275 Fun Questions to Ask Your Parents

Are you curious about your parents’ past or just want to share some laughs? Asking them fun questions is a perfect way to break the ice, discover new stories, and enrich family bonds. 

Whether you’re on a road trip or just hanging out on the couch, these questions are a fun way to get to know your parents better. So why wait? Fire away and let the good times roll!

Childhood Memories

  1. What was the funniest thing you did as a kid that no one knows about?
  2. Can you remember a time you laughed so hard you couldn’t stop?
  3. What was your favorite game to play during recess?
  4. Did you have a secret hideout as a child? Where was it?
  5. What is the most trouble you ever got into as a kid?
  6. Who was your childhood hero, and why?
  7. What was your dream job when you were ten years old?
  8. Can you remember a childhood dream that made you wake up laughing?
  9. What was the best birthday party you ever had as a kid?
  10. Did you have an imaginary friend? What was their name?
  11. What’s the funniest nickname you had growing up?
  12. What was your favorite cartoon or TV show?
  13. What was your biggest childhood fear?
  14. Did you ever try to run away from home? How far did you get?
  15. What’s the silliest reason you ever got grounded for?
  16. What was your favorite family vacation?
  17. Who was your most memorable teacher, and why?
  18. What’s the craziest fashion trend you followed?
  19. What was the name of your first pet, and how did you choose it?
  20. What was the most bizarre thing you believed as a child?
  21. Do you have a favorite book or story? What was it about?
  22. What was your go-to snack after school?
  23. Did you ever win an award or contest? What for?
  24. What childhood toy do you wish you still had?
  25. Can you recall a moment when you got lost? Where were you?
  26. What’s one thing you miss about being a kid?
  27. Which childhood friend do you wish you could see again?
  28. What was your least favorite chore?
  29. Did you ever make a time capsule? If so, what did you put in it?
  30. What did you do to pass the time on long car rides?
  31. Have you ever been to a summer camp? What was the best part?
  32. What’s the most adventurous thing you did as a child?
  33. Can you remember your first bicycle ride?
  34. What was your favorite subject in elementary school?
  35. Did you participate in any school plays or musicals? What role did you play?

Hypothetical Scenarios

  1. If you could have any superpower just for a day, what would it be?
  2. Would you rather travel to space or explore the depths of the ocean?
  3. If you could dine with any historical figure, who would it be and why?
  4. Imagine you won the lottery; what’s the first thing you’d buy?
  5. If you could live in any book, TV show, or movie, where would you choose?
  6. Would you rather be able to speak all languages or speak to animals?
  7. If you could bring back any fashion trend, what would it be?
  8. If you had to eat one food for the rest of your life, what would it be?
  9. What magical creature would you want as a pet?
  10. If you could instantly master any instrument, which would you choose?
  11. Would you rather have a time machine or a magic carpet?
  12. If you could live during any era in history, when would it be?
  13. Imagine you’re an inventor; what gadget would you create?
  14. Would you rather fight a horse-sized duck or a hundred duck-sized horses?
  15. If you could swap lives with anyone for a day, who would it be?
  16. Would you rather spend a day in Antarctica or the Sahara Desert?
  17. If you could witness any event in history, what would it be?
  18. What’s one thing you’d change about the world if you had the power?
  19. If you had to choose a theme song for your life, what would it be?
  20. Would you rather have the ability to fly or be invisible?
  21. If you could be a character in any video game, who would you be?
  22. What fictional world would you most like to live in?
  23. Would you rather be a pirate or a ninja?
  24. If you could turn any activity into an Olympic sport, what would you have a good chance of winning a medal for?
  25. Imagine you could open a shop; what would you sell?
  26. If you had to live in a TV show for a month, which would you choose?
  27. What’s one rule you would implement if you were in charge of the world for a day?
  28. If you could pick a new name based on your personality, what would it be?
  29. Would you rather live without music or without movies for the rest of your life?
  30. If you could have a dinner party with any five characters from literature, who would they be?
  31. Would you rather have teleportation powers or the ability to read minds?
  32. If you were an artist, what medium would you wish to master?
  33. If you could learn any skill instantly, what would it be?
  34. Would you rather explore a new planet or the deepest part of the ocean?
  35. If you could only keep three apps on your smartphone, which would you choose?

Favorites and Least Favorites

  1. What’s one food that you loved as a child but can’t stand now?
  2. What song always puts you in a good mood, no matter what?
  3. Who was your favorite band or musician as a teenager?
  4. What’s your all-time favorite movie that you can watch over and over?
  5. Is there a book you’ve read that completely changed your perspective?
  6. What’s your least favorite household chore and why?
  7. What’s your favorite holiday, and how do you celebrate it?
  8. What’s a pet peeve of yours that you wish everyone knew about?
  9. What’s one fashion trend you absolutely loved?
  10. What’s your go-to comfort food on a rough day?
  11. What’s a hobby you always wanted to pick up but never did?
  12. Do you have a favorite quote or saying that guides you?
  13. What’s the best piece of advice you’ve ever received?
  14. What was your least favorite job you’ve ever had?
  15. What’s your favorite family tradition that you’d love to pass on?
  16. What’s one city or country you’ve never been to but would love to visit?
  17. What’s your favorite sport to watch or play?
  18. What’s one movie that you think is overrated?
  19. Who’s your favorite fictional character?
  20. What’s your favorite season of the year, and why?
  21. What’s a skill or talent you wish you had?
  22. What’s your favorite thing to cook or bake?
  23. What’s one type of music you can’t seem to enjoy?
  24. What’s your favorite rainy-day activity?
  25. What’s your favorite thing about the city or town you live in?
  26. What’s a childhood movie that brings back the best memories?
  27. What’s the weirdest food you’ve ever tried and liked?
  28. What’s your least favorite exercise or workout?
  29. What’s something you’re surprisingly good at?
  30. What’s your favorite memory from our family vacations?

Mischievous Tales

  1. What’s the most mischievous prank you pulled off as a kid?
  2. Did you ever sneak out of the house as a teenager? Where did you go?
  3. Have you ever played a prank on a teacher or boss that went too far?
  4. What’s the funniest misunderstanding you’ve ever been a part of?
  5. Did you ever blame a sibling for something you did? What was it?
  6. What’s the most creative lie you told to get out of trouble?
  7. Have you ever taken something from a store without paying? What was it?
  8. What was your most successful scheme to make money as a kid?
  9. Did you ever create a secret code with friends? What was it for?
  10. Have you ever gotten lost on purpose just for the adventure?
  11. What’s the most daring thing you did to impress your friends?
  12. Did you ever fake being sick to get out of school? What did you do instead?
  13. Have you ever pulled a prank call that went hilariously wrong?
  14. What’s the most outrageous outfit you wore to defy dress codes?
  15. Did you ever sneak into a movie or concert? How did it go?
  16. What’s the funniest accident that happened during a family gathering?
  17. Have you ever set up a booby trap that backfired? What happened?
  18. Have you ever sent a fake love letter to someone? How did they react?
  19. Have you ever secretly altered a family recipe? Was it better or worse?
  20. What’s the silliest bet you’ve ever made?
  21. Have you ever pretended to be someone else online? Who did you pretend to be?
  22. What was your go-to excuse for missing homework?
  23. Have you ever gotten stuck somewhere really odd? How did you get out?
  24. Did you ever have a secret hand signal with friends? What was it for?
  25. What’s the most creative way you’ve skipped school?
  26. Have you ever orchestrated a food fight? What sparked it?
  27. What’s the worst haircut you’ve ever given yourself or someone else?
  28. Have you ever been caught doing something silly on camera?
  29. What’s the most bizarre thing you’ve done out of boredom?
  30. Did you ever make up a ridiculous game that became popular among your friends?
  31. What’s the most elaborate excuse you’ve ever made up?
  32. Have you ever gotten revenge in a silly way? What did you do?
  33. What’s the most imaginative story you told to cover up a blunder?
  34. Did you ever convince someone of a completely false story? How long did they believe it?
  35. Have you ever been part of a flash mob or unexpected public performance? What was it like?

Dreams and Desires

  1. What was one dream job you had as a kid that you still think about?
  2. If you could master any skill overnight, what would it be?
  3. What’s one hobby you wish you had more time for?
  4. Is there a place you’ve always dreamed of visiting? Where is it?
  5. Did you ever have a dream that was so vivid you believed it was real?
  6. What’s something you’ve always wanted to learn but haven’t yet?
  7. What’s one thing you wish you had done when you were younger?
  8. Do you have a bucket list? What’s at the top of it?
  9. What’s one talent you wish you were born with?
  10. If you could adopt any animal as a pet, what would it be?
  11. What’s a movie or book ending you would rewrite? How would it end?
  12. What’s one invention you wish existed?
  13. Have you ever dreamed of writing a book? What would it be about?
  14. What’s one thing you’re determined to achieve in your lifetime?
  15. If you could commit to any charity, what cause would it be for?
  16. Do you have a dream retirement plan?
  17. What’s one piece of advice you’d give to your younger self?
  18. Do you have a dream project you wish to complete one day?
  19. If you could live anywhere on Earth, where would it be?
  20. If you could reconnect with an old friend, who would it be?
  21. Do you wish you could go back to school for something else?
  22. What’s a musical instrument you’ve always wanted to play?
  23. If you could erase one regret from your life, what would it be?
  24. What’s one thing you hope to see in your lifetime?
  25. If you could guarantee one achievement for your children, what would it be?

Funny Family History

  1. What’s the funniest misunderstanding that’s ever happened in our family?
  2. Do we have any ancestors who were famously silly or notorious?
  3. What’s the oddest tradition our family has?
  4. Can you tell me about a time when a family event went hilariously wrong?
  5. Is there a legendary funny story that gets passed down in our family?
  6. Who in our family is known for being the prankster?
  7. What’s the silliest reason our family has ever gotten together?
  8. Have you ever discovered something surprising or funny about our ancestors?
  9. What’s the most memorable family inside joke?
  10. Did our family ever have a pet known for doing something hilarious?
  11. Can you share an embarrassing moment from a family gathering?
  12. What is the funniest gift you’ve ever received from a family member?
  13. Has our family ever started a weird but fun holiday tradition?
  14. What’s the most bizarre meal served at a family event?
  15. Did our family ever have a major mix-up with hilarious consequences?
  16. Who is the most eccentric relative we have, and why?
  17. What’s a funny habit or quirk one of our relatives is known for?
  18. Can you recount a time when a family photo or video shoot went comically awry?
  19. Has there ever been a “you had to be there” family moment?
  20. What’s the craziest thing a family member has done for love?
  21. Was there ever a family trip that turned into a comedy of errors?
  22. Do we have a relative who’s known for telling the tallest tales?
  23. What’s the most absurd thing passed down in our family?
  24. Can you share a story about a family member accidentally becoming a local legend?
  25. Has our family ever thrown a party that got out of control in a funny way?
  26. What’s a silly misunderstanding that led to a new family tradition?
  27. Did a family member ever make a comical mistake with technology?
  28. What’s the weirdest object that holds sentimental value in our family?
  29. Has a family member ever been mistaken for someone famous in a funny situation?
  30. What’s the funniest reason a family member has been late to an event?
  31. Can you tell me about a time when a family DIY project went hilariously wrong?
  32. What’s a funny story involving a family heirloom?
  33. Do we have a relative known for their unusual inventions or concoctions?
  34. Has a family member ever gotten into a silly situation while traveling?
  35. What’s the funniest thing a family member has done to try to save money?

Lighthearted This or That

  1. Would you rather always be 10 minutes late or always 20 minutes early?
  2. Pizza or burgers: Which is the ultimate comfort food?
  3. Beach vacation or mountain retreat?
  4. Dogs or cats: Who rules the pet world?
  5. Would you prefer to only watch movies or TV shows for the rest of your life?
  6. Summer or winter: Which season wins?
  7. Cake or pie: What’s the superior dessert?
  8. Super strength or super speed: Which power would you choose?
  9. Would you rather never have to sleep or never have to eat?
  10. Coffee or tea: Which is the better morning ritual?
  11. Would you rather read minds or accurately predict the future?
  12. Handwritten letter or email: What’s more meaningful?
  13. Would you rather explore space or the deep sea?
  14. Board games or video games: Which makes for a better game night?
  15. Classical art or modern art: Which do you appreciate more?
  16. Would you prefer a sprawling mansion or a cozy cottage?
  17. City life or country life: Where does your heart belong?
  18. Would you rather have an endless summer or an eternal winter?
  19. Stand-up comedy or a musical concert: Which is your ideal night out?
  20. Would you rather always have to say everything on your mind or never be able to speak again?
  21. Sunrise or sunset: Which do you find more beautiful?
  22. Intelligence or humor: What’s more important in a person?
  23. Scary movie or comedy film: What’s your pick for movie night?
  24. Would you rather win the lottery or live twice as long?
  25. Are you more into painting or photography?
  26. Fame or fortune: If you had to choose, which would it be?
  27. Going out for dinner or having a home-cooked meal?
  28. Would you rather live under the sea or on the moon?
  29. Live without music or live without books: What’s your choice?
  30. Teleportation or time travel: Which would you rather have the power to do?

Time Travel Delights

  1. Which decade of the past would you visit first in a time machine?
  2. Would you travel to the future to know what it holds for you?
  3. If you could bring back one fad or trend from the past, what would it be?
  4. What piece of advice would you give to your younger self if you could go back in time?
  5. Is there a mystery from the past you’d like to solve by traveling back in time?
  6. Would you rather see how the world is 100 years from now or how it was 100 years ago?
  7. If given the chance, would you change anything about your past?
  8. If you could attend any concert or event from the past, which one would it be?
  9. If you could bring one person from the past to the present, who would it be?
  10. Which extinct animal would you like to see if you could travel back in time?
  11. Would you go back in time to experience a day in the life of a royal?
  12. What future invention would you like to come back with to the present?
  13. Would you rather visit your future grandchildren or your ancestors?
  14. If you could relive the best day of your life so far, would you make any changes?
  15. Would you like to see how your hometown looked 100 years ago?

Who’s Most Likely to Questions

  1. Who’s most likely to forget an anniversary or birthday?
  2. Who’s most likely to spontaneously book a trip abroad?
  3. Who’s most likely to win a reality TV show?
  4. Who’s most likely to become famous for something silly?
  5. Who’s most likely to adopt a pet on a whim?
  6. Who’s most likely to invent something useful?
  7. Who’s most likely to laugh at the wrong moment?
  8. Who’s most likely to cry at a happy ending in a movie?
  9. Who’s most likely to become a social media influencer?
  10. Who’s most likely to spend all their money on something foolish?
  11. Who’s most likely to accidentally get locked out of the house?
  12. Who’s most likely to learn a new language first?
  13. Who’s most likely to take up a strange new hobby?
  14. Who’s most likely to sleep through an alarm?
  15. Who’s most likely to become a world traveler?
  16. Who’s most likely to start their own business?
  17. Who’s most likely to write a bestselling book?
  18. Who’s most likely to move to a different country?
  19. Who’s most likely to become a chef?
  20. Who’s most likely to run into a celebrity and not recognize them?
  21. Who’s most likely to become a secret agent?
  22. Who’s most likely to win a dance-off?
  23. Who’s most likely to give all their money to charity?
  24. Who’s most likely to survive on a deserted island?
  25. Who’s most likely to become the president of a fan club?
  26. Who’s most likely to get lost even with GPS?
  27. Who’s most likely to have the most pets?
  28. Who’s most likely to become a yoga instructor?
  29. Who’s most likely to binge-watch a TV series in one day?
  30. Who’s most likely to hold a world record?
  31. Who’s most likely to become an artist?
  32. Who’s most likely to be the first one on the dance floor?
  33. Who’s most likely to make friends with strangers?
  34. Who’s most likely to go viral on the internet?
  35. Who’s most likely to have the weirdest collection?

Frequently Asked Questions

What’s the most important thing to remember when asking these questions?

Keep the atmosphere light and fun. These questions are meant to entertain and bring you closer together. Respect boundaries, listen actively, and enjoy quality time with your parents.

Is there a “best time” to ask these questions?

While there’s no specific “best time,” choosing relaxed and comfortable settings with no rush or stress can create a more open and enjoyable environment for these conversations.

How can I make these conversation sessions more engaging and less repetitive over time?

Keep things fresh by mixing up the questions, incorporating new and seasonal topics, and even inviting your parents to come up with their own questions. This can turn it into an evolving family tradition everyone looks forward to.

Final Thoughts

These fun questions are your ticket to quality time and lots of laughs with your parents. You’ll learn things you never knew and get closer than ever. Go ahead, start asking, and enjoy the stories that come to life!

How useful was this post?

Click on a star to rate it!

As you found this post useful...

Share it on social media!

We are sorry that this post was not useful for you!

Let us improve this post!

Tell us how we can improve this post?

Photo of author

Robby is a multimedia editor at UpJourney with a journalism and communications background.

When she's not working, Robby transforms into an introverted art lover who indulges in her love for sports, learning new things, and sipping her favorite soda. She also enjoys unwinding with feel-good movies, books, and video games. She's also a proud pet parent to her beloved dog, Dustin.