These 27 Questions Will Get Conversation Flowing Between Your Kids & Their Grandparents

Like other family holidays, Grandparents Day should be one of warm, fuzzy feelings and celebration. Maybe you remembered to send a card and your kids’ artwork. Maybe you’re lucky enough to be able to meet them in person. Or maybe the celebration is going to consist of a couple of cross-country FaceTime calls, which, let’s face it, can be agonizing and awkward a lot of the times. That’s why we’ve decided to help you, your parents, and your kids with some questions to ask each other to get the conversations flowing.

Having grown up across the country from my own grandparents, I well remember the discomfort of being forced to talk on the phone to them. I loved them, and our in-person visits were always fun, but on the phone there were a lot of one-word answers on my end and extended silences on theirs. We just simply didn’t know what to say to the other generation. And now I often see that happen with my own son, my dad, and my in-laws. Only with great effort on their part do they struggle past the monosyllabic responses and get into an in-depth discussion about ice cream flavors or which L.O.L. doll has the best hair.

As a reporter for more than half of my life, I do know a thing or two about getting people to talk. Every once in a while, I’ve managed to use that skill in starting a conversation with someone in my personal life too. And I’m not the first person to realize that this is a way for generations to reach out to each other. StoryCorps, the nonprofit dedicated to recording the stories of everyday people, has long recommended that people interview their own family members to connect and to preserve their memories for posterity. For-profit companies and others have followed suit. With their help, I’ve gathered some questions your children and their grandparents can use to talk to each other, in person, on the phone, or via video chat.

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Two tips that every reporter learns early on: 1) Don’t as “yes or no” questions — unless you’re ready with a quick “why” follow-up. 2) Automatic questions (“How are you?”) get automatic replies (“Fine”). But when you reword those to be just a little more specific — i.e. “What did you have for breakfast?” “What are you looking forward to doing today?” — you get real answers.

Questions from kids for grandparents:

  • What is the best meal you’ve had this week?
  • What was your favorite food when you were my age?
  • What does the sky look outside the window right now?
  • When you were a kid, what did you do on rainy or snowy days?
  • What did you watch on TV last night?
  • What was your favorite TV show when you were little?

From StoryCorps:

  • What was my mom/dad like growing up?
  • Do you remember any songs that you used to sing to her/him? Can you sing them now?
  • Was she/he well-behaved? What is the worst thing she/he ever did?
  • Who were your favorite relatives?
  • What were your parents like?
  • What were your grandparents like?
  • Do you remember any of the stories your grandparents used to tell you?
  • Do you have any favorite stories from school?
  • What do you feel most grateful for in your life?

From story-sharing app OneDay:

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  • What parts of your life helped shape you as a person?
  • What was a historic moment that you lived through? Can you tell me about it?
  • Do you have a favorite age/stage of your life?
  • How has the world changed during your life?
  • What tradition of yours do you hope our family continues?

Questions from grandparents to kids:

  • What has been the best dessert you’ve had all week?
  • Who is your best friend? What do you two do together?
  • Who is your favorite TV show character?
  • If you could be any animal, what would you be?
  • If you could be any magical creature, what would you be?
  • Have you heard any silly songs lately? Would you sing them?
  • Which superpower would you rather have, invisibility or flight?

Do something while you talk

Some kids are going to be shy no matter what you ask, so you can switch up the format a bit and have them do something while they talk.

“Activity is what brings generations together,” Donna Butts, executive director of the DC nonprofit Generations United, told National Geographic. “They bond more quickly around a project, something that both can create or solve and do together.”

Technology means that even if grandparents and children are in different parts of the world, they can still do something together. The video chat app Caribu can help a grandparent read to a younger child, play games with them, and even draw together. And the meal kit company Raddish Kids has step-by-step instructions for baking together via Zoom call. For a really in-depth project, you can also print out a family tree for them to fill out together (they even have adoptive family trees!).

It’s OK to admit that relationships between children and their grandparents sometimes need a little nudge to flourish. If you can help them along, you’ll feel the benefits for years to come — maybe even when you’re a grandparent yourself, too.

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These celebs are sharing their thoughts and feelings on what it’s like to be grandparents.

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