My Top 5 Most Awkward Halloweens

I had a lovely post all written out for today, perfectly catered to reflect my awkwardness, and then my work computer crashed and I was told the files were not recoverable. So, alas, here we are. It was important to me to get a post out today since I missed last week, so I guess I’ll just have to wing it.

Halloween has always been such a weird time for me. You’d think it would be my favorite holiday, as it combines two of my favorite activities: being overly theatrical and soliciting candy from strangers. But for whatever reason, Halloween always leaves me with a particular, profound sort of emptiness. Maybe it has never lived up to my expectations. Or maybe I just associate it with less than fond memories.

I’m really looking forward to the weekend ahead of me: I’ll spend time with friends I haven’t seen in a while, I’ll get to sleep next to my boyfriend, I am entirely too proud of my costume. But I have no doubt I will still feel weird and moody and uncomfortable and somehow lonely. Because that is what Halloween does to me.

Anyhow, here are some of my awkward Halloween memories to share with you.

The Time I Thought I Turned My Dog into a Pumpkin

The first Halloween I have committed to memory is when I was three years old. I was dressed as a fairy princess and was upset that I wasn’t accomplishing real magic, despite having a magic wand in my possession. My father, bless his heart, convinced me that if I closed my eyes very tightly, I could turn my dog, Brittany, into a pumpkin. While my eyes were shut, my father very swiftly put Brittany into another room and put a pumpkin in her place. I opened my eyes and my jaw dropped to the floor, but my reaction was not what my father was hoping for. I became grossly upset with myself, worried that my dog was gone for good, that she was trapped in a pumpkin and terrified, and that I had used my powers for evil. Of course, my dog did come back, but I retired my wand that day, and a part of me thinks that the reason I’m so obsessed with dogs is my penance for trapping my dog inside a pumpkin. And my punishment is that they usually ignore me, for I need their love way more than they need mine.

The Time I Learned a Lesson About Society

When I was five or so, I really wanted to be Belle for Halloween. She had brown hair, brown eyes, and liked stories, so we were essentially twins. My mom, at the time, told me that all Halloween stores were out of the costume, but I knew the truth when I saw my skinny cousin wearing the costume a few weeks later: they didn’t make the costume in my size. Chubby girls couldn’t be Belle. I will believe in progress when I see a movie with an overweight woman as a romantic lead, and not a single comment is made about her weight. Dear world, promote health, promote happiness, and stop making women feel like shit about themselves all the time and then telling them their insecurity is unattractive. You’re unattractive, world.

The Time That Somehow, Every Single Year, I Managed to be Either the Only Kid in School Who Wore a Costume, or the Only Kid in School Who Didn’t


The Time I Went Trick-or-Treating by Myself

Up until the eighth grade, I only really had one close friend, and we went trick-or-treating together every year. But one year, in the fifth grade, she had pneumonia and couldn’t go. I had two options: I could mooch off of my brothers’ candy, or I could go by myself. Destiny’s Child was big at the time, and so naturally I valued myself as a strong, independent woman, because Beyonce told me to, so I went by myself. I’m not sure if there is a sadder sight than a 10-year-old going door to door, her mom waiting for her at the curb, with her head hung in defeat because she realized this was incredibly boring, miserably asking, “Trick-or-treat?” in her voice that is 50 years ahead of her body, development wise. This is the first time I can recall having the weird Halloween feelings; feelings of overwhelming loneliness that are evoked by the sights and smells of Halloween to this very day.

The Time I Had Alcohol

My first alcohol experience was on Halloween. I had approximately four sips of Kahlua, so naturally I felt wasted. I ended the night eating an entire bag of Oreos and watching Donnie Darko.

So, combine a dog’s soul forever encased inside a vegetable, the denial of my royalty due to unfair discrimination against kids who love to eat, a slew of memories of getting it wrong, a lone trick-or-treating, and the mind-fuck that is Donnie Darko, and you get one awkward time of year.


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