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The Hairpin Halloween Advent Calendar: Halloween Confessions

It’s our firmly held belief that Hallowe’en is far more important than Christmas, and therefore more deserving of a countdown calendar. It is, after all, the most wonderful time of the year: there are parties and costumes and terrifying things like Martha Stewart, and candy and then more candy and then even more candy, and your ability to consume that much candy is a marvelous thing to behold.

So, in celebration of the Highest of High Holidays, we’re creating our own version of a Halloween Advent Calendar. We’ll post one Halloween-y piece a day — including on weekends — in the three weeks leading up to October 31. Why three weeks? Because three is a spoOoOoky number!

To kick things off, we asked some of our contributors to share their darkest Halloween secrets.

Thyra Heder
In second grade I spent two weeks making a globe costume with my mom. It was fabric with blue water and green land, and built of concentric plastic rings so I could fold it up like a china ball lamp to fit through doors. I had not only hand-drawn each continent but also traced it in glow-in-the-dark puffy paint in case anyone turned off the lights. I was super proud of myself and my costume until the moment I stepped into my classroom and saw a sea of store-bought Princess Jasmines and half-assed pirates. I burned with shame. I was terrified that people would think I had spent weeks on my costume, which I had. Red-faced and panicky, I flattened out the globe and shoved it behind the coats. I had to put a coat over it, too, because it was glowing. I told my teacher I had forgotten my costume, and she gave me a paper plate. I drew a lady’s face on it and made it a mask, and when our class marched our costume parade through the nearby nursing home, I told people I was a gypsy.


In the early aughts, I attended a party at the Soho apartment of a rich guy. For some reason neither of us can recall or morally rationalize to this day, one of my guy friends and I decided to sneak into the bathroom and hide in the shower. Don’t do this! For many reasons, one being that while it might be easy to get into a shower at a party, it’s much harder to get out of the situation without being caught. We found ourselves frozen for a never ending fifteen minutes while we waited for person after person to come in and pee – apparently we didn’t think about the fact that a line might form after our prank. We both were shaking with pent-up laughter, and tears streamed down my face as I tried so hard to be quiet that I couldn’t even look at my friends’ arm or his shirt, much less make eye contact. I just stared at the bathtub floor, trembling, tears dripping on the porcelain as I tried to think of a way out. We were finally able to slip out during a break in the line (whispering “go! go! go! go! go! “) and it just looked like we’d been in the bathroom together, which wasn’t suspicious at that particular party. Then we laughed harder than I’ve ever laughed in my life.

In case you’re wondering, no, nobody did anything embarrassing, toilet-wise, and we wouldn’t have known who they were anyway. They just each peed normally, washed their hands (for an endless amount of time), adjusted their hair and faces in the mirror (for an endless amount of time) and left. To this day, when my friend and I talk about it, we can’t figure out how we got in that shower or whose idea it was. And to this day, I check the shower for pranksters at every party I go to. Which is something I’d already done my entire life already, but now I know that yes, it really happens. People hide in showers at parties. You’ve been warned. 

Jim Behrle
One time, I was wearing a Santa suit on the subway and there was a little boy, maybe five. And he was freaking out. And his mom was like, what’s the matter? And he said “What’s Santa doing on this train?” And his mom was like “It’s just a guy dressed up for Halloween!” And the kid was crying. “No! It’s too early for Santa!” And his mom looks at me like I took a dump in her purse. The kid cried and cried. I got off a stop early and waited for the next train.

Angela Serratore
I was Halloween Queen three years running in the parade at my elementary school, and on year four the other parents complained that it wasn’t fair, and the teachers were like, we know, she’s just so good at Halloween!

Jen Carlson
There was a time in college when I had Bell’s Palsy from Lyme disease — half of my face was paralyzed and drooping, and I had an uncontrollable drool and would also fall down a lot because I couldn’t always feel my limbs, but I went out anyway. For Halloween I put on a wig and glitter and was a “70s disco person” — it was an admittedly shitty costume, but aside from that the combination of me wearing a wig + my face being paralyzed truly ended up confusing everyone who didn’t know I had Bell’s Palsy. Plus, at the time there was this new girl who I didn’t like who was hanging around with my then-boyfriend’s group. She was so annoyingly upbeat and of course had this really put-together costume on that night. I had someone take this photo, which still cracks me up.

Jane Marie
A few years ago I didn’t dress up for Halloween and everyone thought I was going as Janice Dickinson. And then I dressed as Allison, the keyboard cleaner addict from Intervention, and everyone thought I hadn’t dressed up.

Katie Heaney
My embarrassments usually have to do with excess enthusiasm, with a particular energy reserved toward days on which I am led to believe there will be mass participation in coordinating dress. This is okay NOW, but the effort you’re socially allowed to put into your Halloween costume is an upside-down bell curve against the axis of age, the sinking middle aligning with years 10 to 22. At the low point, in the seventh grade, my aunt sewed me a gorgeous queen’s ball gown to wear for Halloween. It was incredibly ornate: forest green silk with black velvet floral running across it, a pearly bodice with gold ruffled trim, and a hoop worn underneath that made the dress hang out a full foot on either side of my body. This was a problem in the hallways. My aunt also made me a velvet headband with fake pearl trim and a veil that hung to the place where, in seven years, my hips would be. This I wore on top of my haircut that year, which, unfortunately, can only really be described as “Hugh Grant in Notting Hill.” I have a picture from this day, and I don’t know where it came from because I am not meant to be a part of it. There are three of the cool girls in the foreground, dressed simply as hippies and pop stars: in their normal tank tops, but with feather boas and/or braids. In the very back corner, hardly noticeable, I am sitting at my desk: tiny and wan, drowning in yards and yards of fabric. I am smiling wearily, with just a quarter of my mouth. I do look like a very small queen, exhausted by royal restriction, unable to relate to my commoner subjects. It’s probably my favorite picture of me that I have.

Jaya Saxena
I’m not sure if this is a confession, but my technical first kiss was at a Halloween party. I was in 6th grade and my friend was hosting a party at her apartment, and my crush was there. We were playing spin the bottle, and when it was his turn, as a joke he started pointing the bottle around the circle, saying who he’d like to kiss and who he wouldn’t. When he turned to me, he pointed the bottle at my face and yelled “HELL NO!” I wonder if it had to do with my white lip gloss. Did I mention that my birthday is October 29, which happened to be a weekend that year, so I’m pretty sure this also actually happened on my 12th birthday? Ed: Wait, but so did he kiss you? He did! The bottle ended up landing on me later, and he did, very quickly and closed mouthed, and made a point of wiping his lips afterward. It was about two years until I was kissed again. It’s okay, the Crush is now sorta ugly and lives in Canada!

Katie Walsh
I “forget” bottles and jars of fake blood all over my friends’ houses when they host Halloween parties. I’m a fake blood fairy.

Nicole Cliffe
In fourth grade, there was a “scariest costume” award. I was just a normal witch, but just before they started the competition, I had a brainwave and pulled my black turtleneck up over my face and tucked it under my hat. I couldn’t see, or anything, but, trust, I was scary. And I won! And then this bitch, Carla, was mad, because her parents had dropped forty bucks on an actual costume, not just a black turtleneck and a broom, so her friends hounded me relentlessly until I gave Carla the thirteen dollar prize, “because she deserved it.” Carla was a real bitch, and I was a pussy.

Rebecca Jane Stokes
In the year between finishing my undergrad and moving to New York for grad school, I was, to put it mildly, spiraling. I lived at home with my long-suffering parents, worked as a temp, and would come home — depressed — to order excessive amounts of footwear via eBay before hunkering down for a three hour block of Nanny re-runs. It was a magical time. Since I didn’t have much “going on,” the holidays took on much higher stakes — I relished them, I planned. That particular Halloween, I went all out, and over the span of four or five weeks put together a full Batman Costume (complete with head-piece and mask). Its cost in total is a sum of money that is too shameful to even consider disclosing. To be fair, it is challenging to realistically costume oneself as Batman when you are five foot two and blessed in the breasticle region. On the night in question, while my parents hosted a small party of friends, I took to their second floor balcony, where I played Danny Elfman’s Batman theme on a loop from my boombox and hurled miniature candy bars at passing children bellowing stuff like “CITIZENS OF GOTHAM, I COME BEARING SUGAR,” and, rather oddly I now realize, “FEAR ME!” I continued in this manner until I hit a baby-princess being carried by her father. As they fled, terrified, I retreated to the den in a twirl of cape to finish the candy and watch Rocky Horror alone. I drank scotch to dull the memory of the patina of evil I had bestowed to Bruce Wayne’s good name. I woke up the next morning in costume. I still have that looped CD.

Edith Zimmerman
One year when I hosted a Halloween pre-party before the Big Party at a Super Hot Guy’s house, I got so nervous that it wasn’t going to be fun or cool that I drank far, far too much of the punch that I’d made. Afterward, we all got on the subway to go to the guy’s party, but when the train came and everyone got on, at the last minute I ducked back, went home, threw up, and went to sleep. The next morning my friends were like where did you go, you can’t just do that.

I hooked up with my partner for the first time on Halloween.  While she was on a date with my best friend.

Jolie Kerr
1. I discriminate against smiling jack-o-lanterns.
2. I enjoy wearing trampy-looking Halloween costumes and resent the annual argument that goes something like this, “If you want to dress all trampy looking, you should own that and not use Halloween as an ‘excuse’ to do so.” But not as much as I resent the flip side of that argument that tells me not to wear trampy-looking Halloween costumes at all. My body, my self!

Lili Loofbourow
(Not Halloween so much as costume-related.) One year in college, I lived kitty-corner from the Shrine Auditorium, where they used to do all the awards shows, and it was annoying as all get out. Helicopters overhead for hours on end. Police wouldn’t let you drive onto your own street unless you showed them a bill proving you lived there. (I refused to do this, both out of principle and because the bills weren’t in my name.) Then there were the crazy people who spent days camping so they could sit on the bleachers and watch the red carpet arrivals. These people, we all agreed, were terrible. Shallow, star-obsessed, loser Los Angeles. One did not care that dozens of celebrities were going to be glittering up the place across the street if one was, in any way, a sentient being. One simply didn’t. It wasn’t done.

But I secretly did care. I wanted to see the tiny fetching creatures of glam and sex. So without saying anything to my roommates, I hatched a plan. I braided my hair, put on a frumpy dress (with a print that erred on the bumpkin side of floral), and some minimal makeup to cover my zits. Country bumpkins always seem to have good complexions. Dressed as I imagined Hannalee might on a date, I strapped on a boxy and unattractive purse and walked to the corner where all the celebrities were arriving.
It was early. Some limos, but not too many. No one I knew. A security guard walked over and asked me my business. “Oh, hello,” I said, “I’m waiting for my date to pick me up!”

“Your date?” he said.

“Yes!” I said. He scowled.

“Young lady, I don’t know if you understand what’s going on here.”

“It looks busy!” I said cheerily.

“It’s the EMMY’S,” quoth he.

“Oh!” I said. “That’s exciting! Who’s hosting?”

“Miss,” he said, “what I’m telling you is that we’re not letting traffic through here. Where was your date supposed to pick you up?”

“At this intersection,” I said.

“Can you call him?”

(This was before cell phones were everywhere.)


The security guard scratched his chin.

“I don’t know what to do,” said I, scrunching my face into what I hoped looked like worry.

“Well,” said he, “do you know what he’s driving?”

“Uh,” I said, thinking as fast as I could of a make and model I’d never seen in LA, “a red Datsun truck.”

“We’ll do what we can, miss, and if we see him, we’ll wave him in. No promises.”

“Oh, THANK you!” I said. I stood on my corner and watched, occasionally pretending to scan the horizon for my date. Lots of people arrived. Most of them were not famous. I did see Callista Flockhart get out of a limo with Harrison Ford. She was small.

My plan would have worked brilliantly if it weren’t for the irritating fact that Ned (that was the guard’s name) had a big heart. He told the other security guards about me, and they all kept looking in my direction with tragic expressions. It is disconcerting to be looked at in this particular way by a group of security guards. I was sure they suspected something — maybe they thought I was a terrorist? I started doing a nervous leg shuffle. Ned walked over.

“What time was he supposed to pick you up?”

“6:30,” I lied.

“Huh,” said Ned. He shook his head and walked away. I checked my watch. It said 6:40. Understanding dawned. The guards were watching me get stood up. Time to act the part! I started tapping my foot impatiently and looking at my watch.

Now, I don’t know if you’ve ever tried miming being stood up, but it gets real repetitive real quick. After five minutes of compulsive, tic-like foot-tapping and watch-checking, I got nervous for real again and worked the leg shuffle back into the routine. I credit the leg shuffle with getting to Ned — it really is an effective piece of theater. A few minutes into it he walked over again, clearing his throat in the style of an embarrassed pall-bearer.

“Have you known this guy long?” he asked.

“Not that long,” I said. “This was our third date.”

“Huh,” Ned said, noting my use of the past tense, and stood for a few seconds, silently. “Well, we’re keeping an eye out. Don’t you worry. He’ll turn up.”

Another 10 minutes went by. Some ladies in gowns arrived with their dates, but no celebrities. None. Just bored limo drivers and the gaggle of security guards, who by this time had gotten friendly with the limo drivers and explained my situation. When 35 or so men are politely pretending not to look at you on your corner, you realize that they aren’t really very good at pretending. One big man with a neck-roll kept talking into his walkie-talkie, then ever so slightly shaking his head. Impossible to remain calm when that sort of thing is going on, and I didn’t. Frozen and on the spot, I thought up a few new Impatience Markers. My favorite was occasionally rummaging inside my bag for something I’d apparently lost. I wouldn’t find it, and would look up, grim, despondent, empty-handed. I was stacking on the drama because things were getting serious: it had been half an hour. I needed to transition to anger. I’d abandoned the foot-tapping; we were past that. I crossed my arms and glared down the block, a woman scorned. I visualized a red Datsun truck. I visualized it hard. And then I thought about Robert Downey Jr.

This was all taking a lot of energy. C’mon, I thought. Brad Pitt, Jennifer Aniston. Where ARE you guys?

A limo turned onto the block. I perked up. Was it them? It wasn’t. My face fell.

Ned walked over, somber. All the drivers and guards watched him as he crossed the street and looked at a point next to my left foot. “Maybe he figured out the Emmy’s are going on,” he said. “I bet there’s a reason. Maybe we missed him.“

His walkie-talkie crackled.

“What?” Ned shouted into the walkie-talkie.

I don’t speak static, so I have no idea what the walkie-talkie person was saying.

“YES!” Ned yelled. “We found him! The guys just spotted the red Datsun!”

“What?” I said.

“Two motorcycles just went after him. They’ll tell him you’re here.”

“Oh!” Adrenaline was doing cannonballs into my blood.

“WE FOUND HIM!” he roared at the guards and drivers. They cheered.

“Oh!“ I said. “I’ll just go to the next block and meet you all there?”

“Okay!” said Ned joyfully, and turned back to the walkie-talkie.

“Thank you!” I said, and turned around and ran. But I didn’t run to the next block. I ran to the door of my building, which was some 60 feet away, and perfectly visible to the limo drivers and security guards, some of whose mouths were open, still mid-cheer. I swiped my card with shaking hands and glanced back at Ned, who was looking at me, uncomprehending. I tried to mime that I was way too angry with my date to see him now, even if the two guards on motorcycles dragged him into the Emmy’s. Who drives a red Datsun truck, anyway?

I’m sorry, Ned.

I was a junior in college and dressed up with a friend as “Hoes In Different Area Codes” from the Ludacris song (I went as 203, she went as 914 — Greenwich and Scarsdale. We thought we were hilariously ironic). I had these horrendous sunglasses on, and we went to a dive bar, and some drunk guy wanted to wear them. I kept telling him no until he gave me a $100 bill as collateral. Eventually I just left the bar and went home with his money.

Last Halloween, the endgame of a doomed love situation motivated me to head out of New York to the city I used to live in, where the close-knit scene there throws an annual, woe-melting Halloween warehouse rager. The kind of party that includes a maze where if you successfully crawl through a dark tunnel lined with old cold cuts, you’re rewarded with a sledgehammer and ushered into a strobe-lit room full of old electronics. I get to the party, there’s a guy in a mask covering Seal’s “Kiss From a Rose” on a chainsaw through a distortion pedal, and people are wrestling in a net suspended 20 feet over the crowd. I’m engaged in some boring conversation about poetry when a girl I used to date interrupts to ask if I was “monogamo” and, if not, did I want to make out for “five minutes.”

Within moments of politely excusing myself from the discussion, she had pushed me up on top of an old wooden desk and was groping me while I forced her jaw open with one hand and shoved fistfuls of Laffy Taffy into it with the other. She kept asking to touch my “pajama,” she didn’t have a cool costume, and when later on I said, “If someone had mentioned to me in high school that at age 25 I’d be spending Halloween getting fingerbanged on the floor of a converted warehouse I’d have responded ‘thank god,'” she was like, “The warehouse isn’t converted.” Four days later, when the girl from New York finally called it off, it didn’t seem so bad after all, even though it meant I got dumped by someone wearing board shorts in November. What I’m trying to say is, sometimes all you need is a solid Halloween to remind you that despite all the bullshit we live in the best of all possible worlds.

Previously: Take This Halloween Costume Idea … Please.


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