The Invaluable Lessons Halloween Can Teach Our Kids

Joe DeProspero has two sons, a wife, and is complimentary birth control for anyone who sits near him in a restaurant. His writing has been described as “outrageous,” “painfully real,” and “downright humiliating.” He talks about the highs and unsettling lows of parenthood while always being entertaining and engaging in the process. Author of the dark comedy fiction novel “The Boy in the Wrinkled Shirt,” Joe is working on releasing a parenting humor book. He currently lives in New Jersey and can be emailed at or followed on Twitter @JoeDeProspero.

Growing up, I wasn’t a very popular kid. And like any prepubescent boy, that stuck in my craw. Looking back, it seems absurd. Why would I long to be idolized by people who willingly wore Z. Cavaricci pants and gained God-like status merely for having rich parents? But anyway, it was due in large part to my lack of rank and general absence of confidence that I anticipated one holiday a year more than any other- Halloween. It was the one day out of 365 that allowed me the luxury of being somebody else for 24 hours.

I know it sounds like a bad thing, but trust me, it wasn’t. Halloween served as a reprieve from an adolescence marked by mediocre grades, a modest group of friends, and an astonishingly dreadful track record with the ladies. None of that mattered on October 31st.

I took Halloween seriously, and still do to this day. I always scoffed at classmates who’d show up at my door wearing a football jersey, or worse, no costume at all. In my mind, Halloween wasn’t just a suggestion to embrace the mysterious creep within, it was an obligation to. I always took this time of year as a chance to allow myself to be scared, made to feel a little uncomfortable even. But most of all, have the time of my life doing it. And believe it or not, I think instilling the same tradition in my children will actually benefit them as they grow up.

I also think there’s a great deal that our children can learn from Halloween. Here are just a few of the learning points:

Be Creative

Of all days, Halloween is a day that rewards creative thinking. Since I was so into Halloween as a kid, my parents hosted parties at the house. One year, we even held a costume contest. Try as I might to remember what everybody wore that night, I only remember one costume. Jessica Dickson dressed as a giant Oreo cookie. She took home a prize. I was always partial to spooky costumes, but that one still sticks with me. Years later, I see people dressed in innovative, mind-blowing costumes like this and I’d bet good money that, as kids they were encouraged to put thought into their costume. Fuel a creative mind and you’re more likely to raise an inventive adult that harnesses individuality.

Know How to Have Fun

It sounds simple, but there are plenty of people who need to be taught how to enjoy themselves. Halloween practically forces you to have fun. And you’ll find that the majority of people who claim to “hate” Halloween aren’t people you’d want at your party anyway. Nothing makes me happier than seeing my son lick his proverbial chops in eager anticipation of All Hallow’s Eve. I intend to stoke that fire.

Go All the Way

Halloween not only gives children a public stage to show off their creativity, but it also tests their ability to follow through on something that isn’t an ice cream cone. So if your kid is attempting to put together a homemade Jack Sparrow costume but gives up halfway through, offer some encouragement to get back on the horse. It’s a fantastic opportunity to teach our children determination, while showing them the tangible fruits of their labor at the same time.

Don’t Take Yourself Too Seriously

This might be the greatest lesson that Halloween teaches our kids (and adults too, quite frankly). It reminds us that, at the end of the day, we’re all kids yearning to play dress-up, if even for one day a year. However, those of you with daughters dressing like sexy devils or kittens likely don’t embrace this whole dress-up concept. Can’t blame you.

So, next Thursday, when you’re trying to keep up with your proud son rocking the homemade Jack Sparrow costume, know that by embracing Halloween, you’re enabling their individuality, and that’s the best treat of all.

 My son, Antonio, at age 2 1/2, standing in front of the first door at which he “trick-or-treated” on his own

 What are your memories of Halloween, as a kid or an adult? Join the conversation by adding a comment below!

Not sure what you’ll be yet? Use our Halloween Costume Finder, and then buy your favorite Halloween costumes at Shop Parents. 

* Halloween photo courtesy of




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