75 Questions to Ask Your Kids Every Year

Asking the same thoughtful questions every year creates a living time capsule of your child’s personality, interests, and dreams. Whether you record answers on birthdays, during the first week of school, or while MileSmile reads prompts through hands-free Car Mode on the way to Grandma’s house, these 75 questions spark meaningful conversations that your future self will treasure.

Why Repeat the Same Questions?

  • See growth: Answers reveal how perspectives shift as kids mature.
  • Create rituals: Shared traditions build security, especially during annual road trips.
  • Boost communication: Conversation prompts help even quiet kids open up without pressure.
  • Capture memories: You get ready-made quotes for photo books, birthday slideshows, or graduation gifts.

How to Use These Prompts

  1. Pick your moment: Annual road trip kickoff, first-day-of-school breakfast, or New Year’s Eve reflection all work beautifully.
  2. Choose a format: Record answers in a shared journal, voice memo, or MileSmile note so you can revisit them next year.
  3. Let Car Mode guide you: Queue the questions in MileSmile and have the app read them aloud while you keep your eyes on the road.
  4. Celebrate change: Compare this year’s responses to last year’s and point out new skills, interests, and confidence.

Annual Question Tracker

MomentBest SettingSuggested Sections
Birthday weekBirthday breakfast or bedtime chatFavorites + Family & Friends
Summer road tripHands-free in Car ModeAdventures + Hypotheticals
Back-to-school seasonDrive to school or Sunday planning meetingGrowth Reflections + Big Feelings
Year-end reflectionFamily sleepover in the living roomHighlights + Future Dreams

15 Favorite Things Questions

  1. What is your favorite thing about mornings right now?
  2. Which snack can you never get tired of?
  3. What song makes you want to dance immediately?
  4. What book, comic, or podcast are you into this year?
  5. Which MileSmile game mode do you want to play first on a road trip?
  6. What outfit makes you feel unstoppable?
  7. What movie line do you quote the most?
  8. What smell instantly makes you happy?
  9. What animal do you feel most like this year?
  10. What emoji describes you right now?
  11. Which dessert deserves a holiday named after it?
  12. What outdoor place feels like “yours”?
  13. What video or board game do you want everyone to play with you?
  14. What part of the day should last longer?
  15. Which conversation starter should MileSmile add next?

15 Growth Reflection Questions

  1. What new skill did you learn this year that surprised you?
  2. When did you feel really brave?
  3. What is something you understand now that you did not last year?
  4. Which challenge felt hard but turned out to be fun?
  5. What did you do this year that made someone else smile?
  6. What habit are you proud of sticking with?
  7. When did you help someone without being asked?
  8. What question do you hope future-you can answer?
  9. When did you feel truly listened to?
  10. What is a mistake you grew from?
  11. What made you feel calm during stressful days?
  12. Which family rule makes sense to you now?
  13. What did you appreciate about your teachers, coaches, or mentors?
  14. What was your biggest “aha” moment?
  15. What superpower do you think you are developing?

15 Family & Friends Questions

  1. What is your favorite thing we did as a family this year?
  2. Who made you laugh the hardest?
  3. What is a new inside joke we should never forget?
  4. Which friend do you want to invite on our next MileSmile-powered road trip?
  5. Who do you wish lived closer?
  6. What is one way our family could be even kinder to each other?
  7. What makes you feel most supported by us?
  8. Who would you like to interview with these questions next?
  9. What family tradition should we start this year?
  10. Who do you admire outside our family?
  11. When do you feel most connected to your siblings?
  12. How do you like to show appreciation for people you love?
  13. What advice would you give parents to understand kids better?
  14. What chore would you gladly trade with someone else?
  15. Which car games bring out the best in our crew?

15 Adventure & Hypothetical Questions

  1. If our car could teleport, where would we go first?
  2. What destination should be our next epic drive?
  3. If you designed a roadside attraction, what would visitors do?
  4. Which fictional character would you want as a travel buddy?
  5. If you could swap places with anyone for a day, who would it be?
  6. Which future invention do you hope exists before your next birthday?
  7. If you could rename our vehicle, what would you call it?
  8. What mystery would you like MileSmile to solve for you?
  9. If you built the perfect snack stop, what would it sell?
  10. Which national park or landmark are you curious about right now?
  11. If we made a family playlist, what three songs must be on it?
  12. Which state license plate design is the coolest?
  13. If you could create a holiday, how would people celebrate?
  14. What wild roadside animal sighting would you love to witness?
  15. If we turned our stories into a podcast, what should it be called?

15 Big Feelings & Future Dreams Questions

  1. What is something you want to feel more often next year?
  2. How do you calm yourself when big feelings show up?
  3. What do you hope your friends remember about you?
  4. What are you curious to learn next?
  5. Which goal would make you fist-pump if you accomplished it?
  6. What kind of person do you want to be known as?
  7. What does your dream road trip include?
  8. How can our family support your biggest wish right now?
  9. What courage do you want to practice?
  10. What would make this year feel legendary?
  11. What does “home” feel like to you?
  12. What would you like to try that feels a little scary?
  13. What is one word you want to guide you this year?
  14. What do you want to ask future-you one year from now?
  15. How will you celebrate when you hit your next milestone?

Turn Your Answers into a Family Highlight Reel

Save your responses in MileSmile, capture audio clips with the app running in Car Mode, or compile them into a digital scrapbook. Replaying these answers during future trips reminds kids how far they have come and keeps everyone excited for the next round of questions.

Keep the Conversation Going with MileSmile

When you want fresh prompts beyond this annual list, open MileSmile for unlimited AI-generated games, trivia, and dares tailored to every passenger. Car Mode handles the narration and steering wheel controls so you can prioritize eye contact, laughter, and the open road. 

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