’s your dream job?

15. What’s the weirdest thing you’ve ever eaten?

16. Who would you invite onto your talk show?

17. What’s your favorite dad joke?

18. Is there anything you pretend to hate but actually love?

19. Are you more of a cat person or a dog person?

20. How do you spend your time relaxing after work?

Fun questions to ask your employees

Laughing together is a great way to build rapport among a team of people. As a boss, asking funny questions is a great way for you to get to know your team members in a more relaxed way. Use the following questions to welcome a new employee, or at the start of team meetings to create a fun and welcoming work environment for your team.

1. Do you think you could ever be a famous ‘tik-tok’er?

2. If you could max out your credit card at any store and not have to pay the bill, which one would you choose?

3. Which one would you pick: being a supermodel, genius or super rich?

4. What do you think is the best quality in a boss?

5. What would be a good addition to our office?

6. How would you describe your job to a stranger?

7. If you had a talk show, who would you invite onto yours?

8. What is your favorite way to spend your weekend?

9. What is your guilty-pleasure app?

10. If you could retire tomorrow, how would you spend your time?

11. Would you rather be able to read people’s minds or be invisible?

12. What is a mistake you made early on in your career and what did you learn from it?

13. If you wrote a book tomorrow, what would it be about?

14. What do you do to relieve stress?

15. What energizes you at work?

16. Have you ever been fired from a job before? If yes, why?

17. Would you rather teleport or fly?

18. If you had an extra hour in the day, how would you spend your time?

19. If you could instantly master any skill, what would you choose?

20. How would your friends describe you?

Fun “would you rather”-questions

Simple games like ‘Would you rather’ may seem cheesy and outdated, but the truth is they’re a guilty pleasure for a lot of people, and a really fun way to get to know both old and new friends better. The following questions will have everyone in the room laughing during your next game night.

1. Would you rather hang out with me every day for the rest of your life or never see me again?

2. Would you rather fall in love tomorrow or win the lottery next year?

3. Would you rather be beautiful and dumb, or unattrative and intelligent?

4. Would you rather die before or after your partner?

5. Would you rather be in jail or in a coma for the next 5 years?

6. Would you rather be married to someone you love and be poor, or someone you don’t like and be rich?

7. Would you rather be able to shrink down to the size of an ant or grow to the size of a building?

8. Would you rather always be overdressed or underdressed?

9. Would you rather dine alone or take yourself out to the movies?

10. Would you rather lose your ability to see or hear?

11. Would you rather have a pause or rewind button in your life?

12. Would you rather give up food or water for the rest of your life?

13. Would you rather have more money or more time?

14. Would you rather have a time machine or a teleporter?

15. Would you rather lose the ability to lie or believe everything you hear?

16. Would you rather be the funniest or smartest person in a room?

17. Would you rather your mom or your dad picked your future spouse?

18. Would you rather find your soulmate or your purpose?

19. Would you rather be a wizard or a vampire?

20. Would you rather never have a best friend again or never get married?

Fun questions to get to know your teenager

Getting your teenager to say more than a few words to you can sometimes feel like an impossible task. The following questions are great conversation starters, and will allow you to have conversations with your teenager that are fun and light-hearted, and that have the potential to lead to more intimate and personal topics.

1. Would you ever want to be on a reality TV show?

2. If you won the lottery, how would you spend the money?

3. What is the most annoying personality trait someone can have?

4. What’s your favorite movie right now?

5. If you could go back in time what year would you travel to?

6. Who is your role model?

7. What are your goals for this year?

8. Do you want any tattoos or piercings?

9. As a parent, do I ever embarrass you?

10. What is your favorite thing to do as a family?

11. Do you consider yourself more of an introvert or extrovert?

12. What is something that you feel proud of yourself for?

13. What do you spend the most time thinking about?

14. What do you think makes a good friend?

15. If you were famous, what would you be famous for?

16. Do you ever want to get married and have kids?

17. What’s your favorite subject in school?

18. Do you have any celebrity crushes?

19. If you could travel anywhere, where would you want to go?

20. What’s your favorite family memory?

Fun questions to get your kid talking

So many children are easily excited and love to chat, but for the kids that are more on the shy side, finding a topic of conversation that is fun enough to break them out of their shell can feel tough. The following questions are creative, fun and easy to answer, so they’re great options when you’re trying to spark a conversation with your shy child.

1. What would you do if you could be invisible for the day?

2. If you could make a new animal, what would it be?

3. Do you have any imaginary friends? If yes, what’s their name?

4. If you could choose your own name for yourself what would you choose?

5. What do you want to be when you grow up?

6. What is your favorite animal, and why?

7. How do you feel about school?

8. Who is your favorite teacher?

9. What is the best dream you’ve ever had?

10. Who is your best friend, and why?

11. If you could meet any famous person, who would you choose?

12. What’s the nicest thing you’ve done for someone recently?

13. What is the funniest thing that’s ever happened to you?

14. If you could have any animal as a pet, what would you choose and why?

15. Do you think that your toys are like the toys from ‘toy’s story’ and come alive when you’re not there?

16. If you could only eat one food for the rest of your life, what would you choose?

17. Do you think mom or dad is a better cook?

18. What would be your perfect birthday party?

19. What’s your favorite song?

20. If you could talk to your pet, what do you think they would say?

Fun questions to ask your family members

As you grow up it’s always enjoyable taking a trip down memory lane, especially with the people who know you the best, your family. The following questions have been created specifically to ask the people closest to you. Make sure your next family gathering is full of laughter by asking the following funny questions.

1. Do you remember what I wanted to be when I grew up?

2. What do you think is my most annoying quality?

3. If you got a call about a family member being arrested, who would you assume it is?

4. Who is the messiest?

5. What is the funnest day we spent together as a family?

6. What do you miss most about us being kids?

7. Are there any family traditions that we don’t do and you’d like to bring back?

8. What did you find the most rewarding about being a parent?

9. What did you find the most challenging about being a parent?

10. What was your favorite TV show growing up?

11. Who was the kid that got in the most trouble growing up?

12. Who’s the more lenient parent?

13. Is there anything that you swore you’d never do as a parent but ended up doing?

14. Who makes the most noise in the morning?

15. How did Grandma and Grandpa meet?

16. What do you think is the secret to a long and happy marriage?

17. Which family pet was your favorite and why?

18. Who in the family is the best cook?

19. What do you think our parents did the best job of teaching us?

20. Did you ever play pranks on anyone in the family?

Fun questions to ask your best friend

For a lot of us, our best friend is the person who knows us better than anyone else in the world. They’re the person that we laugh the hardest with, and that we feel we can be our most authentic self with. The following questions are definitely just for adults, and are probably a little too out there to ask just any of our friends which is why they’re perfect for your bestie.

1. If you died right now, what would you leave me in your will?

2. When was the last time you peed your pants?

3. If I could set you up on a blind date with any celebrity, who would you choose?

4. What is something surprising that I don’t know about you?

5. When was the last time you lurked your ex on social media?

6. Who was your least favorite boyfriend of mine?

7. What is one thing I do that is guaranteed to annoy you?

8. Who’s number 1 on your hit list?

9. If a genie could grant you three wishes, what would you choose?

10. Who would you get to play you in the movie of your life?

11. Would you ever want to have a sugar daddy or mommy?

12. What crime do you think I’d be arrested for?

13. What’s the last thing you ordered off Amazon?

14. On a scale from 1-10 how basic do you think I am?

15. What’s the most embarrassing thing your parents caught you doing when you were younger?

16. If you had to choose between always being naked or having your thoughts appear above your head in a thought bubble, what would you choose?

17. Have you ever taken a scandalous photo of yourself?

18. Do you sleep with a stuffed animal?

19. Who do you think is the hottest guy or girl in this room?

20. Have you ever had a crush on your friend’s boyfriend or girlfriend?

Viktor is a Counselor specialized in interpersonal communication and relationships. He manages Socialpro’s scientific review board. Follow on Twitter or read more.

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