50 Eye-Opening Questions To Ask Your Grandchildren

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02-07-2025

There's something special about the connection between a grandparent and a grandchild. While this bond goes deeper than words, conversation is a great way to get to know your grandkid and help keep that connection strong.
But getting a conversation started, or keeping one going, isn't always easy. Maybe your grandchild is on the shy side, you haven't seen one another in a while or you're connecting on a video call instead of in person.
A juicy question — the kind that leads them to see something in a new light, or inspires them to tell a story — can get a conversation started, or get it rolling again if you hit a lull.
'The point of asking questions should be to get to know your grandchildren better,' DeeDee Moore, a grandmother who blogs at More Than Grand, told HuffPost.
Asking kids to elaborate with follow-up questions and open-ended prompts like 'What makes you say that?' are also a good way to keep kids talking.
'If you ask what their favorite color is, ask why they like it or how that color makes them feel,' Moore suggested.
Part of the joy of asking kids questions is the surprise that their answers may bring, leading your conversation to take an unexpected turn.
'When I asked my four-year-old granddaughter if she had talked to any of her friends at school today, she initially said no,' Moore recounted. 'But then she explained, 'I just meowed because I was a kitty.' Instead of finding out more about her school day, we ended up having a conversation about how animals talk.'
Here are some questions you can use to start a conversation with a grandkid or to keep one going.
What's something you're really good at? 'A great follow up is to ask them to teach you how to do it,' Moore added.
If you could invite anyone in the whole world to dinner, who would you invite?
If you could walk into any book or movie, which one would you choose?
If you could be any animal, which one would you be?
Would you rather be able to fly like a bird or swim like a fish?
If you were a superhero, what would your superpower be?
Would you rather be able to tell the future or read other people's minds?
What was the last thing that happened that made you laugh?
What is something kind that someone has done for you?
What is something about you that I don't already know?
What do you think you'll be doing ten years from now?
Where in the world would you most like to visit?
Would you rather travel back to the past or into the future?
What is something you want to learn how to do?
What is your favorite thing about yourself?
Would you rather travel underwater or in outer space?
If your toy could talk, what would it say?
What is your favorite time of the year?
What is something about you that is unique?
What kind of mom or dad do you think you would be?
What do you think your pet is thinking right now?
What would you do with a thousand dollars?
What would you like to be famous for?
What makes somebody a good friend?
Would you rather be tiny like an insect or as tall as a giraffe?
What do you think is the best smell on earth?
What was the last dream that you remember?
When you get bored in school, what do you start thinking about?
Would you rather be the star of a movie, or the director?
What is a job that you wouldn't want to do?
Do you think it's ever a good idea to tell a lie?
How do you show someone that you love them?
What was your favorite part of the day?
Who is your favorite person right now?
Would you want to live forever?
What would a perfect day look like for you?
Would you rather have a pet dragon or a pet unicorn?
If you could have any kind of store, what would you want to sell?
What is the silliest thing you've ever done?
What do you think is the most important rule for people to follow?
Would you rather dance or paint what you are feeling?
If you had to eat the same thing for every meal, what food would you choose?
What is the weirdest thing you've ever tasted?
How can you tell if somebody is smart?
What is something brave that you have done?
If you wrote a book, what would the title be?
If you could change one thing about the world, what would it be?
What is something that used to scare you but doesn't anymore?
How do you think the world will be different by the time you are a grown up?
What is something you've done that you would like to do again?
More important that the question that gets them talking is how well you listen once you get them started.
'Listening carefully to your grandchildren is the greatest gift you can give them,' Moore said. Remembering details like their friends' names shows that you're paying attention and that you care.
'It builds a true connection when you show that you are interested in their lives.'
And while there are advantages to having a conversation face-to-face, like being able to read someone's body language or decipher their tone, you don't have to be physically present with your grandchild to make a connection.
Moore explained: 'Showing a curiosity for who they are can be done just as easily over video chat or in a letter as it can be over ice cream.'