20 Questions to Ask Elderly Loved Ones to Connect and Reminisce

Growing up, I only saw my grandparents twice a year and would beg to hear their stories whenever I got the chance to be with them. My grandfather was candid and loved to laugh about his wild misadventures, like being stuck on top of a train car during the great Kansas City flood of 1951. Or how, when he was in his 20s, he drove Elvis Presley through Germany.

My grandmother was more demure, preferring to tell stories about my mother and uncles, but only when prompted. At 16, she was crowned the Watermelon Queen of Georgia and had her picture taken with the mayor in a dress she sewed herself.

I wouldn’t have known any of these unique stories had I not asked questions, and knowing what questions to ask elderly loved ones isn’t always easy. Here are some interesting topics to talk about with seniors and questions to help you bridge the generational gap with your older loved ones.

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• What do you remember about the place you grew up? Do they still live there, or have they visited? If so, how has it changed?
• Which invention from your lifetime are you most amazed by? What was life like before? Their generation witnessed the invention of color TV, personal computers, the Internet, and more.
• What’s the weirdest fad you remember? Is it swallowing goldfish, pet rocks or Jell-O™ salad? How about expressions or slang?
• What was your favorite movie when you were younger? Suggest watching it together! Streaming services like Turner Classic Movies and Criterion Collection offer large selections of old films, as do many local libraries.
• What was your first job? How about your favorite? My grandfather worked in a prison for 12 cents an hour!

• Do you know the history of your family name, crest, or origin? If they’ve always wanted to learn more, suggest a service like Ancestry to use together. You may be surprised by the results.
• What do you remember about your parents and grandparents? This is a special opportunity to learn more about family members you didn’t have the chance to meet.
• What were your children like growing up? Do they have any funny or embarrassing stories about Mom or Dad?
• What did you and your siblings do for fun? Maybe straight-laced Aunt Ruth was a huge troublemaker back in the day!
• How did you meet your spouse? Was it love at first sight or an uphill battle? What was the wedding like?

• What are the most rewarding things about getting older? Is it a lifetime of knowledge? The senior discount at the movie theatre?
• What are the most important lessons you’ve learned in your life? Ask to hear the stories behind those lessons.
• Who has influenced you the most? Thank your loved one for the ways they’ve influenced your life so far.
• What life advice would you pass along? Take this answer to heart.
• If you could go back to any age, what would it be? Would they stay the age they are now or go back? How far back? What was life like at that time?

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• What was the best day of your life? It could be a wedding, the birth of a child, or just a nice day by the lake.
• What are you the most proud of? Congratulate them on this accomplishment.
• What kinds of things make you the happiest now? Now that you know, you can try to make them happen often.
• How have your dreams and goals changed throughout your life? Do they seem at peace with these changes, or do they have regrets?
• How would you like to be remembered? This question can be sad, but knowing how your loved one wants to be remembered will help you honor them and tell their story.

Older generations have a wealth of information and stories to share. You can use these questions as a starting point for a conversation, but you don’t have to ask them all at once. Next time you visit an aging parent or grandparent, take the time to listen and connect. Whether you casually discuss topics while doing activities together or use the list as interview questions for aging family members, you’re sure to learn something new.

Write down the answers, record them on your phone, or just chat over a cup of coffee and share experiences. Learning more about your loved one’s life can lend you stories to tell for generations to come.