Finding Joy in AI, One Riddle at a Time
How a simple AI experiment turned car rides into laughter, pages into creativity, and technology into family connection.
My nearly-eight-year-old is in her riddle phase. You probably know it:
“What’s brown and sticky?”
“A stick.”
It’s cute the first time. The twentieth time? Not so much. That’s when I realized we could bring AI into the mix — not as a distraction, but as a way to spark more laughter together.
A Car Ride Becomes a Riddle Factory
One afternoon in the car, I suggested: “Why don’t we ask ChatGPT for some riddles?”
She agreed — but only if I didn’t see them first. So I typed: “Give me a list of 20 riddles appropriate for a 7-year-old.” And then closed my eyes and handed her my phone.
She read each one and had us all laughing. We had escaped the endless loop.
Riddles on ChatGPT
From Digital to Tangible
Soon she wanted more: “I want my own riddle book.”
With AI, that wasn’t just possible — it was easy. Together we asked ChatGPT to:
Gather 100 simple riddles and 100 harder ones
Leave blank pages for her own creations
Add a doodle-style cover for decorating
ChatGPT formatting the PDF
It took a few tweaks to get the formatting and design correct but within 30 minutes, we had a real book in hand.
The printed version
Family Craft Time (Staple Guns Included)
What happened next was even better than I expected. She sat down with markers and stickers, turning the blank cover into a masterpiece. She flipped through the pages, testing out riddles on us, circling her favorites, and even inventing new ones in the blank sections.
It wasn’t just about riddles anymore — it was about ownership, about making something together.
The only snag? Binding. Our stapler was broken. No problem: her dad, never one to be defeated by a household mishap, grabbed a 2x4 and a construction staple gun. He stapled the pages into the wood, pulled the booklet free, and flattened the staples with pliers. Suddenly, her homemade riddle book looked and felt like the real deal.
The finished product!
Why This Matters
On the surface, this was just a weekend project. But it showed me how AI can be a joy enabler for families:
Turning repetition into fresh fun
Making something personalized and tangible
Letting my daughter be a creator, not just a consumer
Bringing us together around shared laughter
And it cost nothing but imagination.
Takeaway
For free, we created a custom riddle book that turned screen time into more reading, more creativity, and more joy.
This is what excites me about AI at home: not replacing our connections, but amplifying them. With intention, AI can transform the ordinary — like car rides and riddles — into memory-making experiences.
At Hold My Juice, we’re building technology that brings joy back to family life by creating space for what matters most. This post is part of a series exploring how you can use AI in everyday family moments — turning routines and even chaos into opportunities for laughter, creativity, and connection.
