20 Questions to Ask Older Loved Ones to Connect & Reminisce

March 8, 2022 at 3:00 p.m.


Writer Claire Samuels loved it when her usually demure grandmother told stories about her life, including the time when, at age 16, she was crowned the Watermelon Queen of Georgia and had her picture taken with the president in a dress she sewed herself.


Samuels wouldn’t have known this or other unique stories about her grandparents if she had not asked the right questions. Knowing what questions to ask isn’t easy, she advises, but she suggests some interesting topics as idea-starters that may lead to meaningful conversations with your older loved ones.


Questions about when they were young:

  • What do you remember about the place you grew up? Perhaps they still live in the same town or have visited.


  • Which invention from your lifetime are you most amazed by? Their generation witnessed the invention of color TV, personal computers, the Internet, and more.

  • What’s the weirdest fad you remember? How about expressions or slang?


  • What was your favorite movie when you were younger? When you find out, you can 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 job?

Questions about family

What do you remember about your parents and grandparents? It can be especially meaningful 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 your Mom or Dad?

What did you and your siblings do for fun? Maybe you’ll learn that 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?

Questions about getting older

What are the most rewarding things about getting older? Is it a lifetime of knowledge, or maybe even something as simple as senior discounts.

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? What was life like at that time?

Questions about values

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 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? It’s okay to discuss the difficult things too.

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.


The Legacy Project offers a longer list of questions to ask grandparents and other aging loved ones in your life, as well as activities to help your aging relatives recall and share their life stories. Whether you write down these answers, record them on your phone, or just take the time to connect, learning more about your loved one’s life is good for you both. This article is courtesy of www.aplaceformom.com


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