Grandparents sitting on couch, talking with grandkids
Leah Berenson
Leah Berenson
April 20, 2024 ·  8 min read

20 Insightful Questions to Ask Your Grandkids Before They Grow Up

There’s no denying that, in most cases, grandparents have a powerful bond and influence on their grandkids. In fact, it’s often said it’s a love like no other. In many cases, the same is true for parents and their children. However, as children get older, it can be challenging to find things in common or ways to connect with each other. As a result, conversations become less free-flowing and may take some work. After all, children grow up to be adults, going through several phases during the process. There, their interests, passions, and hobbies change, and life is a never-ending journey of lessons, growth, and new discoveries. To help with that, it’s always good to start the bonding early and to try getting to know your children and grandchildren. To do that, you can ask them questions, but not just any questions will do.

Read: Grandparents May Be Causing Kids Harm With Their Outdated Parenting Beliefs

Asking the Right Questions

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Most often, parents or grandparents ask questions to that may not necessarily get an elaborate answer. Questions like “Did you have a good day?” or “Do you like pizza?” simply get a yes or no, and a please or thank you, depending on the child. Unfortunately, these questions won’t open the path to a conversation. However, according to the New Horizon Academy, a nationally renowned preschool with a solid foundation in “high-quality” and “play-based” curriculum, the answer lies in how you ask the question. For example, instead, you might ask your grandkids what they like on their pizza, or what their favorite part of their day was.

Questions to Ask the Grandkids

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While the main point to asking kids and grandkids the right questions is always to ask something that you would be able to elaborate on, however, the pressure and hope of connecting with kids can get in the way, preventing you from asking the right questions. Here are another 20 questions that are helpful in keeping you strongly connected to your kids and grandkids.

Read: “Granny Pods” Now Allow Your Aging Parents to Live in Your Backyard

1. What Makes You Happy?

Happy Senior Grandfather Talking and Having Fun with His Grandchildren, Holding Them on Lap at a Outdoors Dinner with Food and Drinks. Adults at a Garden Party Together with Kids.
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The late great, Heath Ledger, made a handful of notable statements throughout his career, and one of his most profound related to the fact that no one ever asks you if you’re happy. However, when kids and grandkids are asked what makes them happy, a few really magical things happen. First, their faces will likely light up at the opportunity to share their happiness with the people they love most, bringing both grandparents and grandchildren a sense of joy. Next, they will happily talk about the things that bring them joy, sometimes giving you both a lot to discuss. Last, you can rest easy knowing there are moments and things in the world that make your favorite people, kids, and grandkids happy, even if you’re not always nearby.

2. What Makes You Laugh?

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They say that laughter is the best medicine. It can certainly be helpful for uplifting a mood or creating a happy memory. Therefore, asking your kids or grandkids a question like this will most likely bring both of you some joy while discussing, if not even a few laughs.

Read: The Benefits Of Kids Living Close To Their Grandparents

3. What Makes You Smile?

Smiling cute little african american girl with two pony tails looking at camera. Portrait of happy female child at home. Smiling face a of black 4 year old girl looking at camera with afro puff hair.
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Not only does this question also allow the possibility of sharing a few laughs, but it also cultivates an environment of joy. Therefore, children and grandchildren will feel more comfortable talking to or confiding in you.

4. What Superpower Would You Have?

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This is another fun question that will both give you insight into who your children and grandchildren are, as well as give you both something silly to laugh about together.

5. What is Your Favorite?

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Incredibly, this is a versatile question that can be asked countless times. For example, you might ask your grandkids about their favorite foods, games, sports, colors, outdoor activities, books, movies, music, etc. This is also a great opportunity to hone in on what you and your children or grandchildren have in common, giving you even more to bond over.

Read: Grandmother Rants About Parents Who Treat Grandparents As Babysitters

6. If You Could Be Any Animal, Which Would You Be?

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Questions like these allow for a creative approach to bonding with children and grandchildren because it allows them to play pretend, which isn’t just fun and exciting. It’s also an important part of healthy brain development and is essential for each child to engage in occasionally, if not often.

7. What is a Perfect Day?

happy family grandmother and grandchildren cook in the kitchen, knead dough and bake cookies
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Although the answer may change over the years, asking children this question not only helps you get to know the person they are, but it’ll also give you guidance for cheering them up after a tough day at school or throwing them a surprise party.

8. What Are Your Skills?

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Asking kids and grandkids what they’re good at gives them an opportunity to build self-confidence. It allows them to look within to find opportunities to take pride in their creations, whether pottery, stories, furniture, or computers. Conversing about these skills will also help set children up for success by encouraging them to pursue their talents further.

Read: Grandfather Pens Powerful Open Letter to His Grandkids About Childhood

9. What Do You Want to be When you Grow up?

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Not only is this a great way to help you get to know your kids or grandkids better. It’s also another great way to encourage them to nurture their talents, practice their skills, and pursue their passions.

10. Who is Your Best Friend?

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Asking questions about friends or school peers will help you feel connected and always know what’s going on with your children and grandchildren. To carry the conversation further, you could ask things like “What do you like to do together?” or “Did you meet playing on a (Insert activity) team?”.

11. What is the Best Dessert You’ve Had all Week?

Little happy cute boy is eating donut on blue background wall. child is having fun with donut. Tasty food for kids. Funny time at home with sweet food. Bright kid.
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Children are often food or sweet-motivated. They tend to really enjoy meals and after-meal treats, so much so that they’ll happily talk about those things. Giving grandparents a leg up when planning to surprise their grandkids with sweet treats.

Read: The Love of a Grandparent is One of the Greatest Blessings a Kid can Have

12. Grandkids’ Favorite Magical Creature?

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This is another fun question that helps to encourage imagination and allows adventure to be had no matter where you and your grandkids are.

13. Ask About Silly Songs

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Music is one of the most loved hobbies in the world, be it playing, singing, or just listening. Music is catchy and, in many cases, can be silly or funny. By asking your kids or grandkids about silly songs, you share a moment that may lead to joyous laughter. Additionally, asking children to remember something that happened to them can help them practice mindfulness, as it puts them in touch with a recent memory, locking in that experience. For a longer conversation, you might also try asking your grandkids if they would sing for you or teach you the song.

14. Favorite Places in the World?

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This open-ended question is another great one to ask grandkids because it also does a couple of things. One, it allows them to explore other cultures, foods, and traditions. Second, it allows children to develop an understanding of just how vast and incredible the world is. As well as how different, yet similar, people are no matter their culture.

15. Favorite Memory?

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Although this could’ve been included in the favorite category above, it seemed original enough that it may not immediately pop into your head as one of the questions to ask your children or grandchildren. When you’ve asked all the generic small talk questions, something thought-provoking like this may be just the ticket to bring you and your grandkids closer together.

Read: Family honors grandma’s memory by displaying all of her quilts at her funeral

16. Change the Rules

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Asking kids and grandkids about changing the rules is fun to both see what they prioritize as important and see what they secretly wish they could do differently in their everyday lives. It’s also a fun way to see what kind of leader they would be or will be (because who knows what the future holds).

17. Grandkids Least Favorites

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In contrast to their favorite things, you can ask children and grandchildren their least favorite things as a good way to get to know them while gaining some guidance on what to steer clear of when buying gifts and treats.

18. How Would You Describe Your Family?

Close Up Of Granddaughter Hugging Grandmother In Park
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This is a fun way to see yourself and your children through the eyes of your grandchildren, as well as gain an understanding of the impression that you leave on your family.

Read: Study: Grandparents Who Babysit May Live Longer

19. What Do You Love Most About Being Part of the Family?

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This question can have various answers, from fun weekend trips to the park to helping cook for family meals or holiday get-togethers, or simple things like family game night, reading stories before bed, or the way their siblings play with them and cheer them up when they’re sad. Either way, the answer to this question will undoubtedly warm your heart.

20. What Would You Do with $1,000?

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This is simply a fun and clever way to understand the priorities of your children and grandchildren. After all, it’s very telling of someone’s character when they’re awarded any sum of money. Plus, it’s fun to imagine all the fun things to do with surprise earnings, even if it is pretend.

Although these questions are designed to offer some ideas of insightful questions to help you connect with your kids and grandkids, the best thing you can do is try. Ask these questions, but also take a supportive approach. Stay actively engaged, offer advice when asked for it, and above all else, be encouraging. Another option to take your bonding even further might be to do a fun activity together while having these conversations; this way, the joyous memories will be endless.

Keep Reading: Your Mom May Feel Closer To Her Grandkids Than To You. Here’s Why: Study


  1. 20 Questions to Ask Your Child to Get Them Talking.” New Horizon Academy.
  2. 27 Questions Your Kids and Their Grandparents Need to Ask Each Other.She Knows. Sabrina Rojas Weiss. September 27, 2023.