Family & Relationships

20 Questions to Ask on Grandparents Day

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Remember the old game, 20 questions? Well we’ve got an idea.

September 10—the first Sunday after Labor Day—is National Grandparents Day. It’s a great time for older adults to connect with the younger generations, and vice versa. It’s a day to appreciate and learn from our elders.

We’re challenging our readers and their families and friends to play a game of 20 Questions: Grandparent Edition. It goes like this: First, the younger person can ask the following questions of the older person, and then, the older person can turn the tables and ask the younger person. Everyone plays!

Of course, not everyone has a grandchild or a grandparent, but everyone has the opportunity to reach out across the decades and ask about another’s experience. So find someone in a different age bracket than you and start asking. You never know what you might learn, whether it’s someone inside your family or beyond.  

Here goes:  

  1. When were you born?
  2. Where were you born?
  3. What do you know about the day you were born?
  4. What is your earliest memory?
  5. What was your favorite toy?
  6. What songs or musical artists did you love as a child?
  7. Think about your mom baking. What smells come to mind?
  8. Did you watch television as a child or listen to the radio? (What shows?)
  9. What was your favorite and least favorite subject in school?
  10. What were your mom and dad like?
  11. What did you want to be when you grow up?
  12. What was your favorite dinner as a kid?
  13. What did you do for fun?
  14. What kinds of activities did your family do together?
  15. Who was your best friend growing up?
  16. What was invented in your lifetime that made a difference?
  17. What is a moment you’ll never forget?
  18. What is a lesson you want to share with me?
  19. What are you most proud of in your life?
  20. What’s something that I don’t know about you?

This list just a start of what will hopefully be an ongoing conversation. Feel free to supplement with your own questions. If you’d like to take it a step further, grab a tape recorder or download a recording app and preserve the conversation for your grandchild to keep. It could be very meaningful one day.  

What do you wish you’d asked your own grandparents? Share it with us, we’d like to know!

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