5 Key Questions to Get to Know Your Grandkids
5 Key Questions to Get to Know Your Grandkids
By Allen Wolf, Game Creator and Filmmaker
Babyboomers.com Staff

When I was in high school, my grandmother lived with our family in our basement guest room. She enjoyed a comfortable bed, a piano we often begged her to play, a bathroom, and everything else she needed. Except for frequent company. Both my parents and my sister were at school all day. So whenever we returned and we stopped by to say hello after school, her face lit up, and she would ask us about our day. Being teenagers, we didn’t have a lot to say. “It was fine,” was usually our standard answer. Then, after we asked her how she was doing, the conversation would soon ground to a halt, and we would scramble back to our room until she joined us for dinner.

When I look back on the time my grandma lived with our family, I can see that she wanted to connect with my sister and me, but she didn’t know how to engage us in conversations. I created my You’re Pulling My Leg! game to make that kind of connection. It’s helped me grow closer to my wife, our neighbors, and our family, and it will do wonders in helping you connect with your grandkids.

Typically, if you ask grandkids about their day, the conversation can quickly dry up. With younger kids, if you ask direct questions, they might feel shy about answering. But in the context of a game, people love talking about their lives, and they get a kick out of crafting their stories.

Here are five questions from You’re Pulling My Leg! and You’re Pulling My Leg! Junior that will help you connect to your grandkids in meaningful ways:

Tell me about a time when you did something you didn’t think you’d do.

Your grandkids might want to tell you about something they did that was courageous or daring, and this question gives them that chance. Or perhaps they’ve done something they regret. This question allows them the opportunity to open up to you. This moment is also an opportunity for you to be vulnerable as well. You’ll quickly discover that your willingness to open up about your life will encourage your grandkids to do the same.

Tell me about someone you would switch places with if you could.

This question gives you a window into how your grandkids perceive themselves and their circumstances. Do they long to live a different kind of life? Explore other opportunities? Be someone else? You can also answer this question and give your grandkids a deeper sense of your dreams and passions.

Tell me about a time when you worried about your parent(s).

You might discover that your grandchild carries more burdens than you imagined. This question gives you the chance to speak into whatever issues or concerns your grandkids might be experiencing. 

Tell me about a time when you were nervous about meeting someone.

This question will help you figure out if your grandchild is romantically interested in someone or felt anxious about a job interview. Either way, it gives you a glimpse in a situation that jangled their nerves, and it’s a chance for you to share how you have felt in similar situations.

Tell me about something adventurous you did with a friend.

Your grandkids might have some exciting stories to tell, or this might help them realize they spend too much time on their phone and need to embark on more adventures. You could give them the nudge they need and join them in discovering something new.

You’re Pulling My Leg! is for ages thirteen and up, and You’re Pulling My Leg Junior is for ages nine and up. These games feature all these questions mixed in with many others throughout the game, and players get to choose which three questions they’d like to answer. You’ll be surprised at how much your grandchildren will open up within this game’s context, and you’ll have a lot of laughs and moments of wow as you share about each other’s lives. See more at morningstargames.com.


Allen Wolf is an award-winning game creator, author, and filmmaker. He has created five games that have won 39 awards. He is also the author of the novel Hooked that has been adapted into a movie that will be released in 2021. Allen’s first film is the Hitchcockian thriller In My Sleep which is available on Blu-ray or to stream on Amazon Prime. See more about the game creator at www.allenwolf.com. 


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