Summary: Day 4 Challenge Instructions

Contact an older relative by phone and ask if they have 30 minutes for a call.  They’ll love the opportunity to connect especially during this time of self-quarantining.

You can also do this challenge with an older friend or neighbor if you’re unable to connect with an older relative.

Ask them 10-20 questions.  You can use the questions below as a guide or feel free to create your own. 


  1. How did you meet my father/grandfather, mother/grandmother, uncle/aunt, etc?
  2. What special traditions did you have in your household growing up?
  3. What was your favorite t.v. show as a kid?
  4. Name an object from your childhood that you still own.  What’s the story behind it, and why have you kept it.
  5. If you could relive one memory just for fun, what would it be?
  6. What’s your biggest regret?  For example, if you could go back and make one decision differently, what would it be?
  7. What’s the greatest life lesson that you can share?
  8. What person comes to mind when you hear the word “hero.”  Why?
  9. What has been your favorite vacation and why? 
  10. Who was your best friend growing up and now?
  11. When you were in high school, what did you want to be “when you grew up?” What path did you ultimately choose and why
  12. What issues in the world were most important to you growing up?  What about now?
  13. What’s your favorite food and why?
  14. If you have children, name each of them and describe their personalities when they were young.
  15. Who was the most famous person you ever met and where did you meet them?
  16. If money were no object, describe something you would have done or tried in your life that you didn’t.  Describe why you chose that “something.
  17. Name one person from your whole life who made you laugh the most.  Describe what that person did that was funny, and tell a story that always makes you smile. 
  18. What is your favorite memory of me and why?
  19. What has been your greatest fear and what did you do about it?
  20. What was your favorite book, song, author, artist, actor, etc?
  21. What’s something about you that I don’t know?

Oh no…you ran out of questions?  Keep going and just ask them whatever comes to your heart.

Note: Questions adapted from “The Story of My Life” journal by Piccadilly.


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