390 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!

Fun Questions About Their Love Story

  1. How did you first meet each other?
  2. Who made the first move?
  3. What was your first date like?
  4. What was the first movie you watched together?
  5. When did you know you were in love?
  6. How did you introduce each other to your families?
  7. Was it love at first sight, or did it take time?
  8. What was the first gift you gave each other?
  9. How did you handle your first fight or disagreement?
  10. Where did you go for your first vacation together?
  11. Did you have a special song?
  12. What were your first impressions of each other?
  13. Who said “I love you” first?
  14. What was the most romantic thing you ever did for each other?
  15. How long did you date before moving in together or getting married?
  16. How did you propose or decide to get married?
  17. Where did you go for your honeymoon?
  18. What obstacles did you face as a couple, and how did you overcome them?
  19. How did your friends react to your relationship?
  20. Did you ever break up and get back together?
  21. What traditions did you start as a couple?
  22. What were your favorite activities to do together?
  23. What’s the most meaningful gift you ever received from each other?
  24. How did you celebrate anniversaries?
  25. What’s the biggest lesson you’ve learned from each other?
  26. How did you decide on names for your kids?
  27. How did you support each other during tough times?
  28. Who is the better cook?
  29. What’s the most adventurous thing you’ve done as a couple?
  30. What do you love most about each other now?
  31. Did you ever write love letters to each other?
  32. Who is the more organized one in the relationship?
  33. Did you ever take a road trip together? Where did you go?
  34. Was there ever a moment when you thought you might not end up together?
  35. What’s the smallest thing that made a big difference in your relationship?
  36. Who is the better dancer?
  37. How did you decide which city or place to live in together?
  38. What’s a funny story that you both remember but tell differently?
  39. Who is better at remembering important dates, like anniversaries?
  40. What was the first piece of furniture you bought together?
  41. How did you celebrate your first holiday as a couple?
  42. Who is more likely to deal with a spider in the house?
  43. What was the first major purchase you made together?
  44. Who takes longer to get ready in the morning?
  45. Did you have any favorite restaurants or go-to date spots?
  46. How did you navigate your first big life change together, like moving or changing jobs?
  47. Did you ever have a pet together before having kids?
  48. What was the first sporting event you went to as a couple?
  49. Who usually wins when you play games or sports together?
  50. What’s a silly or cute nickname you have for each other?
  51. What’s the most spontaneous thing you’ve ever done together?
  52. Who’s the better driver?
  53. What’s a movie or show you both enjoy watching again and again?
  54. Did you ever take cooking classes or learn something new together?
  55. Who’s the first one to apologize after an argument?
  56. Did you ever go camping or hiking together?
  57. What’s the most exotic or far-off place you’ve visited as a couple?
  58. How did you both feel when you found out you were going to be parents?
  59. Who came up with the best surprises for birthdays or anniversaries?
  60. Did you both support the same sports teams?
  61. Who’s more tech-savvy?
  62. Have you ever renewed your wedding vows?
  63. What’s your longest time apart, and how did you cope?
  64. Who’s more likely to plan date nights?
  65. What’s one talent or skill the other has that you admire?
  66. Who usually chooses the vacation spots?
  67. Was there ever a moment when one of you saved the day?
  68. What’s the craziest weather you’ve experienced together?
  69. Did you ever take part in a community event or volunteer together?
  70. What’s your go-to karaoke duet?

Fun Questions Abou Raising Kids

  1. What was the most surprising thing about becoming a parent for the first time?
  2. Did you read any parenting books? Which ones?
  3. What was your go-to method for getting us to fall asleep as babies?
  4. What’s the funniest thing one of us said as a kid?
  5. Did we have any strange eating habits?
  6. What was the most memorable school event or performance you attended for us?
  7. How did you pick our schools?
  8. What was the most challenging age for each of us to parent?
  9. What’s a toy or game you couldn’t stand, but we loved?
  10. How did you decide on punishments or time-outs?
  11. Did you ever catch us doing something cute or funny when we thought you weren’t looking?
  12. What was the most creative way you kept us entertained on long trips?
  13. Did you ever have to play referee between us and our friends?
  14. What were your tricks for getting us to eat our vegetables?
  15. What’s the most bizarre question one of us asked as a kid?
  16. How did you approach “the talk” about the birds and the bees?
  17. What’s a piece of technology you had a hard time getting used to for our sake?
  18. What’s the most memorable holiday season with us?
  19. Did we have any imaginary friends or funny fears?
  20. How did you decide who would stay home when we were sick?
  21. What’s the funniest or most awkward parent-teacher meeting you’ve been to?
  22. Did you have any secret codes or phrases only our family understood?
  23. What were the shows or movies we watched over and over again?
  24. How did you feel about our first day of school?
  25. What hobbies did you hope we would pick up?
  26. Did you ever hide from us to eat a treat or have a moment of peace?
  27. What’s something we did as kids that melted your heart?
  28. How did you feel when we learned how to drive?
  29. What’s a childhood milestone for each of us that you were proud of?
  30. What was your go-to lullaby or bedtime story for us?
  31. Did you have any unique or funny ways to celebrate our birthdays?
  32. How did you handle it when we started asking for pets?
  33. What’s a lesson you tried to teach us that backfired or turned funny?
  34. Did you ever embarrass us in front of our friends, even if you didn’t mean to?
  35. Were there any household chores you wish you’d taught us earlier?
  36. Did we ever say or do something that completely surprised you in a good way?
  37. What was your reaction the first time we cooked or baked something?
  38. Did you ever receive parenting advice that you found hilarious or bizarre?
  39. What’s something we misunderstood as kids that you found adorable?
  40. How did you feel when we brought home our first report cards?
  41. Were there any public places you dreaded taking us to?
  42. What was the most challenging part of helping with our homework?
  43. What’s the silliest way we tried to act older than we were?
  44. Did we ever give you a really funny or strange gift?
  45. What was the most amusing tantrum one of us threw?

Fun Questions About Memorable Vacations

  1. Do you have a favorite vacation spot you keep returning to?
  2. What’s the most adventurous vacation you’ve been on?
  3. Have you ever had a vacation go completely wrong? What happened?
  4. What’s the farthest place you’ve traveled to?
  5. Do you prefer beach vacations or exploring cities?
  6. What’s a place you visited that was totally different than you expected?
  7. Have you ever been on a cruise?
  8. What’s your dream vacation destination?
  9. What’s the most beautiful place you’ve ever visited?
  10. How do you usually plan your vacations?
  11. What’s the most interesting food you’ve tried on vacation?
  12. Have you ever had a truly relaxing “do-nothing” vacation?
  13. Have you ever visited a place where you didn’t speak the language?
  14. What’s the most educational trip you’ve taken?
  15. Do you collect any souvenirs from your trips?
  16. Have you ever traveled with another family or a group of friends?
  17. What’s the best hotel or accommodation you’ve stayed at?
  18. Have you ever gone camping or glamping?
  19. How do you keep busy on long flights or drives?
  20. Have you ever visited any famous landmarks or wonders of the world?
  21. What’s the most memorable event or festival you’ve attended on vacation?
  22. Do you like to take a lot of photos on your trips?
  23. Have you ever taken a spontaneous trip with no plan?
  24. What’s the most romantic vacation you’ve had?
  25. Do you have any funny or embarrassing vacation stories?
  26. What was your favorite family vacation with the kids?
  27. Have you ever visited a place just because you saw it in a movie or read about it?
  28. What’s the one place you’d love to visit again?

Fun Questions About Family

  1. Who was the funniest person in the family growing up?
  2. Do you have any family recipes that have been passed down?
  3. What’s a family tradition you loved as a kid?
  4. Who was the strictest person in the family?
  5. What’s the most important lesson your parents taught you?
  6. Are there any famous or well-known people in our family history?
  7. How did you come up with names for your kids?
  8. What’s a talent or trait that runs in the family?
  9. Were there any family businesses or special crafts?
  10. Did our family come from another country originally?
  11. Who is the oldest relative you remember meeting?
  12. Did you have any family friends you saw all the time?
  13. Are there any stories of great-grandparents or older ancestors?
  14. Did you have a favorite toy or item that got passed down in the family?
  15. What’s a funny story from a family wedding or big event?
  16. Do we have any family secrets or legends?
  17. Were there any family reunions or big get-togethers?
  18. What were the chores you had to do growing up?
  19. Who in the family are you most similar to?
  20. Did you have a family member who influenced your career or hobbies?
  21. What’s the best piece of advice a family member gave you?
  22. Did you share a room with your siblings?
  23. Were there any family games or activities you did on weekends?
  24. How did you celebrate birthdays when you were young?
  25. Were you close with your cousins?
  26. How did the family react when you decided to get married or have kids?
  27. Was there a family member known for telling tall tales or funny stories?
  28. Do we have any relatives who were involved in historical events?
  29. What’s a food that everyone in the family seemed to love?
  30. Who was the peacemaker in the family?
  31. Did anyone in the family serve in the military?
  32. Was there a family member who was especially good at a sport?
  33. What’s the most touching moment you remember from a family gathering?
  34. Did you have a family garden or special outdoor spot everyone loved?
  35. Were there any family members who lived in a different country?
  36. Did anyone in the family have a unique or odd job?
  37. What’s a piece of family history you wish was documented better?
  38. Who was the best storyteller in the family?
  39. What’s the best gift you ever received from a family member?
  40. Were there any family rivalries or feuds?
  41. Who was the most artistic or creative person in the family?

Fun Questions About Embarrassing Moments

  1. What’s an embarrassing fashion trend you followed?
  2. Did you ever get caught doing something you shouldn’t have?
  3. Have you ever had an embarrassing nickname?
  4. What’s the most embarrassing song you loved?
  5. Did you ever trip or fall in a public place?
  6. What’s an awkward job interview story?
  7. Have you ever had a funny cooking or baking mishap?
  8. What’s the silliest argument you ever got into?
  9. Have you ever forgotten someone’s name right after meeting them?
  10. Did you ever send a text or email to the wrong person?
  11. What’s an embarrassing moment from your school days?
  12. Have you ever been caught singing or dancing when you thought you were alone?
  13. Did you ever get lost in a really obvious or funny way?
  14. What’s an embarrassing thing you believed as a kid?
  15. Have you ever had a funny or embarrassing gym moment?
  16. What’s an embarrassing story from when you were dating?
  17. Have you ever had a “foot in mouth” moment?
  18. Did you ever have a wardrobe malfunction?
  19. Have you ever tried to impress someone, and it backfired?
  20. What’s an embarrassing moment you had with a boss or coworker?
  21. Did you ever misunderstand a saying or phrase?
  22. What’s the most embarrassing thing you’ve said in front of a crowd?
  23. Have you ever been pranked or pranked someone else?
  24. What’s an embarrassing hobby or interest you had?
  25. Have you ever been scared or jumped in a funny way?
  26. Did you ever embarrass yourself in front of your in-laws?
  27. What’s an embarrassing childhood habit?
  28. Have you ever had an awkward or funny encounter with a celebrity?
  29. Did you ever get stuck somewhere?
  30. What’s the most embarrassing TV show or movie you love?

Fun Questions About Their Childhood

  1. What was your favorite game to play outside?
  2. Did you have a favorite toy growing up?
  3. What’s the craziest thing you did with your friends?
  4. What was your favorite snack as a kid?
  5. Did you have a pet? What was its name?
  6. How did you meet your best friend?
  7. What was your favorite TV show or cartoon?
  8. Did you ever get into trouble? What happened?
  9. What did you want to be when you grew up?
  10. How did you spend your summer vacation?
  11. What was the best birthday gift you ever got?
  12. Did you ever run away from home, even just for a little while?
  13. What was the most popular song when you were a kid?
  14. How did you celebrate the holidays?
  15. Were you good at keeping secrets?
  16. Who was your hero or role model?
  17. Did you collect anything? Like stamps or cards?
  18. Did you have a clubhouse or a secret spot?
  19. Did you ever win a prize or an award? For what?
  20. What chores did you hate the most?
  21. Did you have a nickname? What was it?
  22. How did you get to school?
  23. What was your favorite book?
  24. Did you ever make something cool in art class?
  25. What was the first movie you saw in a theater?
  26. Did you go to any concerts when you were young?
  27. What was the first sport you played?
  28. Were you ever in a school play or show?
  29. What was your favorite subject in school?
  30. What was your least favorite food as a kid?
  31. What’s the most adventurous thing you did?
  32. Did you ever go camping or on a big family trip?
  33. What was the coolest place you visited as a kid?
  34. Did you have a treehouse or a fort?
  35. Who was your childhood celebrity crush?
  36. What was your favorite candy or sweet treat?
  37. Do you have a favorite comic book or magazine?
  38. What was the first album or record you ever bought?
  39. Did you have a favorite amusement park or a fun place to go?
  40. What was your favorite thing to do on the weekends?
  41. Did you ever go on a trip without your parents?
  42. Were there any local legends or ghost stories that you believed in?
  43. Did you ever have a summer job? What was it?
  44. What was the most important lesson you learned from your parents?
  45. Did you have a bike? 
  46. Where did you like to ride it?
  47. How did you spend your pocket money?
  48. What games did you play on family game nights?

Fun Questions About Their School Days

  1. Who was your favorite teacher, and why?
  2. Did you ever cheat on a test?
  3. What was your go-to lunch in the school cafeteria?
  4. Were you part of any clubs or teams?
  5. Did you ever get sent to the principal’s office? What for?
  6. What was the most challenging class you took?
  7. What was the first dance or social event you went to?
  8. Did you have a crush on anyone? Did they know?
  9. Were you ever late to class?
  10. What was the best field trip you ever went on?
  11. Did you have a favorite spot in the library?
  12. What was the most embarrassing moment you had in school?
  13. How did you make your first friend in school?
  14. Did you ever skip school?
  15. What was the coolest project you ever did?
  16. Did you play any musical instruments?
  17. Were you good at sports?
  18. Did you ever lose something important at school?
  19. What subject did you struggle with the most?
  20. Were you part of the school newspaper or yearbook?
  21. Did you ever have a substitute teacher that was really fun or really strict?
  22. What was your best memory of high school?
  23. Were you ever part of a talent show?
  24. Did you ever have homework you just couldn’t do?
  25. How did you pick your classes each year?
  26. Did you ever get a grade you disagreed with?
  27. What were the popular fashion trends when you were in school?
  28. How did you study for exams?
  29. Were you ever the new kid in school?
  30. What’s one thing you wish you had done differently in school?
  31. Did you ever pull a prank at school? What was it?
  32. Were there any teachers you didn’t get along with?
  33. What was the first sports event or game you attended?
  34. Did you ever forget your lunch or lunch money?
  35. How did you celebrate the end of the school year?
  36. What was the most interesting thing you learned in history class?
  37. Did you ever take a class just because your friends were in it?
  38. What was the dress code like? Did you ever break it?
  39. Were there any weird or funny school traditions?
  40. What was the most challenging group project you ever had?
  41. Did you have any close calls about missing the school bus?
  42. Were you ever chosen to be a class representative or leader?
  43. How did you handle stress or pressure from schoolwork?
  44. Did you have any pen pals or exchange students in your school?
  45. What was the yummiest thing sold in the school canteen?
  46. Did you ever get an award on field day or sports day?
  47. What types of books did you check out from the library?
  48. Did you ever participate in a spelling bee or quiz contest?
  49. How did you decorate your locker or desk?
  50. What was the funniest thing that ever happened during a school assembly?

Fun Questions About Their First Job

  1. What was your very first job?
  2. How did you get it?
  3. What was your first day like?
  4. Were you nervous? How did you handle it?
  5. What did you buy with your first paycheck?
  6. Did you have a boss who was hard to work for?
  7. What was the funniest thing that happened at work?
  8. Did you make any friends at your first job?
  9. What did you like most about the job?
  10. What did you like the least?
  11. How did you get to work? Bus, bike, or walk?
  12. Did you ever mess up? What happened?
  13. What skills did you learn from that job?
  14. Was the job what you expected it to be?
  15. Did you have a uniform? What was it like?
  16. What were your regular work hours?
  17. Did you ever get a promotion or a raise?
  18. Were there any regular customers that you remember?
  19. What did your parents think of your first job?
  20. What did you do on your lunch breaks?
  21. Did you ever have to work on a holiday?
  22. Were there any office parties or outings?
  23. How did you feel when you left that job?
  24. What was the hardest part of the job?
  25. Did you have any weird or annoying co-workers?
  26. What was your favorite task or duty?
  27. Did you save money or spend it right away?
  28. Was the job close to home or far away?
  29. Did you learn anything that helped you in future employment?
  30. How did that job make you feel about working?
  31. Did you ever have to work overtime?
  32. Did you get any job perks, like free food or discounts?
  33. Was there a company party you remember well?
  34. What was the weirdest request or task you ever got?
  35. Did you ever call in sick when you weren’t really sick?
  36. How did you spend your weekends after getting your paycheck?
  37. Did you ever have a “work best friend”?
  38. Did the job ever interfere with school or your social life?
  39. Did you ever get caught doing something you shouldn’t?
  40. What were your career goals back then?
  41. Were you part of any workplace competitions or contests?
  42. What was the most boring task you had to do?
  43. Did you have to deal with any difficult customers?
  44. What would you do if you had nothing to do at work?
  45. Did you have a mentor or someone who helped you out?
  46. How long did it take you to get the hang of the job?
  47. Was there a goodbye party when you left?
  48. Looking back, what advice would you give yourself at your first job?

Fun Questions About Their Favorite Hobbies

  1. What was the first hobby you ever picked up?
  2. Did you have any hobbies that you’ve since given up?
  3. What’s a hobby you wish you had more time for now?
  4. How did you get started with your current favorite hobby?
  5. Do you have a hobby you do together as a couple?
  6. What’s the most you’ve ever spent on your hobby?
  7. Have you ever won any awards or competitions related to your hobby?
  8. Is there a hobby you tried but just couldn’t get into?
  9. Do you have any hobbies that you picked up from your parents?
  10. What’s the most challenging thing you’ve done related to your hobby?
  11. Have you ever taught anyone your hobby?
  12. What’s the latest hobby you’ve picked up?
  13. Do you have any hobby-related books or magazines?
  14. What’s your dream project or goal related to your hobby?
  15. Do you have a special place at home for your hobby?
  16. What’s the most relaxing hobby you’ve ever tried?
  17. Do you have any hobby-related items on your bucket list?
  18. How has your hobby changed over time?
  19. What’s something you’ve created or achieved that you’re most proud of?
  20. Do you have any hobbies you can only do at certain times of the year?
  21. What’s the most fun you’ve had while doing your hobby?
  22. Do you ever go to events or gatherings related to your hobby?
  23. What’s the most unique or rare item you own related to your hobby?
  24. Have you ever traveled just to pursue your hobby?
  25. How do you stay updated with news or trends related to your hobby?
  26. What tip or hack have you learned that makes your hobby more enjoyable?
  27. Do you have any friends you met through your hobby?
  28. What’s the biggest mistake you’ve made while doing your hobby?
  29. How does your hobby help you relax or relieve stress?
  30. What’s something you wish everyone knew about your hobby?


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!

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Robby Salveron

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.