You’ve asked your grandkids a million questions over the years (and isn’t that half the fun?). Now it’s their turn! Let them guess and giggle as they try to answer questions about you. Don’t worry—you don’t have to bring up the time you accidentally sent your love note to the wrong person in high school!
Instead, these are sweet little questions about your favorite things, memories, and dreams. So if you’re ready to open up that old memory box, here are 50 age-friendly questions to get the fun started!
For Toddlers (2-4 years old)
Can you guess what grandma’s favorite animal was when she was your age?
Can you guess what kind of food Grandma loves the most?
Do you know what Grandma’s favorite color is?
Do you know what Grandma’s favorite game was?
Do you know what Grandma’s favorite holiday is?
Do you know what Grandma’s favorite movie is?
Do you know what Grandma’s job used to be?
Do you know where Grandma used to live when she was little?
What kind of games do you think Grandma used to play as a little girl?
What kind of toy do you think Grandma liked to play with?
For Pre-Schoolers (5-6 years old)
Can you guess Grandma’s favorite book when she was your age?
Can you guess Grandma’s favorite childhood movie or TV show?
Can you guess what Grandma’s favorite childhood memory is?
Do you know Grandma’s favorite season of the year?
Do you know what makes Grandma laugh the most?
Do you know where Grandma was born?
What do you think Grandma wanted to be when she grew up?
What do you think was Grandma’s favorite vacation she ever took?
What kind of music do you think Grandma liked to dance to when she was your age?
What type of food do you think Grandma loved most as a child?
For Elementary School Kids (7-10 years old)
Can you guess what Grandma’s favorite ice cream flavor is?
Can you guess what Grandma’s favorite thing to cook or bake is?
Can you guess where Grandma would love to travel if she could go anywhere in the world?
Can you guess which sports or hobbies Grandma was into?
Do you know how Grandma and Grandpa met?
Do you know what Grandma had for her first pet?
Do you know what subjects Grandma liked best in school?
What do you think Grandma used to do in the summer?
What do you think that (pet) was named?
What kind of chores do you think Grandma had when she was your age?
For Middle School Kids (11-13 years old)
Can you guess Grandma’s favorite hobby?
Can you guess Grandma’s first job and what she bought with her first paycheck?
Can you guess what fashion trends Grandma followed when she was your age?
Can you guess what the coolest piece of technology was when Grandma was your age?
Can you guess what was Grandma’s first car?
Can you guess who Grandma’s childhood hero was?
Do you know what Grandma’s favorite song is?
Do you know who was Grandma’s first best friend?
What was Grandma’s favorite book or book series in middle school?
What were Grandma’s favorite band and type of music in middle school?
For High School Teens (14-18 years old)
Can you guess what car Grandma drove or wanted to drive in high school?
Can you guess what Grandma’s favorite family tradition is?
Can you guess what prom or homecoming was like for Grandma?
Can you guess what was the first concert Grandma ever attended?
Do you know what Grandma considers to be her greatest accomplishment?
Do you know what Grandma studied in college or what she wanted to study?
Do you know what Grandma’s dream was when she was in high school?
Do you know what historical event had the biggest impact on Grandma when she was young?
Do you know who Grandma’s best friend was in high school and a fun adventure we had together?
What kind of clubs or sports was Grandma involved in during high school?
Conclusion
The real goal of these questions is to help you and your grandchild have fun together while sharing little pieces of your own story. It’s not a test—it’s a chance to laugh, learn, and connect. So take your time, enjoy every answer, and let the conversation flow.
And if you haven’t yet, be sure to check out my other sets of questions for grandkids—you’ll find even more ways to spark sweet memories and giggles together. ❤️
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