The greatest Halloween hook-up story ever told


I walked into the bar without much expectation, just as I had so often that semester — the first half of which had been speckled by moods that ranged from “sad” to “hopeless” to “sad and also pretty hopeless to the point I’m guzzling Mad Dog on a Tuesday afternoon,” all painted over a frame built of unrelenting celibacy.

I was in a bad way, I guess. I had lost all confidence, all vague assurance that somewhere there was an attractive woman who wanted to spend time with the likes of me.

Lofty mating expectations were particularly unreasonable for me on this night, dressed as I was: a human American flag with exposed white thighs and a poor excuse for a mustache. I expected nothing more than a serious binge that would see me heading home to finish a few episodes of Friday Night Lights before knocking out one more big gulp of scotch, so that I could fall into a fitful sleep where my last thoughts were self-pitying ones.

But if you expect nothing, you’re unlikely to be disappointed.

Five months earlier, my girlfriend had told me that she hoped I would die.

Five minutes after that, we broke up.

It was my first experience with real heartbreak, and afterward my confidence rivaled that of a flat-chested freshman at her first high school pool party. I spent much of the semester drinking in the dark, listening to Bright Eyes and cowering from any hint of romantic interaction.

By mid-October, I had still not gotten over the break-up. It was during this time that I found out my now ex-girlfriend had cheated on me in the middle of our relationship. With a semi-famous Miami-based tattoo artist. (Fuck spring break, amirite?)

A mutual friend referred to the dalliance in casual conversation. When she registered the horror on my face she gasped and said, “Ohmygod you didn’t know?”

If you’ve never experienced what it feels like to suddenly become aware that some other man has been inside your girlfriend and you didn’t know it until half a year later, after you’d spent at least thirty seconds at a time on dozens of occasions doing the same, well, then I hope you never do. Because it really fucking sucks.

I was uncharacteristically unenthused about Halloween that year. I’d spent time brainstorming costume ideas, but had sprung into action too late to make any of them happen.

So I ended up leaving the house in a royal blue track jacket with a white V-neck underneath, a white bandana wrapped Rambo-style around my head, and crew socks. The sexiest part of the outfit was a pair of red shorts that I affectionately refer to as The Plum Smugglers. (Had my father passed unto me anything more than a medium length jawn, a wardrobe malfunction would have been imminent.)

My marathon-running brother, provider of the outfit, had suggested we go to a bar where a girl he liked was headed with pals of her own. (Fun fact: the girl he liked is now his wife.)

“It’s the day before Halloween,” Kev said. “So the odds are in your favor. The holiday, it brings out the inner trollop. You’ll see.”

“Right!” a friend said. “And the best way to get over someone is to get inside someone else!”

I nodded, for his benefit.

On our way downtown, Kev and I broke into a light jog, taking turns handing off a ShakeWeight we hoped would resemble a relay baton. Fellow revelers gleefully greeted us with fist bumps and Forrest Gump references. I tried to affect a similar level of enthusiasm, but most of my thoughts were, disappointingly, about my ex-girlfriend. One friend joked that she was probably dressed as Kat Von D, and I laughed, trying to seem unfazed, while inwardly I was banging my head on a wall and repeatedly screaming things that the lead singer of Staind probably often says aloud.

Things like, “What in the fuck did I do to deserve this fucking shit?”

Kev’s girlfriend and her friends arrived while we were drinking on the back patio, and my brother pushed me toward a brunette I assumed was supposed to be Gerard Butler’s wife from 300.

It was Chelsea, a pretty girl I’d met briefly at a party earlier in the year. That time, we’d spoken only for a few moments, probably because I had plans to go home soon to my bedroom, so that I could cry in bed while watching speeches from romantic films on YouTube.

I waved rapidly (and awkwardly) when she was two feet away, because I’m not cool enough to pull off a non-creepy head nod.

Eventually (because liquor) I forgot that the lower half of my body was even more exposed than hers. And pretty soon after (because liquor), I forgot that I was still reeling from my first cuckolding. I quit thinking entirely, really (because liquor); I’d even absentmindedly put one of my old-school Nikes up on a chair and was rocking back and forth as I spoke with her, like I was Captain Morgan in the Olympic Village.

She didn’t leave my side for any of the other guys at the bar — which a woman of her caliber could have easily done — and an old friend, Optimism, poked its head around the corner and gave me a head nod. My confidence was building. I head-nodded back.

Who knew? Maybe I’d get Chelsea’s number at the end of the night. I’d start texting and researching on Facebook until I knew every single thing about her, and then I’d ask her to spend time with me again in person.

Sometime around midnight, one of the girls vomited in the middle of the bar and my brother started barking in a made-up language that sounded like the one we’d used as children to make pretend communication between our stuffed animals. It was time to leave. We headed toward my apartment to post-game.

On the way, Chelsea pulled me aside when we were near her building.

“I need to grab something. Want to come up with me?”

Either this something was heavy and she needed help, or I had just been invited to do the sex (or something a few bases before home) with a woman for the first time in months.

My scarlet shorts quickly became a miniature Red Cross relief tent and I said, “Sure,” all nonchalant and shit.

Kev heard the exchange and ran up to me to slap a double high-five before sprinting down the street screaming, “Yeeaaaaahhhhhh!”

We traipsed up Chelsea’s stairwell and into her apartment, where she introduced me to her roommates and then whisked me away to her room where we commenced a heavy make-out session. My main concern was that a recent lack of use would reflect poorly on my longevity. I did not want to embarrass myself with a six-pump dump.

But then another source of anxiety presented itself.

She was down to her underwear and I was down to my crew socks and bandanna when she asked if I had a condom.

always carried one in my wallet. Since I was, like, 13. (I wasn’t kidding when I said that Optimism was an old friend.)

But because I’d had no place to put it, I’d left that all-important leather rectangle and its — at the moment — most vital component at my home. I’d taken out my debit card and driver’s license and stuffed them into my socks.

I thought about my options. Two-point-five seconds later I made a cheercision: I was going to be a fucking champion that night, whatever it took.

“Don’t move,” I said. “I’ll be right back. Seriously; stay just like that.”

I dressed and sprinted down the eight flights and outside to the bodega next to her apartment. It was closed, but I was not to be denied. I began running down one of Penn State’s main streets in the direction of an all-night convenience store I knew was only six blocks away.

A group of frat dudes began a “USA!” chant as I passed them.

Inside the store, I grabbed a three-pack and threw it on the counter, holding out my debit card with one hand and wiping sweat off my brow with the other.

The cashier pointed to a sign indicating I had to meet a $10 limit to use the plastic. I guess I could’ve purchased some lube, or maybe a Gatorade, but tunnel vision led me straight back to the rubber rack, where I snagged three more three-bangers.

I was taking too long, I thought as I checked out. Chelsea would probably be asleep when I returned and fail to buzz me in. Or she would allow me in for a passionate cuddling session, at best. Eventually, she would fall asleep and I would retreat to her bathroom where I would weep, snap one off, or both simultaneously.

So I ran out of the store and up the street.

As I hit my stride, I realize I was on my way to a woman’s apartment with four boxes of condoms.

What was I going to do? Bring them back and explain what had happened? Chelsea might find it vaguely romantic, but she might also assume I was being overzealous — that I was planning some sort of sexual marathon. (See what I did there? You know, because of my costume?)

I was ready to toss most of them in a trashcan when I saw a Fireman with a Flo from the Progressive Insurance Ads. I handed the guy a box and muttered something about points for safety. I handed another to a Spider-Man (“for web-slinging!”) and one to a UPS Man (“special delivery!”) before I finally arrived at Chelsea’s.

She buzzed me in. Her mood, like mine, had not dissipated. We got right back into it.

When we were done — after more than six pumps (because liquor) — I went to the restroom, looked at myself in the mirror, and thought briefly about high-fiving my reflection. Then I returned to the bedroom, where I grabbed my phone out of my sock to check it before snuggling up next to Chelsea.

A friend was back at my place, very drunk and very sad, with a broken heart he’d sustained more recently than I’d sustained mine. He’d called and texted a few times, wanting one of our empathetic late-night balcony conversations to help set his mind right.

“Go!” Chelsea urged me when I explained the situation.

So I did.

I walked into the street, tied my shoes and stood pretty tall for a few seconds. It was the first time in a long time that I wasn’t so sad.I took a deep breath, texted my friend, and told him I’d be over soon. I’d tell him that Kev’s friend had been right, in his fratty way: the best way to get over someone was to get inside someone else, even if that’s only a momentary fix.“We’ll figure it out,” I wrote. “It’s Halloween. The odds are in your favor.”

I tucked my phone into my sock. I smoothed the wispy mustached I’d crafted earlier.

And then I ran all the way home.

On the way, I caught a glimpse of my reflection in the floor-to-ceiling windows of a Bank of America. I slowed and realized that, for one night at least, I’d left myself behind. I’d become someone else — someone who wasn’t sad, who won more than he lost, and had a mustache and short shorts and hairy white legs.

I’d become the man Kev and I had tried to emulate back at the house:

Steve Prefontaine.

Runner. Lover. And greatest Halloween costume I will ever have.

As I write this, I am wearing a long-sleeve green T-shirt I’ve had since high school. The yellow print on it reads:

“Pre Lives.”

Fucking right he does.

This article originally appeared on Medium
Title Photo Credit: flickr