55 Questions to Get to Know Your Grandkids on a Deeper Level

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You know your grandchildren better than anyone.

You know their favorite color, their least favorite food, and what they like to watch/listen to/read when they are in need of comfort. 

You know them front and back… Right?

While you know the ins and outs of your grands better than most, there are still ways to get to know them even better, beginning with these 55 questions that will engage them on a deeper level:

Grandma, granddaughter, and dog on the couch
  1. What makes you happy?
  2. Can you tell me about your best friend?
  3. What’s your favorite subject in school and why?
  4. If you could change one thing about the world, what would it be?
  5. What is your dream job, and why?
  6. What is the most challenging thing you’ve ever done?
  7. Can you tell me about a time you were really proud of yourself?
  8. What do you think makes a person good?
  9. What’s the most adventurous thing you’ve ever done?
  10. Is there a book or movie that has changed how you think about things?
  11. If you could go anywhere in the world, where would it be and why?
  12. Can you tell me about a time when you helped someone?
  13. Who is someone you admire and why?
  14. What’s your favorite thing about yourself?
  15. Is there a time you made a mistake and learned something from it?
  16. If you could have a superpower, what would it be and why?
  17. How do you handle it when you’re feeling sad or upset?
  18. What do you want to be remembered for?
  19. What’s your favorite memory of us together?
  20. What are some things you want to learn more about?
  21. Can you tell me about a time when you felt really brave?
  22. If you could meet anyone in the world, who would it be and why?
  23. What do you feel most grateful for?
  24. What are your favorite hobbies?
  25. How do you like to express your creativity?
  26. What’s something that scares you, and how do you deal with it?
  27. What’s a goal you have for the next year?
  28. Can you tell me about a time you disagreed with a friend and how you handled it?
  29. What’s something that makes you unique?
  30. What does your perfect day look like?
  31. What are some things you’d like to change about yourself and why?
  32. Can you tell me about a time when you felt misunderstood?
  33. What’s a question you’ve always wanted to ask me but haven’t yet?
  34. What’s something new you’d like to try?
  35. What do you think are the most important qualities of a friend?
  36. What’s the best piece of advice you’ve ever received?
  37. How do you define success?
  38. What’s something you wish adults understood better about your generation?
  39. What is your biggest fear about the future?
  40. If you could invent something to solve a problem, what would you invent?
  41. What’s something you’ve done that you never thought you could do?
  42. How do you handle disappointments or setbacks?
  43. What is your favorite family tradition and why?
  44. What is something you’re looking forward to?
  45. How do you decide if you can trust someone?
  46. What’s the most valuable lesson you’ve learned so far?
  47. Can you tell me about a time when a friend made a big difference in your life?
  48. What makes a house feel like a home to you?
  49. What’s something you’re really good at, and how did you get good at it?
  50. If you could speak to everyone in the world at the same time, what would you say?
  51. What is something that you believe in strongly?
  52. How do you handle it when someone hurts your feelings?
  53. If you could have any animal in the world as a pet, what would it be and why?
  54. What’s a big dream you have for your life?
  55. How would you describe yourself in three words?


I hope these easy yet thought-provoking questions help you get to know your grandkids on a deeper level. They may not realize it, but by answering, they give us (and them!) an even better look at who they are as people. Enjoy – and God bless!

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