Have you ever noticed how your grandkids look at you like you’ve always been a grown-up? They can’t quite imagine you climbing trees, scraping your knees, or giggling past curfew.
That’s why these fun questions are such a treat — they open the door to stories that show you were once a curious, silly, and mischievous kid too!
Get ready for laughter, surprise, and a few “No way, Grandma!” moments that will bring your generations even closer.
Can you guess what my favorite food was when I was little?
How about what I loved to do for fun when I was your age?
Do you think you could guess what I liked to wear back then?
Can you guess what I dreamed of becoming when I grew up?
What do you think made me laugh the most as a kid?
Can you imagine what my biggest dream was when I was your age?
Do you know what my favorite playground game was?
Can you guess what I felt most proud of as a child?
Do you know what kind of car I drove first?
What kind of student do you think I was in school?
Can you guess what my favorite subject was—and why?
Do you know what my very first concert was?
What do you think was the most important lesson my parents taught me?
Do you know how my parents punished me when I misbehaved?
Can you guess how old I was when I had my very first crush?
What do you think my favorite TV show was when I was your age?
Do you know what I saved up for and bought with my own money?
Can you guess what my first job was?
Where do you think my family liked to go on vacation?
How do you think I celebrated my birthdays growing up?
Do you know how I met my first boyfriend (or girlfriend)?
How do you think we celebrated Halloween back then?
Can you imagine how I did my homework before we had the internet?
Do you know how I met your grandpa?
What do you think I loved doing most during summer break?
How do you think I spent my weekends as a teenager?
Do you think my life was very different from yours at your age?
What kinds of things do you think I did with my friends?
Can you guess what I liked doing on Saturday mornings?
What dreams do you think I had as a young adult?
Can you guess what my favorite toys were when I was little?
What kind of music do you think I listened to as a teen?
What were family celebrations like when I was young?
Can you guess what chores I had to do around the house?
Do you know what hobbies I loved most?
Can you guess what book I loved as a child—and why?
What was my favorite family vacation and why?
What was my favorite holiday tradition when I was little?
Can you guess what movie I watched over and over again as a kid?
What do you think my most treasured childhood possession was?
What was the most popular fashion trend when I was your age?
Can you guess which chores I liked and which ones I didn’t?
What were the best and worst parts of school for me?
Who was my very best friend—and why were we so close?
Who do you think was my role model when I was your age
The best part about asking these questions isn’t just the laughter — it’s the connection. When your grandkids see that you once had favorite games, goofy moments, and big dreams just like they do, something magical happens: they start to see you as both wise and wonderfully human.
So go ahead, keep the conversation going, share a few stories, and let them know that growing up doesn’t mean losing your sense of fun — it just means you have more stories to tell.
Read Also: These 50 Questions Will Make Your Grandkids Finally See the Real You
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