11 Questions to Ask Your Grandparents Before It’s Too Late

Katie Sweeney

At age 33, I feel lucky to have two healthy and active living grandparents I see on a regular basis. I am even more fortunate that I have an exceptional relationship with one of them, my paternal grandfather, Al. Equal parts Fred Astaire and Frank Sinatra with a dash of Pinocchio mixed in for good measure, Al is the patriarch of our family who regularly hosts everyone—cousins, aunts, uncles, friends—at his house on Sunday afternoons. We hang out by the pool, drink chardonnay, barbecue steaks and potatoes, and, most importantly, swap stories. All of us grandkids love asking Al questions about the past. Not only have we heard about personal and national history (my grandmother brought her children to Dr. Martin Luther King’s wake in Atlanta—how cool is that?), but we’re also learning valuable life lessons. If you have the opportunity to spend time with your grandparents, then I’d encourage you to sit down and ask them the following questions.

1. How did you and Grandma/Grandpa meet?

Even if one of your grandparents is deceased, the living grandparent will most likely lovingly remember how he met your grandmother, or vice versa, all those years ago. I always enjoy hearing how couples met, and it’s more significant when it’s someone directly in your ancestral line. If they are into the story, find out how they got engaged and what their wedding day was like.

2. What happened the day Mom was born? What happened the day I was born?

Birthing stories are always fun! Was there an exciting rush to the hospital? Was your grandmother certain it was going to be a boy, but it was a girl? This is a good question for a big family meal when generations are together, because everyone can tell their sides of the story. While your grandparents will only be able to tell what happened the day your parents were born, your aunts and uncles will be able to recount what happened on the day you were born.

3. What was your initial opinion of my dad when he started dating my mom?

Or vice versa. Whether or not your parents are still together, it’s interesting to hear what your grandparents’ gut instincts were about them as a couple. Did they know right away he was the one? Did they think it would never last, but it did?

4. What was it like to live through the wars and the civil rights movement?

From World War II to walking on the moon, many significant moments in American history happened during our grandparents’ lives. What was it like to live during the Vietnam War? Where were they when they found out JFK died? It’s fascinating to hear these stories from your loved ones who lived through them. Chances are they will enjoy telling you too!

5. What do you miss about the good old days?

Your grandparents likely have a fond nostalgia for their days of youth, be it for technology-free communication or the way their hometown looked without skyscrapers. It’s exciting to see their faces light up when they take a trip down memory lane. I love hearing how people in my parents’ generation made plans and communicated, because it seems almost impossible in our modern-day lifestyles. Al’s explanation goes something like this: “You would call a landline and say, ‘Let’s get lunch at this restaurant at this time next week,’ and then you would go to that restaurant and have lunch next week with your friend.” It sounds simple, but it’s mind-boggling! What if something came up? What if you were running late?

6. What is your philosophy on life?

Older people are wiser, and grandparents are the wisest of them all. Ask your grandpa and grandma what philosophies they have practiced throughout their lives, and try and incorporate them into your life. Al writes his philosophies on index cards and tapes them to mirrors and cabinets in his house. Some that have resonated with me are “Intend to allow more joy into your life—amen!”, “Singing keeps you young”, and “This moment is as it should be.”

7. Do you have any major regrets?

Many people live their lives with a “no regrets” attitude, but almost everyone can look back and say “I wish I had not done this” or “I wish I had done this.” It’s intriguing to learn what your grandparents regret, and doing so may even lead you down a path you hadn’t considered.

8. What are you most proud of?

This one is pretty self-explanatory. Find out which accomplishments your grandparents are most pleased by. If the conversation is captivating, also ask what are they most grateful for. You might be surprised by their answers.

9. How do you want to be remembered?

Most people want to be remembered in a positive light, but for what? For being a wonderful father? An amazing cook? A great golfer? How do your grandparents want you to see them? If you see them that way, make sure they know it.

10. What have you not done that you still hope to achieve?

Just because they are old doesn’t mean that they can’t have life goals! Whether they want to start an Instagram account and build a following or they want to spend two months practicing French in Paris, your grandparents still have hopes and dreams they wish to achieve. Find out what they are, and then do your best to help them reach the goal.

11. If you could change one thing about modern society today, what would it be?

Do they wish young people would stop spending so much time on their phones? Do they wish people would slow down more and appreciate the little things in life? What do they not like about modern society, and what would they do to change it?

Kick off the conversation with some tea and cookies—below!

Do you have a good relationship with your grandparents? What have they taught you?

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