Halloween through the Ages: Pumpkins to Teen Negotiations

WRITTEN BY BLAIR FJESETH

Halloween has a way of sneaking up on us parents. It’s a holiday that doubles as a quiet mirror, reflecting how parenting changes as our kids get older, one candy-fueled step at a time. At first, it’s all about our carefully-curated vision: the perfect costume and the safest route. But, as the years pass, the holiday evolves along with our kids. Suddenly, they have opinions, preferences and plans of their own, and what once felt like our occasion becomes a dance of compromise, negotiation and, eventually, trust. Halloween doesn’t just mark the calendar—it tracks childhood milestones, independence and the sweet (and sometimes sticky) way families grow together.

The Baby and Toddler Years: Halloween is all Ours

We pick the costumes, plan the route and orchestrate the sugar haul. Toddlers become tiny pumpkins, wobbly superheroes or whatever adorable thing we dreamed up, with our eyes always on the cuteness-to-practicality scale. And for those brave souls coordinating full-family themes with multiple kids? Hats off. There’s magic in those first unsteady steps, pumpkin buckets clutched tight, and in the pride of photos that will haunt (see what I did there) our social media feeds for years. I remember each of my babies’ first costumes like it was yesterday… though it definitely wasn’t. Since then, we’ve had Paul Bunyans, chickens, an inflatable Godzilla and countless other professions and characters in between.

The Middle Years: Negotiation Takes Over

Suddenly, our well-laid plans collide with requests for glittery tutus, face paint, fake blood or the last-minute costume idea change. Safety versus style, warmth versus authenticity… compromise becomes an art form especially in Montana. Will it be 80 degrees out or will we be trick-or-treating in snow?

The Pre-Teen Years: A Delicate Dance

By pre-teenhood, Halloween is all about autonomy, peer pressure and subtle rebellion. Kids have their own ideas, crews and strategies for maximizing candy, or social points. We step back, offer occasional advice on “costume appropriateness” and try not to kill the vibe. Our role now? Chaperone, chauffeur, occasional unpaid therapist. Candy moderation discussions are practically laughable, yet the tradition continues. They trick-or-treat in new neighborhoods, laughing louder than we ever did, and we realize the holiday — once entirely ours — now belongs, in large part, to them.

I remember carrying them from house-to-house to show them off. Then I carried the “too-heavy” candy buckets. Now, I trail behind like a low-key creeper (maybe that will be my costume this year), making sure they’re safe while letting them stretch their independence.

Through it all, I’ve discovered that Halloween teaches a simple truth: parenting changes. Our influence rises and falls, compromise becomes a tool and trust takes center stage. Still, the heart of the holiday stays the same — a chance to be whimsical, a little spooky and connected, however the age, phase or kid allows.

We get only so many Halloweens and none of those are guaranteed, so I say “Stay spooky, stay whimsical and stay present.”

Blair Fjeseth is a working professional and proud Montana mom. You can reach her at blairparker. inc@gmail.com.