My Three Worst Halloweens

By on October 31, 2017

Here it is, Halloween, and I’m reflecting on years past. I don’t want to be a Debbie Downer, since most of my Halloweens have been great, but somehow the most memorable ones are the ones that didn’t turn out too well. So here is a list of my three worst Halloweens.

1.) Where the hell is that mask?
This is definitely my worst Halloween. My youngest son Max was nine years old and in fourth grade. A few days before Halloween, we went to the costume store to get him something nice and scary. Every year, the children would parade around school in their costumes and then have a party in the gymnasium. Max, after deliberating quite a while as to what his costume should be, chose a very scary werewolf. You know the type — the wolf face with fangs, a torn shirt with hairy arms and protruding hands. For my little guy, this was the perfect costume. It’s the morning of Halloween and he brings down the plastic bag that had the costume inside. Now because of my bad parenting, we never bothered to have him try on the costume. So he pulls all the stuff out of the bag and there was no mask, only the shirt, the arms and hands. He basically looked like Steve Carell’s chest in the 40 Year Old Virgin. I ran to the costume store, but they weren’t open until 10am, when the parade started. I felt so bad. My little guy had to go to school without a costume. To this day I get sad just thinking about how I let my son down on what is a big day in a child’s life …

2.) It’s in the bag.
Now we go back a few (okay, many) years to when I was six or seven years old. I grew up in a suburb of Milwaukee, Wisc., and as you can guess, by the end of October the weather can be pretty unpredictable. This night was cold and rainy, which was not uncommon for this time of year. When I was a kid we only had paper bags; plastic bags were not available yet. A big part of this story is my dad who, rain or shine, would take me trick-or-treating and was such a big part of my growing up. He managed, through the rain, to take me around until my bag was very full, at least very full for a seven year old. Now, across the street from Bear’s Reliable Pharmacy, the bottom of my bag burst open from all the rain. Candy flew everywhere, a real disaster. Again, I’m dating myself, but the candy was not wrapped in individual wrappers like today. So all I had left was an inedible mess. I added to the rain by balling my eyes out. Imagine going home without any candy. My parents made my sisters, who were four and five years older than me, share their candy. That went over about as well as a lead balloon. I suppose, in retrospect, the only good thing about that Halloween was not having any cavities that year.

3.) See ya later.
This one Halloween is fairly recent. I had had a run of Halloweens and trick-or-treating from the time my oldest son Ryan was two to the time my youngest son Max was 12. This was a span of 25 fantastic, wonderful years. I would often meet up with friends and go as a group. Halloween was one of my favorite events of the year. But the sad day came when I was no longer invited out to trick or treat. The night started out like most other Halloweens. My son put on his costume, some sort of warrior outfit popular with seventh graders. We went and picked up three of his friends and drove to a neighborhood that the trick-or-treating was easy, meaning lots of houses close to each other. It was maybe 10 minutes later that my son and his friends ditched me. That’s right, adios dad, see you at home later. It struck me that I would never get to trick or treat again. I believe they say all good things must come to an end. Oh well. Guess I’ll just have to have another kid … hehehe, that’s not going to happen! Maybe some day with grandkids …

Let me know if you have any horrible Halloween stories to share. Or am I alone in this scary night being a bit scarier?

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