by Jay Payleitner
Adapted from his book, Hooray for Grandparents!

As grandparents, we want to share our values and life lessons with our grandkids. It’s an important part of our role.

But how can we do that without being preachy?

There are lots of resources out there that list questions to ask young people. As grandparents, we should do that.

  • Open-ended questions.
  • Questions that require specific answers.
  • Questions that test their knowledge.
  • Questions that get them laughing.
  • Questions that get them thinking.

Here are some to get you started.

But I get even more excited about questions designed to get you telling stories that your grandchildren need to hear.

Below are 12 of those questions, and here’s the idea: Give this list to a grandchild and have them choose one to ask you. Suddenly you will be sharing stories and life lessons they want to hear … and need to hear. Go ahead. Try it and see how it works. This interaction works on the phone, over Zoom, face-to-face, in the car, with one grandchild, or with an entire gaggle of grandkids surrounding you.

12 Questions Your Grandkids Can Ask You!

1. What was unusual about the town or neighborhood in which you grew up?

2. Who was your best friend at every age level? How did you meet? Are you still friends?

3. Did you have a favorite hangout? A building, park, shopping mall, woods, or vacant lot?

4. Were you ever rushed to the hospital, sent to the principal’s office, or stopped by a cop?

5. What was your first job? Best job? Worst job?

6. Did you have a nickname? What was your reputation?

7. What was your favorite subject in school? What did you want to be when you grew up? 

8. What was your favorite book, movie, television show, or music group, or board game?

9. What was your best or worst road trip or vacation?

10. Who was your first boyfriend or girlfriend? How did you meet? When was your first kiss?

11. What is your biggest disappointment or regret? Did you ever lose a friend over something you regret?

12. What’s something you did that you never told your parents about? 

Please let us know how it goes. You can leave a comment on the Grandkids Matter Facebook page here. But most of all, enjoy that time with your grandkids. You’re building bonds, sharing your heritage, and surely bringing them a dozen other benefits.

Read more from Jay at Grandkids Matter here.


Jay Payleitner is a best-selling author of Hooray for Grandparents! and more than a dozen other books on marriage, family, and doing life right, including 52 Things Kids Need from a Dad, 52 Ways to Connect as a Couple, and What If God Wrote Your Bucket List? His weekly podcast is called, “Getting Life Right.” He and his wife, Rita, live near Chicago, where they’ve raised five great kids (and now have eight grandkids) and have loved on ten foster babies. For information on booking Jay to speak at your next event, visit