60 Questions You Can Ask Your Grandchildren

grandpa and grandson reading on a picnic

Grandparents are often the wise, fun-loving authority figure in the lives of their grandchildren. 


Especially when the grandkids are young.


And what better way to keep that connection strong than by getting to know them better?


But how do you find questions to ask your grandkids that are both meaningful and fun?


Whether you’re nearby or a long-distance grandparent, here are 60 questions to ask your grandchildren. 


May you start meaningful conversations, get those creative juices flowing, or just have a good laugh together.


Table of Contents hide
3 Questions to Ask Older Grandkids

Questions to Ask Your Under-5-Year-Old Grandchildren

questions to ask your under-5-year-old grandchildren


Let’s start with the youngest grandkids. These are the most fun questions you can ask your grandkids. And you’ll likely get the most unexpected and creative answers.


1) What’s your favorite color and why?

Sure, this one might seem too simple, but it has some legs to it. Knowing your grandchild’s favorite color is a great way to get them talking about things they like — which can spur more ideas and why they prefer them. 


Plus, if you’re looking for gifts for them in the future, you’ll have a good jumping-off point. As an added bonus question, you can even ask them which color they feel like. Take it a step further and look into what their favorite color says about their personality.


2) If you could be any animal, what would you be and why?

Kids at this age are naturally curious and have a vast imagination, and this question allows them to express themselves and their opinions freely. 


Additionally, it can be a fun way to introduce them to new animals while also teaching them about the different traits and characteristics these animals possess. Take it a step further and go into the symbolic meaning of spirit animals.


3) Do you like to make things? What do you like to create?

Making things is one of the best ways for kids to express themselves. It’s also a great way for you to get an insight into their creative interests and talents. Asking questions like this will help your grandkids feel empowered, creative, and supported. 


Plus, it’ll spur some ideas for new projects to work on.


4) What is your favorite thing about playing with your friends?

Like all of us, grandkids love to socialize and make new friends. Asking questions about their friendships will help you get an idea of how they interact with others and if they’re developing healthy relationships. 


Bonus tip: the more you listen, the more you may learn.


5) If you could make a magical potion, what would be in it?

Who doesn’t like magic? Kids certainly do. Use this question to spark their imaginations and get them thinking about all the wild and wonderful things they could do with a magical potion. Getting them to dream big will encourage their natural excitement about achieving.  


6) Which animal is the bravest and why?

This question encourages kids to think about bravery, courage, and what it means to be a hero — all important lessons for them to learn. And their answers may surprise you.


Regardless of their answers, though, this is a great learning opportunity for them to see courage as its core definition, which is “the willingness to act in the face of fear, uncertainty, and doubt.” In other words, the more you try, the braver you become. 


7) What does your best silly face look like?

This one is sure to get some laughs. Not only does it encourage your grandkids to have fun, but it also helps them let loose and express themselves (and you, too).

8) What would you choose if you could eat one thing every day?

Many youngsters have strong opinions about what they like and don’t like to eat, and this question allows them to explore these preferences in a fun and creative way. And it’s also a great way to get them to try new things – or at least open up to the idea of trying new foods.


9) If your pet could talk, what would you talk to them about?

Most kids have (or want) a pet, so questions like this can really get them excited. It’s also an excellent opportunity to explore topics like communication and empathy. 


And if you take into consideration this study on anthropomorphism, what you say to a pet can be pretty telling about the human’s social needs.


10)  If you could make up a game, what would it be called, and how would you play it?

Encourage your grandkid to think creatively and express themselves in a fun way with this question. It also gives them a great chance to practice problem-solving and communication skills. And now you (might) have a new game to play.

11) Do you think it’s better to be big or small, and why?

Asking open-ended questions, can help promote their critical thinking and language development. By encouraging them to express their opinions and thoughts, we can help them develop their communication skills and expand their vocabulary. 


This one also serves as a great learning opportunity – one is not better than the other and different preferences are OK.


12) If you could make any kind of ice cream flavor, what would you make?

Ice cream is a favorite treat for many. Asking questions like this encourages your grandkids to explore their imaginations and think of creative flavor combinations. And who knows, maybe you’ll discover the next best ice cream flavor.


14) What do you think love is?

Love is an important concept for all of us, so questions like this help kids think about its meaning. It’s also a great opportunity to discuss relationships and family values. Sometimes it might just be what you and your grandkids need to hear


And you may get the funniest answers – just check out this video on Cute Kid Answers.


15) What questions would you ask a dinosaur?

Dinosaurs are always an exciting topic for kids, and questions like this help them think about science, history, and the natural world. Use similar questions to open up new avenues for learning and exploring nature. 


With a culture that’s overrun by screens and devices, it’d be remiss not to encourage the enormous mental health benefits of nature.


Questions to Ask Your 5-10-Year-Old Grandchildren

questions to aks your 5-10 year old grandchildren


The older grandkids are, the more questions you can ask them. Here are some questions for 5-10-year-olds that will help encourage their creativity and learning:


16) If you could invent something, what would it be and why?

This question encourages your grandkids’ creativity and helps them explore the possibilities of science and technology. Plus, it’s a great opportunity to discuss inventions and their importance in our lives.


17) What would you do if you had superpowers?

It’s a question we’ve all thought about at some point. But what do your grandkids think would be possible with superpowers? You’ll get some hilarious and fascinating answers. Not to mention, you may stumble across some of the fears they want to overcome. 


For instance, certain superpowers may reveal some shadows you want o overcome. If the insecurities come out, remember to create a safe space where any vulnerabilities are accepted with empathy. 


18) Who is your favorite character from a book or movie, and why?

Books and movies can be great sources of inspiration for kids, so questions like this help them connect with the characters that inspire them. 


It’ll also tell you a lot about their personality and thought process. For instance, you can look into what your favorite move genre says about you. So the character they choose might reflect their own values, interests, or aspirations. 


19) Pretend you’re a chef — what would you make for dinner?

This fun question encourages kids to explore their creativity, think about ingredients and flavors, and create some delicious meal ideas. As an added bonus, you can create the meal together (or perhaps a healthier rendition of it).


20) What questions would you ask an alien if you met one?

This is another great way to get kids’ imaginations going and explore questions about outer space, science fiction, and the unknown. Beyond sci-fi, it’s also a powerful way to think broadly from an objective outside perspective. 


21) What makes you feel proud of yourself?

Questions like this encourage kids to think about their accomplishments and what makes them unique. 


Bonus points if you prompt them to choose a personality trait or something they’re (not) doing. Research shows that focusing on strengths can help kids boost self-confidence and resilience.


22) If you could give money to charity, which one would you choose?

This question helps kids think about those less fortunate than them and encourages them to be charitable. Use it as an opportunity to teach your grandkids about the importance of giving back


After all, giving to others (in a way that feels aligned) is just as good for the giver as the receiver, and naturally makes kids happy.


23) If you could design a treehouse, what would it look like?

Questions like this help kids use their imaginations and explore creative solutions to questions. Plus, who knows — they might even get a treehouse out of the deal if your grandkids’ designs are good enough!

24) What would your perfect day look like?

Start by inspiring them with your perfect day. And encourage your grandkids to dream big — questions like this help them explore the possibilities and come up with ideas that they can strive for. 


25) Who is the kindest person you know, and why?

This is a great way to get your grandkids talking about the people who have impacted their lives in a positive way. According to research, talking about kindness and compassion can help kids develop empathy and social skills.


26) What questions would you ask a superhero if you met one?

Finding out what questions your grandkids have for their favorite superheroes is a great way to get them thinking about values, justice, and heroism. Plus, you’ll learn a lot about their interests in the process.


27) What questions would you ask a time traveler if you met one?

Time travel is always an exciting topic for kids — questions like this help them explore questions about history, time, and the universe. Additionally, it can help them understand concepts such as cause and effect, and the implications of different decisions and actions.


28) What’s the funniest joke you’ve ever heard?

Humor has this unceasing ability to form connections, break barriers, and tickle the hearts of people of all ages. It also encourages play, which is an extremely important learning method for early childhood


Asking a child to share the funniest joke they’ve ever heard not only invites them to delight you with their unique and innocent sense of humor, but also allows for an empowering moment of self-expression. 

29) If you could create a new holiday, what would it be and why?

Kids possess the innate ability to see the world with a certain degree of whimsy and wonder that adults lost somewhere between learning how to file their taxes and begrudgingly making a dentist appointment. 


Asking a child to create a new holiday promises unprecedented ideas – perhaps, a day dedicated entirely to ice cream sundaes, with absolutely no vegetables in sight? Who knows…


30) Who has had the biggest influence on your life so far?

Generally, kids possess an uncanny ability to not only recognize genuine intentions. And it’d be interesting to hear who they think has shaped their lives the most and in what areas.


What’s more, the conversation may spur the topic of mentorship. With 76% of people thinking mentors are important, yet only 37% having one, it’s worth chatting about the value.


Questions to Ask Older Grandkids

questions to ask your older grandkids


Here come the most interesting questions to ask your grandchildren. These questions are targeted for older grandkids and might offer some more serious or thought-provoking answers: 


31) What do you think are the most important values in life? 

It might surprise you, but asking a child about the most important values in life can yield some of the most profound and genuine answers. 


And this heart-to-heart talk can be a gentle reminder for your grandchild to uphold and cherish these core values, ultimately shaping them into their own unique, well-rounded, compassionate individuals. 


31) What’s something you wish you could go back and change in your life?

We’ve all had our fair share of bad decisions or regrest, but learning from them is the vital part. So encourage your grandkids to reflect on their tough experiences and think about the lessons they’ve learned along the way. 


32) What do you think are the most important qualities for success?

By opening up this dialogue, you can create a safe space for your grandkids to express themselves and gain insight into what qualities will help them achieve their vision of success. 


It’s never too early to start thinking about the future, and engaging with your grandkid on this topic can be rewarding for both of you.


33) What are your biggest dreams for the future?

This question is a small gesture that can foster a deep, meaningful connection. Essentially, it shows that you care. And it can turn into a conversation about how they can actually achieve those dreams. 


Bonus tip: if their dreams appear practical (or too reminiscent of someone else’s dreams), encourage them to dream bigger. Digging into layers of “why” their dreams are important helps deepen the intrinsic motivation, too.


34) In what ways have you seen yourself grow and change over the years?

It’s an opportunity for them to reflect on their experience and share moments of growth which can be both inspiring to hear and serve as teachable moments. Plus, you might even learn a thing or two.

35) What advice would you give your younger self? 

Have you ever heard the saying “with age comes wisdom”? And that doesn’t necessarily have to mean old age. Asking your grandkids this question could open up an interesting conversation about their personal growth.


36) If you could pick one cause to fight for, what would it be and why?

Get your grandkids thinking about social justice, morality, and their passions and purpose. This is a great way to open up discussions about the power of standing up for what’s important. 


35) What would you tell the world if you had a platform to reach everyone?

Allowing them to express themselves and be heard could lead to some truly inspiring and impactful ideas. They have a fresh perspective, a new take on what’s important, and they’re not afraid to speak up about it. 


36) What’s one thing you wish adults understood about being a teenager?

Let’s face it, the teenage years can be tough for everyone involved. But sometimes, as adults, we forget what it’s like to be in that complicated stage of life. By asking your grandkid this question, you could gain some valuable insight into their world. 


37) What’s the most inspiring thing you’ve seen or experienced recently?

Kids these days are exposed to so much – from social media to news stories from around the world – and it can be easy to overlook just how much they’re taking in. 


By asking them what’s been inspiring them lately, you might just be surprised by the breadth and depth of their curiosity and creativity. 


38) Who would you say is your biggest supporter? Why?

It’s a question that taps into their self-awareness, as well as their perception of the people around them. Highlight how important it is for them to feel supported.  


With poor social support being linked to risks like alcohol use and depression, every kid needs someone to root for them and believe in their dreams.


39) If you could speak with anyone from history, who would it be, and what would you ask them?

It opens up a window to their interests, curiosities, and knowledge about history. And it’s an opportunity for them to express their curiosity and explore questions of legacy and heritage. 


40) If you had one day with no responsibilities or obligations, how would you spend your time?

It’s always refreshing to think about the potential of what could be accomplished in 24 hours without any interference. Asking your grandkid this question not only helps you get to know them better, but it can also spark interesting conversations and ideas. 


Who knows, maybe their response will inspire you to take a day off for yourself and indulge in some guilt-free relaxation.


41) What’s something you’ve always wanted to learn but haven’t had the chance to yet?

Have you always wanted to learn something new, but never had the chance? Well, why not ask your grandkids? They are full of curiosity and have an enthusiasm for learning that is contagious. 


You might be surprised to find out what they want to learn, and who knows, maybe you can even learn something new together. It’s never too late to try new things and broaden your horizons; involving your grandkids in the process can create memories that will last a lifetime.

42) What are your thoughts on adversity? How have you faced difficult situations in the past? 

Questions like this help older grandkids reflect on questions of resilience and grit. Give them a chance to share their stories and explore questions of courage and perseverance. 

43) What would you say is the most important lesson you’ve learned so far in life?

Sure, they may be young, but the experiences and challenges they’ve faced can reveal a lot about who they are and how they view the world around them. 


Plus, it’s always a great opportunity to connect with your grandkid on a deeper level and learn more about what makes them tick. This is also a great way to set the tone for a future dynamic that’s open for deeper topics.

44) What’s the coolest thing you’ve ever made or created?

This is a great question to ask throughout the years, as the answers should mature, too. They might surprise you with something that you never expected, whether it’s a drawing, a fort they built, or even a recipe they invented in the kitchen. 


Get a glimpse into their creativity and even inspire them to continue exploring their innate interests more deeply. With 75% of people not living up to their creative potential, it’s worth the friendly nudge to dive deeper. 


45) If you could go back in time and fix one mistake, what would it be?

This one also never gets old. Learning about their past decisions and how they would handle them differently can provide a fascinating insight into their unique views on life and important learnings. It can be even more engaging if you share your do-overs and how they changed you.


46) If you could live in any time period, which one would you choose and why?

Some might choose the roaring 20s for the fashion and jazz music, while others might choose the 1960s for the civil rights movement and counterculture. Whatever their answer may be, it’s sure to spark some lively discussion and insight into their authentic values.


47) What would you say is the best advice someone has ever given you? 

There’s always room to learn more about life – at every age. And who better to learn from than your very own grandchildren? Asking them what the best advice they’ve ever received is not only a great conversation starter, but it can also be a valuable learning opportunity for you. 


Of course, if the opportunity arises, it’s nice to share your wisdom, too. Not to mention, it’s also a great time for you to do your own self-reflection. And if you need inspiration, look to these quotes by famous people.


48) What questions would you like to ask yourself in five years?

This is a great way to get kids thinking about questions of growth and progress. It encourages them to think about their ideal self and express their hopess – a powerful way to explore questions of aspiration and development. 


49) What would you do if you had an extra hour in the day?

We’ve all wished for that at one point (or several times daily). And kids these days have so many activities and obligations filling up their schedules, they often don’t have time to dream or ponder what they would do if given just a bit more time. 


Bonus tip: If the answer hints at relieving stress with their time (i.e. finishing homework, relaxing in-between extra curricular activities, etc.), add the caveat, “if you had all your responsibilities taken care of and you had all the energy for it…”


50) What do you want to be remembered for when you’re gone? 

Questions like this help older grandkids reflect on questions of legacy and impact. Which can, of course, give their career paths more meaning and depth. Consider it as an opportunity to exchange values and find more urpose and meaning


51) If you could switch lives with anyone for a day, who would it be and why?

Imagine having the chance to walk in someone else’s shoes for a day. Who would you choose? 


If you ask your grandkid, their answer may surprise you. Maybe they’d want to switch lives with a superhero like Spiderman, or perhaps they’d prefer to see what it’s like being a world-renowned chef. Either way, it’ll give some good insight into what intrinsically motivates them.

52) What’s the most important lesson you’ve learned so far in your life?

Again, this is an important self-reflection question to be asked at all life stages. It’s an opportunity for them to practice reflecting on their own personal growth and understanding where they want to go (and how to get there). 


Plus, your grandkids are growing up in a world that’s vastly different from the one you grew up in, so taking the time to listen to their perspectives and experiences can be eye-opening.


53) What’s something you’re embarrassed to admit you like, but secretly enjoy?

This one might be a stretch, but by sharing your own experience of something you secretly enjoy, you may be able to create a more comfortable space for them to open up about their guilty pleasures. 


After all, a whopping 84% of us have guilty pleasures, so at the very least, it’s an opportunity to get to know them better and maybe even discover some common interests. 


54) If you had to pick just one song to listen to for the rest of your life, which one would it be?

Asking your grandkid which one song they would choose to listen to for the rest of their life might seem like just a fun little game at first. But if you really think about it, there’s so much that could be learned from their answer. 


Their choice could say a lot about their personality, their style, and what moves them emotionally. Plus, who knows? Maybe they’ll introduce you to a song or artist you’ve never heard before, and it could become your new all-time favorite, too. 


Extra Questions to Ask Your Grandchildren

Extra questions to ask your grandchildren


And finally, here are a couple of bonus questions to ask your grandchildren: 


55) What would you say if you could write a letter to yourself in 5 years? 

Kids have a way of seeing things that adults may overlook or dismiss. And they’re not as likely to be afraid to dream big or consider the possibilities. And you could even write an email to yourselves using FutureMe. Just imagine how cool it’ll be to read them in a few years.

56) What would you do if you could change one thing about yourself?

As you age, sometimes you become set in your ways and forget that there is always room for lifelong learning, growth, and improvement. 


Asking your grandkid for their thoughts on the matter could spark a growth mindset and lead to some important self-refelction and self-discovery that’s necessary for their current and next life phase. 


57) If you could go anywhere, where would you go?

Traveling is a fantastic way to learn about new cultures, broaden your perspectives, try out new foods, and create memories that last a lifetime. So, why not ask your grandkid where they would go if they could travel to any place in the world? 


It can be a conversation that opens a world of opportunities for the two of you to bond and share experiences.


58) If you could change one thing about the world, what would it be?  

This is a great question to get your grandkids thinking outside of themselves and into bigger issues in the world around them. Encourage them to express how they would make the world a better place. 


And it’s an excellent opportunity for you to share your own experiences and beliefs, encouraging them to create a better world for future generations. 


59) What is something you have learned that you are proud of?

As adults, we often find ourselves giving advice and sharing our own life experiences with our kids. But have you ever considered flipping the script and asking your grandchild what they have learned that they’re proud of? 


Encouraging them to share how they’ve improved builds confidence.


60) Can you teach me something?

Along the same vein, this question is a great way to foster a stimulating learning environment for your grandchild. It’s also an opportunity to gain insight into their interests and passions, which can help you better connect with them. 


Turn the Tables

Turn the tables and let them ask the questions. 


Not only does it put your grandkid in the driver’s seat, but it also encourages them to think about values that are important to them.


These questions are a great way to bridge the gap between generations, inspire meaningful conversations, and get to know your grandkids better.


And these questions are just the beginning — with a little bit of creativity, you can come up with many more fun questions, activities, and projects to share with your grandkids!


So have some fun with it — you never know what kind of interesting momentum will come of it.

What's Your Retirement Purpose?

These 10 questions can make all the difference
portrait of Cyn Meyer, founder of Second Wind Movement and a certified retirement life coach
Cyn Meyer 

Retirement Life Coach

As a certified retirement life coach since 2018, Cyn has helped thousands of older adults turn their retirement years into remarkable years full of growth, purpose, and passion. Through her signature program Rewire My Retirement, she helps people achieve their best life across the 5 Rings of Retirement, which covers topics Growth, Community, Health, Giving Back, and Finance.

Cyn combines specific life coaching tools, neuroscience, and her extensive background in marketing (spanning 17 years) to make a powerful impact with Second Wind Movement – an organization dedicated to providing educational resources and coaching for seniors.

With meticulous research, insight, and passion, Cyn’s mission is to usher in a new wave of positive experiences for generations of retirees.

portrait of Cyn Meyer, founder of Second Wind Movement and a certified retirement life coach

Cyn Meyer 

Retirement Life Coach

As a certified retirement life coach since 2018, Cyn has helped thousands of older adults turn their retirement years into remarkable years full of growth, purpose, and passion (beyond the stereotypical financial planning side of retirement). 

She combines specific life coaching tools, neuroscience, and her extensive background in marketing (spanning 17 years) to make a powerful impact with Second Wind Movement – an organization dedicated to providing educational resources and coaching for seniors.

With meticulous research, insight, and passion, Cyn’s mission is to usher in a new wave of positive experiences for generations of retirees.