60 More Questions to Spark Connection and Giggles With Your Grandkids

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If you get my newsletter, then you already know how much I love asking my grandkids silly, sweet, and thoughtful questions—it’s one of my favorite ways to connect with them! Did you catch my first list with 20 fun questions, 20 “Would You Rather?” games, and 20 “This or That?” choices?

Well, good news! So many of you asked for more, and now I’ve added 20 extra of each—for a total of 60 screen-free ways to laugh, chat, and make memories with your grandkids.

Questions to spark connection, giggles, and deeper conversations with your grandkids

1. What’s the funniest thing you’ve ever seen or heard?

2. If you had a pet dinosaur, what would you name it?

3. What’s something you wish grown-ups understood better about kids?

4. If you could trade places with any character in a book or movie, who would it be?

5. What superpower do you think would be the most fun to have?

6. What do you think clouds feel like?

7. If you could make your own school, what would it be like?

8. What’s one thing you want to learn how to do this year?

9. If you could time travel, what time would you visit and why?

10. What’s something you’ve done that made you feel really proud?

11. If you were a chef, what would your restaurant serve?

12. What do you think makes someone a good friend?

13. What’s your favorite memory with your family?

14. If you had your own theme park, what would it be called?

15. What kind of animal would you be if you could choose?

16. What’s one thing that always makes you smile, no matter what?

17. If you could give your stuffed animals real voices, what would they say?

18. What would you put in a time capsule to show people in the future what life is like today?

19. If you had a magic backpack, what would always be inside it?

20. What do you think love feels like?

Imaginative “would you rather” questions to ask your grandkids

1. Would you rather have a robot for a best friend or a dragon?

2. Would you rather slide down a rainbow or jump on clouds?

3. Would you rather have spaghetti for hair or marshmallows for toes?

4. Would you rather live in a giant candy store or a zoo?

5. Would you rather only be able to whisper or only be able to shout?

6. Would you rather have a talking dog or a flying cat?

7. Would you rather build the tallest LEGO tower or the biggest blanket fort?

8. Would you rather have a birthday every day or Christmas every week?

9. Would you rather have glow-in-the-dark skin or hair that changes color?

10. Would you rather race a cheetah or wrestle a bear (gently!)?

11. Would you rather be a famous chef or a famous inventor?

12. Would you rather live underwater or on the moon?

13. Would you rather find a hidden treasure or a secret map?

14. Would you rather have fingers made of jelly or feet made of popcorn?

15. Would you rather spend the day with a pirate or a wizard?

16. Would you rather make your bed with whipped cream or sleep in a sleeping bag made of leaves?

17. Would you rather go on a jungle safari or a deep-sea submarine trip?

18. Would you rather have a snowball fight in summer or a water balloon fight in winter?

19. Would you rather make friends with a unicorn or a T-Rex?

20. Would you rather be able to talk to animals or control the weather?

Creative “this or that” questions to ask your grandkids

1. Summer or winter?

2. Dinosaurs or dragons?

3. Pizza or burgers?

4. Superhero costume or princess dress?

5. Camp in a tent or stay in a cabin?

6. Ride a scooter or a skateboard?

7. Play board games or video games?

8. Go to the zoo or the aquarium?

9. Paint with your fingers or use a brush?

10. Eat breakfast for dinner or dinner for breakfast?

11. Climb a tree or splash in puddles?

12. Wear pajamas all day or dress up fancy?

13. Make a snow angel or catch snowflakes on your tongue?

14. Be really silly or super serious?

15. Watch cartoons or read comics?

16. Have rainbow hair or glittery skin?

17. Go on a treasure hunt or solve a mystery?

18. Visit the farm or the city?

19. Eat popcorn with butter or with cheese?

20. Share your toys or trade them?

I really hope you have as much fun with these extra questions as my grandkids and I have! I’d love to hear how it goes—feel free to send me an email or leave a little note on Facebook. Let’s chat again soon, okay?

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