Image by jastrow75, via Flickr
Allison (not her real name) and I had broken up once before, and I had been miserable. This time around, I internally promised, I’d force myself to have fun. I’d have new experiences. I gave myself a simple mantra: “Say yes to life.”
Cheryl was an actress studying in New York for the entire summer. I classify myself as a comedian, but I’m one of those comedians who also acts so that I can split the difference and feel insecure about both. We met via mutual friends in the scene that is the nebulous crossover area of the Venn diagram of these two activites, and she seemed like the type of low-key person who would be great to have a first date back in the game with. I was attracted to her. I asked her out. It was awkward. But she said yes.
She was lukewarm on the idea of going on a date with me. I figured this out when she initially stood me up. That was a real red flag for me. But she texted me that she was sorry and would still love to hang out if I could do it much later that night. I brainstormed late-night options that would show a non-New Yorker something reasonably interesting, and decided on Chinatown, which I like because it’s cheap and interesting, but also feels like someplace where you might get stabbed. It’s full of alleys and shops that sell illegal fireworks and illegal baby turtles and, in general, feels like one of the least Giuliani-fied areas of New York City still standing. It’s fascinating and gritty, and on top of all that it has fantastic food, as long as you don’t mind sitting at a table located perilously close to the dangling corpse of a recently butchered duck or a 100-gallon fish tank full of crabs who have lost all hope.
Many of these restaurants are open 24 hours, so we headed south of Canal Street in my Ford Fiesta. I was hoping we’d get to see something really outlandish, like a street fight among Triad gangsters, which sounds racist until I tell you that is something my friend Eugene actually wandered into the middle of accidentally, one night down in Chinatown, and I’ve always been jealous of him for it.
So it was a standard late-night Chinese-restaurant date. At first I thought things were going fine. Then I noticed my left arm was curled up, and it looked like I was suffering a stroke. It was only then that I realized that I was insanely nervous. My human arm had betrayed me and turned into a dinosaur arm.
Our conversation was stunted and unpleasant. This was 100 percent rooted in my marble-mouthed conversational skills. The worst it got for me was when she asked, “When you were my age, was Google even a thing?” I remembered when I was young and asked older people hurtful questions that I didn’t realize were hurtful. Worst of all, her instinct was correct—when I was 24, Google wasn’t really a thing yet. We still used Yahoo and Altavista, and even Dogpile, which was the search engine that searched all the other search engines at once since they were all so shitty. Not many people remember Dogpile. My date certainly didn’t. I talked about Dogpile for 20 minutes.
I drove her back to the West Village apartment building where she was staying, expecting an uncomfortable goodbye. Instead, she leaned over and kissed me.
I was fucking terrified.
I can’t fathom any reason why she would have made out with me besides pity. I’m not exactly Don Draper when it comes to physical attractiveness. I don’t think I’m ugly, per se, but on bad days I have been told that I look like the monster from The Hills Have Eyes. That was extremely confidence-shattering, so I try to take care of myself. When I really have it together, I think I successfully pull off looking like the exact middle point between Macklemore and Ron Howard, only with a much bigger forehead than either of them. Let’s put it this way when it comes to attracting ladies, I’m extremely lucky I’m funny. But I wasn’t being funny at all that night, so my best guess is that the level of hopelessness I was putting on display went so far to the end of the spectrum of hope that it somehow crossed over and became attractive in its own right.
Anyway, after a few minutes of car making out she whispered, “Do you want to come upstairs?”
Say yes to life, I reminded myself. Despite my internal terror, I took a deep breath and followed her into the lobby.
She paused at the elevator. “My friend has a one-bedroom apartment. We can’t fool around on her couch. She’d hear.”
“OK,” I responded. “Did you have a plan?”
“Maybe we can go hook up on the roof,” she answered.
When I was 17 years old, I got caught by an Essex County police officer performing cunnilingus on my high school girlfriend in the back seat of my mom’s Saturn in the parking lot of the South Mountain Arena in my hometown of West Orange, New Jersey. Since then, I’ve looked to keep things behind closed doors. But I stayed true to my mission statement and decided to say yes to life.
We made our way to the top floor, then headed to a stairwell, when I noticed something very weird: There was a secret floor. The stairway didn’t go straight to the roof, it had this landing, and the landing lead to a hallway with one door.
“Do you know who the only person on this floor is?” she asked.
“Now how would I know that?” I responded.
“Do you know who the character actor Alan Rickman is?”
I was stunned. Of course I know who Alan Rickman is. He’s the bad guy in Die Hard. He’s in the Harry Potter movies. And to any male of my exact age, he will forever be the sheriff of fucking Nottingham from the Kevin Costner Robin Hood movie. I think it’s dope that Alan Rickman gets to live on a secret floor in a West Village high-rise. He’s a great actor and has always struck me as a quality human being, and my initial thought on realizing that he had his own secret floor was, Good for Rickman, he deserves it.
But I digress. We made our way to the roof, and I was immediately dismayed to see that the building was not as tall as any of the buildings surrounding it. Cheryl kissed me, and I looked over her shoulder at the windows of the nearby structures, fully expecting a neighbor to look out the window, make eye contact with me, and shake her head disapprovingly.
I did have one thought that calmed me down: At least with this being semipublic, it won’t go too far.
I was wrong. It went way too far, way too fast. My shirt wound up on the ground immediately. Her shirt and bra soon followed. Within minutes of hitting the roof, I was half naked alongside a 24-year-old stranger. I realized she was the same age I was the last time I’d been single, and the thought immediately placed me deep in the most insecure regions of my brain.
The eye-level windows and my own internal panic were bad enough, but things soon went from bad to worse. Cheryl stopped, looked up at me, and quietly said, “I think you should go lean against the wall.” She nodded towards the butt-high retaining wall that encircled the roof.
“Why?” I asked.
“I think it would be a good idea for me to go down on you,” she smiled.
I know this sounds strange, but I was shaking with fear. Poor you, a 24-year-old wanted to suck your dick. I know, I know, I agree. I am the textbook “kid who grew up in the suburbs and now lives in Brooklyn and can make anything a problem in his own privileged mind.” It’s infuriating. But in that moment, I promise you it was very genuine: I wasn’t expecting any of this, and I was so, so scared.
As I leaned against the wall, I saw a flash of movement in my periphery vision and looked down to see a cop car pull onto the block and stop.
Great, I thought, he thinks I’m going to jump. He’s probably radioing for backup right now. And instead of me jumping, he’s about to see the awkward head-bobbing of a nervous 32-year-old man getting an unexpected blowjob. I’ve never been arrested before, and in a fantasy world where I’m a badass, it would be for something cooler than a “nervous outdoor blowjob.”
As Cheryl undid my pants, she asked me a question I haven’t been asked in a very long time.
“Are you clean?”
Now before I even get into it, let me say this in my preemptive defense: I didn’t know if she meant, Are you STD free? or Have you showered today? We’re in the middle of a heat wave, and it could be swampy down there.
So my response was:
“Yeah… wait, what do you mean?”
That is never the right answer to “Are you clean?” It’s bad enough to be evasive to that particular question; it’s even worse to be evasive in a way that indicates you don’t even understand the concept of cleanliness. I challenge anyone to come up with an answer to that question that drops the ball harder than mine did.
Here’s the real fucked-up part: the answer to both questions was yes. I’m STD free. I’d showered that day. I am just such a neurotic mess that I needed to know I was answering the right question even though the answer to both options was the same.
Miraculously, Cheryl proceeded. I was as far in my head as I have ever been. I was thinking about the cop car, looking in windows to see if there was eye contact to be made, beating myself up for asking, "Wait, what do you mean?" And if I’m being totally honest, I was wondering how I fucked up so bad that I went from an eight-year relationship to getting head on a roof at 3:30 AM from someone I didn’t really know.
Focus, I told myself. Let the anxieties go and just enjoy this.
I took a deep breath, centered myself, and looked straight ahead and realized I was staring into a window.
That window looked into the staircase we used to get to the roof, and it occurred to me:
If I see someone angrily stomp up those steps, I won’t see some random silhouette pass by. I will see the distinctive big nose/half mullet profile of NOTED CHARACTER ACTOR ALAN RICKMAN. That is the only person who lives on the floor underneath us. If we’re making noise, the only person on earth glancing up at his ceiling with an annoyed look on his face is the SHERIFF OF FUCKING NOTTINGHAM.
So on top of all those preexisting anxieties, I now had scenes from Robin Hood: Prince of Thieves running through my brain: specifically, that scene where Alan Rickman tells his cousin to cut out another man’s heart with a spoon. And then I started giggling, thinking about Alan Rickman catching me getting blown and threatening to carve my heart out with a spoon.
All of these anxieties were adding up fast. The cop car. The windows. Wait what do you mean? Alan Rickman… And I am 32 years old.
If some of you haven’t connected the dots I’m laying out for you, I'll just say this: the best part of losing your erection while it’s in someone else’s mouth—is no part.
Rickman never came. And neither did I.
In the end, Cheryl was very understanding. Against all odds, we saw each other a few more times. Then she headed home, away from New York. I still see her when she passes through town, and we laugh about our night spent on Alan Rickman’s roof.
My life as a single man had begun with a flaccid whisper instead of a firm, hard bang. The ball was rolling, even if the balls weren’t. I’d reentered the fast-paced, terrifying, exciting, demoralizing world of dating in New York City.
Things would get worse before they got better.
Comedian Chris Gethard used to write for Weird N.J., a magazine that chronicles the strange shit that happens up in the highlands and deep in the swamps of the Garden State. He also wrote a book of personal essays called A Bad Idea I’m About to Do. You might have seen Chris on HBO’s Bored to Death, NBC’s the Office, hosting his popular cable access show, “The Chris Gethard Show,” and other venues of high repute. We decided it’d be a good idea for him to tell us some stories about being newly single and vaguely famous in NYC.