Trick-or-Treat, or, The Most Bittersweet Halloween

Halloween has always been one of my favorite holidays.

Which can be chalked up to either my secret fascination and childlike adoration of chocolate cupcakes with orange frosting or, on a much more profound level, the idea of dressing up and pretending to be absolutely anything I want to be without social repercussions for one night of the year.

Perhaps it’s because it suggests the end of autumn. While autumn stretches deep into December, visually and emotionally it seems to come to a quiet end around Halloween. The trees are no longer bursting with vivid colors; they’ve become skeletons â€" all limbs and no foliage. Meanwhile, people seem to subconsciously switch gears as they let go of corn mazes and apple picking and refocus their attention on the holiday stretch that the last two months of the year have come to embody.

Perhaps my love of Halloween also stems from the significance of another closing chapter, from another change that is as inevitable as the seasons. Halloween also signifies the end of another year of life for me, and the beginning of another. While my birthday falls two days after the holiday, my parents always made sure that celebrations for it were a three-day affair, starting on Halloween, coursing through the first of November, and ending triumphantly on my actual November second birthday.

This year Halloween is a particularly bittersweet event as it not only indicates the end of a quarter-century of my life in this world; but, it also is the end of a lifelong bet with my mom.

I have never not loved trick-or-treating. My Mom used to pick up my sister and I from school and we’d rush home to put on our costumes before visiting all the aunts and uncles who lived in town to do some trick-or-treating, and for me, birthday gift collecting as well.

We’d save my grandparents for last. My mom’s parents always made sure that whatever our favorite candy was at that moment, they had for us in abundance. Meanwhile, my dad’s parents always made all the grandkids (and there were a lot of us) brown paper bags filled with a juice box (a tradition started by my great grandmother, or “Grammie†as we called her), popcorn balls, gum, peanut butter filled crackers and other really random not-particularly-Halloween related food items. She’d line up the brown paper bags and write our individual names on them.

Windows rolled down, a pillowcase full of candy from my family sitting at my feet; I used to revel in this final day of October as we drove home for supper before my dad would take us around the neighborhood for more candy begging. I always joked on these drives home that I would go trick-or-treating forever (as little kids are prone to making such grandiose declarations)! My mom’s response was that if I could go trick-or-treating until I was thirty, she’d give me fifty bucks. I’m sure she was joking when she first said it, since thirty, when you’re a kid, seems like a hundred years away, but it stuck somewhere deep in the recesses of my then young brain.

As I entered high school, still trick-or-treating despite how lame my friends thought it was, my mom told me kindly that maybe I should go to a Halloween party instead, or, maybe even have some friends over to watch horror movies and eat pizza with â€" something like that. “But, you said,†a wide-eyed teenage me would begin, “that you would give me thirty bucks if I could go trick-or-treating until I was thirty.â€Â

My mom had no response. She had, after all, made that claim. So, I continued to trick-or-treat through high school, always starting at my grandparent’s houses before conning some friend to come with me around my neighborhood. They, I know, were secretly exploding with excitement that they had an excuse to be a kid again for the night as their parents had long ago stopped allowing them to go as it was seen as “childish.â€Â

As I was leaving the house to go trick-or-treating in college (and then out to the bars, of course, so I could partake in drunken Halloween revelry), my mom blocked the door frame, her eyes burning with impatience. “Give it up, child of mine,†she demanded.

I glared at her. “Never. You said fifty bucks. And as long as I still look like a teenager, I’m going trick-or-treating. Deal with it.â€Â

My sister became my cohort in these Halloween adventures, as my friends absolutely refused to go trick-or-treating anymore, but encouraged me as everyone then knew about the bet my mom had made with me. And so we’d hit up the grandparents, who would roll their eyes at us. We’d visit my dad and stepmom, who would roll their eyes at us. And then we’d visit our old neighborhood, and (after rolling their eyes at us) would ask, “Don’t you think you’re a little old to be trick-or-treating?â€Â

Yet, still, they’d hand us over candy.

A couple years ago, my sister and I showed up at my mom’s house. “Trick or treat!†We yelled, holding out our pillowcases (with our favorite candy from our mom’s mom; and our brown paper bags of goodies from our dad’s mom â€" our grandfather’s having passed on).

“I will give you thirty bucks right now in cash if you stop.†My exasperated mother said as she dropped more of our favorite candy into our bags.

“You told her fifty bucks,†my sister chipped in.

“THIS ISN’T YOUR BATTLE!†My mom exploded at her before calmly turning back to me. “Thirty bucks, Loin Fruit. Take it now.â€Â

Continued in comments . . .