Rewind and Reveal: 12 Questions to Ask the Grandkids Before the Year Ends

What?! It's December already! Where did those last 11 months go?

I know, I know, it happens every year—December sneaks in wearing a cozy sweater and carrying a mile-long to-do list. While our world rushes toward year-end sales, holiday menus, and half-finished resolutions, I have been thinking about what to do differently with my grandkids.

We could talk about homemade gifts and gingerbread houses, which we do every year. But what I really want to know from him is what made his heart beat faster this year? What did he learn? What does he hope for?

As Intentional Grandparents, my sisters and I have spent the year unwrapping some serious topics like how to help kids learn, activities to connect them with us, and how to rewire our circus. But not all topics have to be serious, somber, or only thought-provoking. It can be playful, surprising, and deeply connecting—especially when shared across generations.

So here it is, my year-end tradition in the making: 12 questions I will ask my grandson before the calendar flips. Now, it won't work if we tackle them all at once. So, I am thinking of some over a FaceTime call, maybe during my Christmas visit while making pancakes, or driving to soccer, or maybe instead of a bedtime story.

12 Questions

1. What was your favorite day this year, and why?

Simple, yes, but this question opens the door to small, beautiful memories we may not know about. I think it will help them think about what brings him joy—and lets us see his world from the inside out.

2. What's something new you tried this year?

This one will be interesting since I'm not around their world every day. It could be sushi, speaking up in class, or maybe a new sport.

3. What's a book, show, or song you really loved this year?

Chances are, he will probably say things I haven't read or seen, but pop culture is a window into their current interests. I know that at 4, my grandson was all about dancing Naatu-Naatu. What this year brings should be just as expanding to my life. Of course, now that he is older, I am determined to watch, read, or listen along with anything he shares. Stay tuned for what I learn.

4. What's something you wish grown-ups understood better?

Now this one... whew. I am going to be sure this one takes place just between us, and I will need to be ready to listen without correcting or defending. It will be a gift to hear how kids perceive the world—and how we can do better by them.

5. What was something that made you feel really proud of yourself?

I think he will like this question, so I am going to let him brag. In fact, whatever he says, I will celebrate it. Pride builds confidence, and asking about this shows that we notice their efforts, not just their results.

6. What was hard for you this year?

Kids carry invisible backpacks full of feelings. My goal is to give him space to share a struggle—without trying to fix it—teaches emotional intelligence and resilience.

7. What's something that made you laugh so hard you snorted?

He's a typical boy, and I am sure that by just saying "snorted" as I ask the question will bring uncontrollable giggles. Giggles are glue. Now, that's what family stories are made of!

8. If you could relive one moment from this year, what would it be?

If this one doesn't come easily to 'em, it'll give me an idea to plan something memorial before the end of the year, or if he has something, we can recreate that moment together.

9. What do you hope happens next year?

This is where dreams start. He may say, "I want a dog," which is a strong possibility. Or, with him heading to kindergarten, he might whisper, "I hope I make a new friend." Either way, I'll get a glimpse of what matters most to him.

10. What's something you'd like to learn next year?

This opens the door to new adventures—maybe even something we can do together. (Pickleball club, anyone?)

11. Who is someone you admire—and why?

Hmmm… I'll be ready for various answers from "Taylor Swift" to "my baby sister." Seeing who their role models are will offer insight into the values they're building.

12. What's something we did together this year that you really liked?

This question is a little magic mirror—it'll show me what matters most about our relationship in his eyes. Spoiler: It's rarely the "big" stuff. It's the small, steady, silly, sacred bits.

Why These Questions Matter

As grandparents, we have a unique role. We are the memory-keepers, the slow-down-and-listen people. When we ask thoughtful questions, we invite our grandkids to reflect—but more importantly, we show them they matter. Their voices, thoughts, and experiences matter—not just to their teachers or parents but to us—the ones who cheered when they took their first steps and are still cheering now.

I am hoping that these questions will be more than just conversation starters. I see them as relationship builders, a soft landing at the end of a big, busy year, and a chance for us to rewind together.

Remember, your grandkids may not remember every gift you gave or every cookie you baked. But they will remember how you made them feel: seen, heard, and wildly loved.

Want to Make It a Tradition?

There is no one "right" way to ask the questions. Here are a few ideas that might spark an idea:

1.    Create a "Year-End Reflection Jar." Print or write the 12 questions on slips of paper. Let your grandchild pull one out at a time during a visit or video chat.

2.    Make a keepsake book. Write down their answers and return them to them at graduation, or just reread them together next year.

3.    Use Voice Memos or video. Record their answers and save them in a digital "Grandkid Time Capsule."

However you do it, just do it. Make reflection part of your family rhythm—not a chore, but a gift.

Because time passes quickly, and December, with all its chilly days and warm hearts, is the perfect moment to pause... and ask, "Hey, tell me about your year."

So here's to asking better questions—and getting to know those wild, wonderful grandkids just a little bit more before the year slips away.