Trick-or-Treating Through the Years (and the Candy Negotiations That Follow)

by Maria Williams

Here was my Halloween Night last night. It’s 6:00 p.m. on a cold kinda rainy night. Of course it was, right? I’ve got my 12 year old deciding if he’s “too old” to go, but still wants the candy and another who is so excited screaming “Halloween is my Superbowl” as he grabs his pillowcase. I am standing by the door holding my hand warmers, a travel mug of coffee, and a questionable amount of enthusiasm because the weather sucks. That’s trick-or-treating with kids in the growing-up years, equal parts nostalgia and negotiation.

The Costumes Change, the Chaos Doesn’t

Gone are the days of perfectly coordinated costumes. Greyson doesn’t want to match anymore (“Mom, that’s cringe”), and Hudson usually insists on something that involves fake blood and LED lights. However, this year he was a banana because he thought it was hysterical. Well, it was and I loved every single minute of it. Did I mention Greyson just wore all black and was a “Shadow” this year? Talk about a questionable decision, but I pick my battles.

You try to keep up, reminding yourself that even though your “family costume era” might be over, your “mom with a flashlight and backup candy stash” era is thriving.

The Full-Circle Halloween Friendship

How lucky and I? My best friend Jill, who’s been in my life since pre-school, just happens to live across the street. Our boys have grown up side by side, and this Halloween we hit the neighborhood together. I usually pass out candy, but left Nick to do the job this year.

There’s something about walking those same streets with your best friend while your kids do what you used to do that feels like time winking at you. The boys are out there comparing candy, and Jill and I are “taste-testing” the adult snacks that our sweet neighbors hand out — cider and sometimes something stronger tucked in a red Solo cup. We laugh about how we’ve gone from trick-or-treating teens to the moms yelling, “Stay together!” and “Say thank you!” It’s a full-circle kind of magic that no Pinterest porch could ever top.

Candy Economics 101

Once the bags are dumped on the floor, the real fun begins. There’s trading, bartering, and huge smiles because my kids don’t see this much candy all year long. Greyson’s offering three Kit Kats for one sugar filled gummy. Hudson’s offering his brother anything he wants because he likes it all. You’re just trying to quietly steal a mini Snickers without getting caught.

Somewhere in the middle of the chocolate negotiations, you realize the candy doesn’t matter, it’s the ritual. The running, the laughing, the “wait up for me!” moments that remind you they’re still your little boys, even if one of them went trick or treating with his friends so he was not seen with you or his little brother, the banana.

💡 Pretty Truth Moment

The trick is realizing that trick-or-treating isn’t really about the candy, it’s about holding on while they let go, one sidewalk at a time.

When the Porch Lights Go Out

There’ll come a Halloween when they both head out with friends instead of me. But not yet. This year, I still get to walk beside Jill, hear Hudson’s giggle when someone drops in an extra candy bar, and see Greyson’s smirk when I ask for my “mom tax” in chocolate as he walks past me like he doesn’t know how I am.

So here’s your reminder: throw on the cozy sweatshirt, grab the sneakers, and walk the block with them while you still can. The candy won’t last, but the memory will.

Because Halloween, like childhood, comes and goes too fast. but wow, it’s sweet while it lasts.

Like my vibe? You’ll LOVE my book!

Buy The Pretty Truth

Trick-or-Treating Through the Years (and the Candy Negotiations That Follow)

The Costumes Change, the Chaos Doesn’t

The Full-Circle Halloween Friendship

Candy Economics 101

💡 Pretty Truth Moment

When the Porch Lights Go Out

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