One thing is clear: it’s not always easy to connect with different generations. That’s been true for a very long time. Sometimes, you might not know what to say or ask your grandkids. I’ve had plenty of quiet moments with mine—especially now that they’re older and busy with so many things.
That’s why I created these 80 conversation starters. They’re written in a fun Fill-in-the-Blank style. You can take turns asking each other questions, or just use them however you like. There are no rules! I hope these prompts help you and your grandchildren learn more about each other and grow even closer.
P.S. You can download a printable version at the end of the article!
Conversation Starters for Grandchildren to Answer
The first 40 questions are made for your grandchild to read and fill in the blanks. If they can’t read yet, you can read the questions out loud and help them answer.
As you go through the questions, see what fun stories or follow-up questions come up. These prompts are meant to help you connect and learn more about your wonderful grandchildren.
Fun and Silly Questions
1. If you could be any animal for a day, what would you be and why?
2. What would your dream treehouse look like?
3. If you opened a restaurant, what food would you serve?
4. What’s the weirdest food you’ve ever eaten—or want to try?
5. If you had a superpower, what would it be and what would you do with it?
6. What would you name your own planet?
7. If your pet could talk, what do you think it would say?
8. What’s something that always makes you laugh, no matter what?
9. If you could invent a new holiday, what would it be for?
10. What would your superhero costume look like?
Storytelling and Imagination
11. Can you tell me about the best dream you ever had?
12. If you could visit any time in history, where would you go?
13. What would you do if you found a secret door in your backyard?
14. What kind of book would you write if you were an author?
15. If your life were a movie, what would the title be?
Feelings and Values
16. What makes you feel brave?
17. What’s something kind someone has done for you?
18. What does being a good friend mean to you?
19. What’s something you’re really proud of?
20. When do you feel the most loved?
Learning and Growth
21. What’s something new you’ve learned lately?
22. If you could learn anything in the world, what would it be?
23. What’s the hardest thing you’ve ever done—and how did you do it?
24. What do you do when something feels too hard?
25. What’s something you want to get better at?
Family and Memories
26. What’s your favorite memory with me?
27. What’s something funny our family does?
28. Do you know how your parents met?
29. What’s your favorite family tradition?
30. What’s the best trip you’ve ever been on?
Modern Life and Interests
31. What’s your favorite thing to do on the weekend?
32. If you could create your own video game, what would it be like?
33. Who’s your favorite YouTuber or TV character—and why?
34. If you could redesign your room, what would it look like?
35. What’s an app you wish existed?
Big Ideas and Dreams
36. What kind of job do you think you’d love someday?
37. If you were president for a day, what would you change?
38. What’s one thing you wish everyone in the world knew?
39. If you had a million dollars, what would you do with it?
40. What kind of person do you hope to be when you grow up?
Conversation Starters for Grandparents to Answer
Now it’s your turn to share! Don’t worry if your grandkids don’t seem as excited to hear your answers as you are to hear theirs. That’s totally normal. 🙂
Keep things light and fun. You can even turn the question around and ask, “What about you?” I hope these questions help you remember special memories—and maybe even teach your grandchildren something new along the way.
1. My favorite toy when I was a child was ____________.
2. The pets I had when I was growing up were named ____________.
3. My favorite subject in school was ____________.
4. The first job I ever had was ____________.
5. My best friend when I was little was ____________.
6. One of my favorite childhood games was ____________.
7. I used to love listening to ____________ on the radio.
8. My favorite meal my mom or dad made was ____________.
9. My first car was a ____________.
10. The chore I liked the least growing up was ____________.
11. One of my funniest memories from school is ____________.
12. My favorite book when I was young was ____________.
13. My family celebrated holidays by ____________.
14. When I was your age, I wanted to grow up to be ____________.
15. The first time I went to the movies, I saw ____________.
16. A fashion trend I used to follow was ____________.
17. My favorite candy or treat as a kid was ____________.
18. My grandparents used to ____________ with me.
19. I remember when ____________ first became popular.
20. One thing we didn’t have when I was young was ____________.
21. The neighborhood I grew up in was ____________.
22. My favorite season when I was a kid was ____________ because ____________.
23. I got in trouble once for ____________.
24. We used to travel by ____________ when going on trips.
25. My favorite place to visit as a child was ____________.
26. My school looked like ____________.
27. We used to watch ____________ on television.
28. The most exciting thing I did as a teenager was ____________.
29. My favorite outfit I wore growing up was ____________.
30. One thing that’s very different today is ____________.
31. When I met your grandma/grandpa, we were ____________.
32. Our first date was ____________.
33. My wedding day was ____________.
34. One of my proudest moments in life was ____________.
35. I used to love dancing to ____________.
36. The most valuable lesson I learned as a young adult was ____________.
37. One thing I hope you always remember is ____________.
38. I always wanted to try ____________, but never did.
39. The advice I would give my younger self is ____________.
40. Being your grandparent makes me feel ____________.
Print the PDF Version
If you want a clean copy of all 80 conversation starters—without any annoying ads—you can download the PDF here:
Click here to get your free copy!
Here’s to great conversations, learning more about each other, and feeling closer than ever. I hope you enjoy!
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