The most successful Halloween costumes are classic but topical, sexy but funny, not too ugly and not too obscure, perfect conversation starters and ideal photo-ops. I am not telling you this because I am a Halloween genius with wisdom to spare. I am telling you this because I have spent 29 years failing at Halloween. I have never been cooed at, kissed, or celebrated for my wit and style on Halloween. In fact, each Halloween has been more demoralizing than the last. Men have it real easy in the Halloween department. They can wear a beer helmet or a rubber Nixon mask and call it a fucking day. While women are meant to be both transformed and adorable, a near-impossible combo for most of us, men can use Halloween as an excuse to let their guts hang out and be celebrated for it. But the standards for women are Harvard-admissions level, even harder if you're single and need to factor in something with a snap crotch. My lack of Halloween success started early. When I was four, I told my parents I wanted to be a mermaid-fairy for the Washington Market Park Halloween Parade, and this is what they came up with.
My dad sewed this mer-tail all by himself, which is incredibly sweet, but the fact that the tail emerged from my butt rather than wrapping around my legs left a lot of people confused. That, coupled with the ratty wig, made me look like this homeless rave person who once wandered into our elevator in the '80s demanding juice.
The next year, I decided to go as a "fancy lady." To me, this meant a Miss Havisham/Grey Gardens hot mess, fallen from grace but clinging to her evening gloves. The wig being askew was a definite choice. I went home early, weeping, after this rude bully called Peter N. told me "Fancy lady isn't even a real costume."
In 1993 I decided to own my power and go as Medusa. My mom went to the hobby store and bought me a bunch of plastic snakes that she super-glued to my leotard. As they started to fall off, so did my spirit. I lost my snakes all along lower Broadway, and with them a little piece of myself.
I spent the entire next year planning this secretary costume. I was really obsessed with Nick at Night, and secretaries were always running in and out of those vintage sitcoms with something important to say. "Mr. Grant, there's an urgent call!" My cousin Julie was a vampire and really stole the show. I think I looked way too much like a teensy alcoholic divorcée to be a good candidate for candy.
The year I went as a leopard was the year I sold out. I remember feeling like I'd really let my heart be polluted by the darkness. Everything about this look felt stupid and basic and sad. I didn't get any more compliments than usual, because I didn't have the frisky spirit of Kendra, who was dressed as a bat, or Bo-Ram, who was covered in purple balloons to mimic a charming bunch of grapes. I was normal, and no one gave a shit. I skipped the party in the school gym and the next day walked around my living room dressed as a fortune teller for an audience of no one.
As a teenager, I didn't really dress up because I didn't have anyone to dress up with. I was terrified of drugs, alcohol, and socializing, and I didn't share an aesthetic or sense of humor with anyone really, which is essential for Halloween enjoyment. But freshman year of college, my whole dorm got dolled up and we hit the West Village Halloween parade. I went as a mermaid, this time in a store-bought costume made of itchy sparkly rayon rather than an ass-tail made by my dad. I was pretty sure this look would lead to the loss of my virginity, but mermaids don't have vaginas, and painting my face blue was perhaps a bridge too far.
The next year, I went as a "showgirl," and I'm pretty sure I made out with an electronic musician in the dirt under a porch in Ohio. I awoke smeared with mud, all my fake nails stuck to my face and body. I had mono.
The last time I dressed up for Halloween was in 2011, when I went as Louis CK. It was my first year "in the film industry," and the party I was going to seemed very elite and intimidating. It was full of male comedy writers, a subgroup I no longer get quite so hot and bothered by, but at the time, I considered them the height of marriage goals. I thought my Louis costume would immediately establish me as cool, fun, and in on the joke. Plus, this was Hollywood — wasn't everyone too sophisticated to fall for yet another sexy cat??
The answer to that question is no.
As I approached the party, I saw a group of scantily clad gypsies smoking with a Tony Montana. By the bar, hot race-car drivers in skintight suits and hair extensions knocked back shots. A few feet past that, a sexy Steve Jobs with a white turtleneck and an Apple tramp stamp was chatting with an Axl Rose (actually, kudos to Jobs). My goatee felt hot and heavy on my face as the room started to bend and blur, and I headed toward the bathroom, only to be intercepted by an ex-boyfriend and his current flame dressed as "French Kiss" (this involves KISS makeup, baguettes, and me contemplating suicide). I saw an acquaintance and ran toward him, wrapping my arms around his neck: "Oh, thank G-d!"
He flinched. "Do I know you?"
"It's me, Lena!"
"Oh, Jesus, I thought you were a very short computer programmer from the Valley."
It only got worse from there, when a drunken starlet dressed as, you guessed it, a cat asked me what I was meant to be.
"I am Louis CK."
"An acclaimed American comedian. He's really funny. He has red hair and —"
"Oh, wow!" she squealed. "You even did padding and everything!" After which she proceeded to pinch my actual stomach flesh. Hard.
"That's my real body," I whispered. And with that, I removed my bald cap and headed home.
I was recently telling this story to my friend Sarah Sophie Flicker, framing it as part of the larger Halloween struggle, when she said something remarkable. Sarah, a glorious eccentric with a penchant for Victorian dresses and dramatic headpieces, told me: "Halloween is for amateurs." Halloween, she argued, was a day for terrified people who otherwise live a life of polo shirts, Dockers, and sneaker-bottom loafers to finally let their freak flags fly. "Every day is Halloween for me."
And she has a point. If I want to dress like a suburban boy on a European teen tour to go to the grocery store, I do it. If I want to let my kimono drag across the floor while I pour Whispering Angel rosé into a Chelsea Lately mug, that, too, is my prerogative. With every outfit I evoke a character, even if that character is a pro golfer named Jan who wears a fleece vest and orders three hot dogs at the movies. I spend the entire year occupying my arsenal of freak people. Some are sexy in a way that translates in a dark bar. Some make people cross the street. Others are known only to me as I skitter around the house at night in a Bermuda-tourism T-shirt. But my characters need to bust out 365 days a year, not just on Oct 31.
Still, I want to be accepted and to WIN BIG! And this year, I think I may have finally nailed it. I'm going as something newsy, sexy, and cool: a Planned Parenthood doctor!
And please remember to imbibe safely, avoid unwrapped candies, and never let a sexy cat pinch your stomach flesh.