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Author Richard Ray's son, Phil, center, in black bodysuit, participates in his final middle school Halloween parade.
Richard Ray
Author Richard Ray’s son, Phil, center, in black bodysuit, participates in his final middle school Halloween parade.
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Lukewarm coffee spilled from my thermos and onto my hands as I jogged down Clark Street, my boots splashing in the dingy puddles. Work emails had kept me from leaving my home office in a timely manner, and I was in jeopardy of missing a paradoxically trivial and soul-anchoring moment in my life: my 13-year-old son’s final middle school Halloween parade.

For most of the past decade, on Halloween morning, I would make my way to the rubber track next to the playground at my son’s school for the annual march of ghouls, goblins, YouTube phenoms and video game characters. It’s the same playground where my son cracked his head as a kindergartner; he had to get staples in his little ginger scalp. All the parades can be condensed succinctly into a 10-second montage of my son in varying states of gangly glory — dressed as a cross between Iron Man and Spider-Man (Spiron-Man, we called it), a Minecraft creeper and a hooded, scythe-wielding specter, all waving to me and squeaking, “Happy Halloween, Dad!”

When your kids are little, the milestones are relentless: They roll over, they crawl, they begin to walk, they cut teeth, they go trick-or-treating the first time and so on. But as they approach adolescence, the changes are subtle and fewer. Before you know it, a significant chapter has ended for you and your child. You are both different people. The paths you two walk slowly begin to diverge, and — as a father — your role begins to shift from protector and reacher of tall shelves to a consultant on proper decision-making and homework authoritarian. Hugs will always be in surplus but perhaps with less frequent purchases.

Reaching this stage as a younger, single parent has often left me feeling unmoored. Like a bedsheet ghost fading into the night.

At the school, I wove my way through the parents to get closer to the track as some costumed kindergartners appeared. They streamed out of their classroom doors, the same doors my son used years ago while wearing his little blue and white school uniform, his backpack bigger than the rest of his body. He used to wear a picture of his mother on a lanyard around his neck then. He missed her so much while he was at school that it was the only way to soothe him.

Suddenly, a gaggle of 5-foot-plus monstrosities began filing out of the adjacent gymnasium doors. I recognized my son’s teacher and was relieved to see I had not missed the eighth grade portion of the parade. I looked for my son’s distinct costume — a black bodysuit with a cycloptic white eye adorned with sanguine droplets. (He would admonish me if I didn’t explain that he was Seek from the popular Roblox game Doors.) I watched as my son’s group of soon-to-be trick-or-treaters rounded the bend where I’d taken my place with the other parents, my son scanning for my face like he’s done all the years before.

“Hey, Phil!” I shouted, waving with one hand and holding my phone high over my head with the other to record the parade. “Happy Halloween!”

I could not see his face beneath the nylon mask, but I knew that he was smiling as he shot his hand up and waved back. Some of his friends waved to me, too. We all smiled. They marched on and trampled October’s fallen leaves.

And then, just as quickly as they’d arrived, they headed back into the school. I stood there as if I were waiting for something else to happen, the drips of coffee drying on the web between my fingers. Other parents visited with one another and began filtering out of the playground to get on with their days while I stood for a brief while, solitary and rudderless, before I turned away from the track.

I’d seen his final Halloween parade. Was it supposed to feel like this big of a deal?

I walked back home in less of a hurry. Inside our home are baby pictures, toys he plays with less and less and his Green Blanky — a constant companion he’s had since he was a newborn. There I waited for him to come home and deliver the verdict as to whether he wanted his old man to go trick-or-treating. Maybe he would be taking off with some of his buddies instead. I was left in suspense, counting down the minutes for the dismissal bell as eagerly as the students.

He did, in fact, ask me to come — but I stayed a good block’s distance behind with some of the other parents. I savored the moment and didn’t take my phone out of my pocket save to take a few snapshots of him and his friends in their costumes.

At home, he dumped his candy on the kitchen table and left a celebratory imprint of his face in the crinkled wrappers. We had dinner and watched old “Treehouse of Horror” episodes of “The Simpsons.” He went to bed with a final “Happy Halloween, Dad.”

And then it was over.

Many times, when I have protested the inevitable, my child with the old soul has told me, “I can’t stay little forever, Dad.”

He’s right — and I know it.

I’ve been raising him for a long time in this city, and it’s given me such a profound purpose, holding the tiny hand of that little ghoul. Now that he’s mutated into a teenage monster, I can’t help but wonder what comes next in our father-and-son adventure, in which the ceaseless advancement of time becomes more subtle, more nuanced. In which all of a sudden you’re standing outside your kid’s final Halloween parade covered in coffee stains, dwelling somewhere between aching nostalgia and boundless pride.

In a place where all that’s left to say is this: Happy Halloween, Phil.

Richard Ray is a writer and media professional in Chicago. He formerly was an editor for WMAQ-Ch. 5, a reporter for the Chicago Tribune and a dishwasher at Glenn’s Diner.

Submit a letter, of no more than 400 words, to the editor here or email letters@chicagotribune.com.