The Sweetest Mama-Son Date (And the Questions That Made It Magic)
Lately, I’ve felt a quiet ache—something familiar to many mamas. The feeling that one child is getting most of my time while another might be needing more of me.
As of writing this, I have two boys—one is six, and the other is about 15 months. My youngest still breastfeeds, so he’s naturally with me most of the time. But with my oldest, Diego, I started noticing the distance. I missed him. I missed us. So I decided it was time for a date—just the two of us.
Planning With Intention
I wanted it to be more than just an outing. I wanted it to be something we’d both remember. So I told my husband what I had in mind (he was all for it) and gave myself a few days to plan something special. I didn’t want to default to a movie or a playground. Those are fun, of course, but they don’t always give us the chance to truly connect. I wanted something where Diego and I could interact—face to face, heart to heart.
We ended up choosing a paint splatter room—just imagine us in ponchos and booties, blasting paint at canvases with water guns under blacklights! It was loud, colorful, messy, and so much fun. Afterwards, we went out to dinner at Tycoon Flats and ended the night with ice cream at Black & White Modern Creamery.
Enter: The Magic of 50 Questions
During dinner, Diego spotted a play area and excitedly ran off. It was sweet to see him so happy, but I really wanted some talking time—a way to dive into his thoughts and imagination. That’s when I asked ChatGPT to help me come up with 30 fun questions to ask a six-year-old. I started asking him while we ate, and right away, it was like a window opened into his heart.
We laughed, imagined, got silly, and got tender. He gave me answers that surprised me, like when I asked him what love feels like, and he said:
“Like a million hugs all at once.”
Cue my melted mama heart.
He enjoyed the questions so much that he asked me to come up with 20 more. So we did that over ice cream. It turned out to be one of the most special, connection-rich moments we’ve had in a long time.
Why It Mattered
These simple questions made it easier to connect. Sometimes, I sit down with Diego and feel unsure of what to ask or how to get more than a few words in response. But this gave us a shared rhythm, a fun back-and-forth that deepened our conversation and made dinner feel like a game.
It reminded me that I don’t need anything elaborate to reconnect with my child—just presence, a little planning, and the right questions.
To the Mamas Who Are Tired, Busy, or Feeling Disconnected
I know how full your days are. I know how quickly time gets away from us. But I also know that the connection you long for with your child is just a moment away—waiting to be rekindled.
My encouragement? Make a plan. Put a date with your child on the calendar. Even if it’s two weeks from now. Even if it’s just for an hour. Sometimes, creating a memory together is more nourishing than checking off one more thing on the to-do list. You deserve that joy, and so does your child.
Want to Try It?
I’ve put together the full list of 50 questions I used with Diego in a printable PDF so you can use them too—at dinner, on a walk, during a car ride, or while cuddled up at bedtime.
You can head to the Resources tab, click Free Downloads and then select the Big List of Little Kid Questions link OR click the link down below.
The Big List of Little Kid Questions
I hope this inspires you to slow down, take a breath, and reconnect with the little person who loves you most.
And if you think I should create a list of older kiddos send me an Instagram DM or let me know in the comments!