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10 Questions To Ask Your Grandparents on Grandparent’s Day & Beyond

Written by John Shallman, Author of Return from Siberia (Skyhorse Publishing. August 18, 2020)

Photography by Photo by Serena Burroughs

Grandparent’s Day happens on the first Sunday of September after Labor Day—which means this year Grandparent’s Day is on September 11, 2022. Even if you haven’t planned anything special, it’s a good reminder that the best grandparents deserve to be celebrated year-round. Which is where this list of great questions to ask your grandparents comes in.

“If you are lucky enough to have living grandparents—or great aunts and uncles, elderly parents, even elderly friends—you have exclusive access to living history,” says John Shallman, author of novel Return from Siberia—the story of one family’s journey to gain knowledge of its past and how it impacts their lives.

“The older folks in your life are vast reservoirs of incredible wisdom, earned from simply surviving the not-so-distant past. Each of them have firsthand accounts of those trying circumstances and historic events you’ve heard of but thought you’d never experience yourself,” Shallman continues. “However, when you ask any or all of these questions to your grandparents and allow yourself to imagine life as it was in their shoes, you are taking one giant step into their lived history—a history that has far more to do with you than you might think.”

Below, Shallman shares 10 questions to ask your grandparents, on Grandparent’s Day, or beyond!

1. What is your earliest childhood memory?
This will tell you a lot about the world they were born into. Maybe your grandma recalls her parents arguing in their native tongue about groceries at the height of the Great Depression as a toddler; and maybe your grandparents can’t recall anything at all before the peace and love they found at Woodstock. Whatever that earliest memory may be, it will certainly be illuminating.

2. What did society look like growing up, and what were the big moral questions being asked?
Just as we are living through an historic crisis that will alter the course of history, so too did your grandparents. The Great Depression, World Wars, assassinations, the Civil Rights Movement, technological advances—they each lived through historic shifts in the fabric of society and lived through the changes, with roles to play and difficult decisions to make. What were those roles and decisions? How did they shape the world-views they hold today both politically and economically?

3. What were your parents’ names and what were they like?
Our parents had parents, who had parents with parents… How far back can we go? What were they all like? And while we’re on the subject…

4. Are there any traits—good, bad, physical or psychological—that run in our family?
It may be your sea blue eyes, or a fiery temperament; it could be a passion for singing, a penchant for the drink or a particularly…excitable stomach. Every family has shared traits, one of many ways we are connected to the people who came before us. Your grandparents’ insight into the past may be loaded with insight into yourself.

5. Which places in the world have the most significance to you, and why?
As the Beatles’ song goes, “There are places I’ll remember/ All my life, though some have changed…” Everyone has places with particular significance, changed or unchanged by the passage of time. What are your grandparents’?

6. Of all the hardships in your life, what was the most challenging obstacle you’ve faced, and how did you get through it?
What were the life-changing moments of your grandparents’ lives? How did the past prepare them for the often frightening present? Sometimes we have to look at our parents’ and grandparents’ lives as lessons. How can their past experiences help us get through today’s crises?

7. Is there anything you wish you could have done, or done differently?
It’s nearly impossible to live a life without regret, and our regrets inform our choices and our values. Again, this is a teaching moment—listen closely. In that same vein…

8. What are the hopes you have for your family?
The dreams we have of our own sometimes become the dreams we hold for our children. What is it that your grandparents hope for you?

9. What has brought you the most joy in your life?
Explore their passions, projects, skills, and stories. Celebrate their lives by reliving their favorite moments.

10. Do we have any family heirlooms, photographs, artwork, letters, diaries or manuscripts? Are there any stories behind them?
While listening to your grandparents’ recollections is precious, there is no substitute for a real time account of those experiences. I was lucky. I discovered a 100-year old autobiography written by my grandfather who was a revolutionary in Russia exiled to Siberia by the last Czar of Russia. I never met my grandfather, but his extraordinary life was so vividly documented that I had to write a book about the impact his story had on my life and the lives of every member of my family. The true story documents an extraordinary time of political upheaval in Russia and Europe just prior to World War I, while also drawing parallels in current day American politics and the current philosophical and ideological debates about immigration, Democratic Socialism, and Capitalism. Beyond the deep social, political and philosophical themes, I found romance, adventure, betrayal, suspense, and the struggles of families trying to find the American Dream—yesterday and today.

Want more Grandparents Day activities and ideas? Here are 15 ways to nurture relationships between children and grandparents during a pandemic—perfect for Grandparents Day 2022!


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