This week, I was traveling for business and spending time with my younger brother and his family in Chicago. We were sitting at the dinner table one night and started talking about Halloween. My two nephews asked me what my children were going to be this year and I gave the old school response that I was in the dark and we should text them to find out.

The next day, on my way to the airport, I thought back to when my children were younger, and of some of our favorite Halloween memories, and realized that time really does fly by in a blink of an eye.

My oldest children are twins and their first experience with Halloween was handing out candy while dressed up as a horse and a dog. Of course they were the cutest kids ever, as any parent would modestly declare about their children. However my very intelligent son got the idea in his head that he should be out and about just like all the other kids. So during one of the lulls in the hoards of trick or treaters, my almost two-year-old walked out the door and headed over to the neighbors to trick or treat. He’d made it to the first house all on his own. Fortunately our friends had a very enjoyable laugh at our expense since he was “unable to recite the standard verbiage.” So they knew something was up because he hadn’t been properly “trained” and they quickly brought him back to our home.


This adventurous, almost two-year-old is now almost 13 and of course now he wants to go out trick or treating alone with his friends for the evening, a frightening thought for any parent. I believe we’ve given him the tools/training to go out on his own and make good choices, at least for one evening, but the training wheels are officially being kicked off and there is no turning back.

So my son will be on his own this year, going as a couch potato – pajamas, robe and a clicker – while my daughter is leaning towards dressing up as Snow White.

My wife and I are bracing ourselves for this next adventure in parenting.

What’s the most memorable Halloween you’ve had with your children?


David is the Marketing Director for Right Start. He is the father of 3 with a set of boy and girl twins. He stays busying coaching his children in the various sports that they participate in. His partner in parenting is his wife, Heidi, who stays at home to manage their pre-teen children.

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2 Responses to Halloween Memories with My Oldest

  1. OH my word! That is totally something I could see Little Man doing. I recall my niece’s first trick or treating experience. We all had prepped her (or at least we thought) but when the first door was opened instead of holding up her bag and saying “trick or treat” she waltzed right on into their home. Her mom had to carry her out kicking and screaming. She couldn’t quite understand why we had to leave a home with so much candy. ;)

  2. I can imagine my oldest making a break for our neighbors in an attempt to get her hands on some treats when she was that age too. Madeline had just started walking a couple of weeks before her second Halloween and My favorite memory from that holiday was how she stuck her arms into the air to balance herself and took big leaning steps when she walked. She looked like a Ladybug King Kong.

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