Halloween Morning: I Painted My Son’s Face (and He Taught Me Something About Healing)


This morning, I woke up to Halloween excitement. Theodore’s school doesn’t celebrate Halloween exactly; they call it Character Day, but that doesn’t dull his joy one bit. He loves Mickey Mouse, so we got him the full costume: ears, gloves, red shorts. While his dad made breakfast, I dug through storage for the old face paints.

A few days ago, the school sent a note saying all the kindergarteners should come dressed as Smurfs. I get it, class unity or whatever, but Theo is not into Smurfs. He’s never liked them. He’s not into cartoons with villains or scary characters, and the whole Smurf vibe just isn’t his thing. So I sent a quick note to his teacher, letting her know I didn’t have time to hunt down a Smurf costume and that Theo already had his Mickey outfit ready. I also mentioned he wasn’t really into Smurfs anyway, just so it didn’t come off like I was ignoring the assignment.

Then, the day before Character Day, Theo told me he spoke to his teacher himself. “Mommy,” he said, “I told Miss Cunningham I was going to be Mickey Mouse instead of a Smurf, and she said it’s okay.” The way he said it, calm, sure, no hesitation, just made me pause. My little five-year-old had advocated for himself. Kindly. Clearly. Without fear. And I just smiled, realizing what a big deal that was, something I never felt safe doing as a kid (and honestly, not even as an adult before lots of therapy and coaching).

This morning, I sat at his tiny table, paintbrush in hand, debating for a second if I should paint his face. Is that allowed? Some old rule whispered in my head, but I pushed it aside. This is HIS childhood. This is the FUN part. I started drawing the black circles around his cheeks and forehead, and gave him the little Mickey nose. He grinned the whole time. No squirming, no complaints. Just pure joy.

I watched him admire himself in the mirror, all proud and hype, and it hit me how different his experience is from mine. I don’t remember many Halloweens from my own childhood. My mom was already sick when I was little, and by the time I lived with my godmother at seven, after my mom died, Halloween wasn’t a thing. She’d bring home a bucket of candy instead of letting me go trick-or-treating because my neighborhood wasn’t safe. But also, no one really made the time.

I told myself that was enough, but it wasn’t. It was never about the candy, it was about the moment. The face paint, the costumes, the excitement of walking down a block full of lights and strangers who smiled at you. I only had one real Halloween like that, with my uncle and cousins in Bay Ridge when I was about thirteen. My cousin threw a colorful wig on my head and turned me into a clown. It’s one of the only Halloween memories that stuck.

Now, decades later, I’m sitting at Theo’s tiny table (ouch, knees and back) watching my son live the same joy I once wished for. His dad helped put on his coat, and Theo walked to the door, confident and hype, ready to show the world his Mickey Mouse self. I stood there, smiling, realizing what a big deal that was for both of us.

After they left, I stood by the door for a moment, listening to the sound of the car pulling away. Lydia was still sleeping upstairs. The house was quiet again. I sat on the edge of the couch, still holding the paintbrush, feeling full of love.

I’m realizing that parenting my kids is simultaneously healing my inner child. Watching Theo have the Halloween I never got felt like rewriting an old memory. I used to think legacy was about what I could leave behind: the financial security, the college fund, the structure. But now I see it’s also about moments like this.

It’s painting your kid’s face at his tiny table while breakfast sizzles in the background. It’s saying yes to something small that turns into something sacred. It’s showing him that fun is allowed, softness is safe, and joy doesn’t have to be earned.

I’m proud of how I’m raising him, not perfectly, but consciously. I know what it feels like to be a child asked to grow up too soon, and I’m undoing that, one moment at a time. The reflection that came to me as he left for school was simple but strong: I’m doing my best to give my children the emotional and mental foundation I didn’t have. That’s my legacy.

He walked out the door as Mickey Mouse (or as he would call himself, Theo Mouse), and I stayed behind, feeling like the little girl who finally got to plan her Halloween costume and get her face painted. This time, the memory belongs to all of me, the mother and the child I once was.



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