Let's Share Our Awkward Halloween Stories, Shall We?

Dressing like a normal person is difficult enough. Tell us we need to dress up as something non-human, clever, cute, and comfortable, and the task becomes monumental. Then, add to the mix gobs of sugar, potentially some alcohol, masks, and fake blood—and Halloween becomes a recipe for all sorts of debauchery, embarrassment, and jack o' lantern-related accidents. Let's share, here in our safe Takeout space.

It was a gender non-conforming costume.

Our family immigrated to Canada from Hong Kong when I was six, so I didn't grasp Halloween customs until relatively late into my childhood. It was the 1980s, so boys dressed as superheroes and girls were princesses. My level of Halloween comprehension was even more remedial: I only associated the day with frightening imagery, which is why as a 7- and 8-year-old, I chose to dress as a witch—the scariest boy witch in Greater Toronto.


Only after did my grade school friends poked fun at my costume, did I decide the following year I'd overcompensate with machismo. That year, pro wrestling's biggest show, WrestleMania, had come to Toronto, and Hulk Hogan was its biggest star. I fell hard for the pageantry and spectacle of wrestling, and the Hulkster was a larger-than-life cartoon character come to life. I cried when he was defeated by the Ultimate Warrior, as did many of my friends.

And so 9-year-old Kevin decided to go as his favorite pro wrestler, Hulk Hogan. I found the tightest yellow shorts I could. I cut a moustache out of blond felt. There were no Hulk Hogan boys T-shirt at the department store, but I found the next best thing, a red shirt with a large W insignia—the WWF logo.


I was so excited. I practiced my poses, I Hulked up in front of the mirror, I recited, "Well you know something Mean Gene!"

I met up with some classmates to trick-or-treat in our neighborhood. And as soon as they saw me, they started laughing and pointing. I was so confused. They could barely muster a word from laughing so hard.

I picked out the wrong shirt. I was dressed as a chubby Asian moustached Asian Wonder Woman. [Kevin Pang] 

It was not a costume.

Attempting to make my own Halloween candy was my truest embarrassment, but here's another fun story.

I was a freshman in high school, and Halloween fell on a weekday. I went to an all-girls Catholic school where only the senior class was granted the "privilege" of dressing up in costume, so for me, Halloween was the same as any other day of the week.


I arrived home from school around 5 o'clock—after our literary magazine meeting adjourned, #nerdalert—and dropped my backpack to prepare for the first wave of trick-or-treaters.

The doorbell rang almost immediately. I opened the door to a group of three kids not too much younger than myself.

"Whoa, are you Britney Spears?" one asked. They all nodded their approval: good Britney costume.

I was confused, then looked down at my school uniform. The "... Baby One More Time" video was still relevant then, but it was decidedly not the look this sarcastic, Daria-loving middle school geek was going for. [Kate Bernot]

It was some bad-taste costumes.

For several years now, the highlight of my Halloween season has been the Dead Celebrity party my husband and I throw in our wood-paneled basement rumpus room. I am gobsmacked by the costumes people come up with: This year's winner was a Stephen Hawking, complete with wheelchair and talking iPad (I was a lame Virginia Woolf-era Elizabeth Taylor. I never win the costume contest). We had a few dueling Burt Reynolds, including my husband; last year we had a ton of Princess Leias, in honor of Carrie Fisher. Honestly, I'm just glad that people show up to my house year after year and seem to have a good time (as usual, this year devolved into a shouty karaoke free-for all after midnight).


Our various costume contest categories consist of Best In Show, Best Couple, Best Conceptual (this year saw the death of Lady Liberty, and the scales of justice), and Warmest Corpse (person who has died closest to the party date). But the most controversial category is the Worst Taste award. It was created several years ago when a friend of a friend—a tall, lanky guy—showed up dressed as Jon-Benet Ramsey, complete with tiny cowboy hat and little white dress. This sounds so terrible, but it was impossible to look at him without laughing. He beat out my friend Bobby—who had carefully crafted a Captain Kangaroo costume, right down to a bunch of thrown ping-pong balls—due to the overwhelming swell of crowd support. After that, we made up a new Worst Taste category.


But that category hadn't seen its bottom yet: That showed up a few years later when someone showed up as Eric Clapton's kid, complete with head through a screen and a stuffed animal. She took the bus to the party; someone asked who she was, and when she told them she almost got thrown off the bus. She was obviously the winner of the Worst Taste award, but again, we didn't feel great about it or anything.

This year, the guitar player in my husband's jam band won Worst Taste by showing up as Charles Manson, with his wife as Sharon Tate. Considering some of our previous Worst Taste winners, it was almost tame in comparison. Happy Halloween, everybody. [Gwen Ihnat]