But it was clear she had other ideas—and rightfully so. We’d been making out and groping for weeks, and it was natural to think that things would progress. She didn’t know I was a terrified little boy who still lived in the suburbs. Lisa was going for...
Photo via Wikimedia Commons
I am not good at hooking up with people in New York City.
Let’s review some facts about NYC. Bars don’t close until four in the morning. Public transportation runs 24-hours a day. If you’re in a situation where you need to get home immediately, cabs drive by and slow down just in case you’re in the mood to get a ride. If no official cabs are available, there are countless 24-hour car services you can call that will send a car to you in a moment’s notice. And most of the young single people live in one of about a dozen neighborhoods. It’s a city built for horny people to get drunk and go home irresponsibly with one another.
There are also well known places one can go to wind up in relationships of varying seriousness. For example, the ZogSports kickball league is a notorious matchmaking service disguised as a hipster sporting event. No one joins ZogSports kickball because they like kickball, they join it because they want to find someone to make out with who is mildly athletic and into irony. And a lot of bars are notorious for being the “if you’re still here after three in the morning, you’re clearly trying to hook up” variety. One of these is Union Pool in Williamsburg. I actually kissed my current girlfriend for the first time at Union Pool, leading my friend Laura Stevenson of the fantastic band Laura Stevenson and the Cans to tell me “You’re the first person I’ve ever met who made out with someone at Union Pool and actually talked to them afterwards.”
Hooking up in New York means many things to many people. It moves quick, has its own built in rules, and like anything else in New York City, it does not slow down so you can get used to how it works.
I didn’t have much experience hanging out in New York by the time I was in college.
In 2002, I was taking an improv class, because as a white male with glasses who was born between 1978 and 1994, it’s legally required that I take at least one improv class in my life. There was a girl in that class who thought I was funny, and she was flirting with me to a degree that even I couldn’t miss it. I’ve always been oblivious to girls liking me. This is because for most of my life they didn’t. Also, I wasn’t hip enough to know that at a certain age there was the potential for a “why is Woody Allen appealing?” type of charm to hit for a guy of my type. But with Lisa, there was no missing it. She was into me. She’d wait after class with big doe eyes blinking at me, saying sweet nothings like:
“How’d you get so good at improv? The thing where you pretended to be the salami was sooooo funny.”
Then she’d touch my arm and giggle, and I would also pretend that me pretending to be a salami was funny. After a few weeks of this, I asked her to hang out and we did. We had fun together.
I still lived in New Brunswick, NJ and attended Rutgers University – a magical land where sofas get burned in random locations and you never know when a coach might bounce a piece of sporting equipment off your dome. Lisa lived in Astoria, Queens, a magical land where your Greek landlord might raise your rent at any given moment. So we’d meet in the middle, Manhattan. We’d get food or drink, and then invariably end up making out on random front stoops. This would usually happen on the west side in Chelsea, because I was constantly nervous I would miss the last train home to Jersey and was scared to venture outside of a 12 block radius surrounding Penn Station.
The physical expressions of our young love were unfolding on the front steps of brownstones owned by gay men throughout the greater Chelsea area, so nothing went too far. In the first three weeks of our courtship, I’d felt her boob over her shirt and she’d rubbed my wiener through my pants a few times. We’d make out for hours, then I’d glance at the time and frantically sprint to Penn Station. She must have thought I was the biggest male tease of all time. She was rubbing my boner, and I’d get up and run away each time. She must have been wondering what my deal was – was I playing hard to get? Did I enjoy sitting blue-balled for an entire 90-minute train ride?
The hard-to-get factor must have worked, because before our fourth weekend together she called me and asked me something very simple:
“Do you want to come over and watch a movie this weekend?”
Now again, I want to return to the topic of New York hook-up codes. Like I said above, kickball ain’t always kickball and some bars are better for making out than others. There are just certain things everyone dating in New York City knows. I don’t always know these things. I’m a dummy from New Jersey.
Here are two things that I know to be fact after dating in New York for as long as I have. The second one applies to our story. The first is just a friendly tip for anyone else who is currently young, naïve, and new in town, as I once was:
1) If you are on a date with someone and they say the words “I was raised in Manhattan,” they’re telling you that they were more sexually liberated by their sophomore year of high school than you will be in your entire life. If you’re a heterosexual man in this situation, do not feel bashful if a girl of this type puts the moves on you—kids who were raised in Manhattan have the sexual adventurousness of Parisian flappers circa the roaring 20s. (Again, this has no application to the rest of this particular story, but it’s very much worth knowing if you want to date in this metropolis.)
2) If you are dating someone in New York City and they invite you over to watch a movie, they don’t really want to watch a movie. According to Google, there are over 250 movie theaters in Manhattan alone. You can see blockbusters, documentaries, artsy films, old films, foreign films, any kind of film in New York City, at all hours of the night. No one in New York hangs out in their apartments. If you’ve been making out with someone and they say they want to watch a movie and the location for said event is a private home and not a movie theater, they plan on fucking, not movie spectating. The movie is the painless excuse to get inside, where the fucking will happen.
I was not aware of this rule.
Photo via Wikimedia Commons
I’d never been to Astoria before visiting Lisa’s house. I drove out, parked, and made my way to her front door. She ran down to let me in and grabbed me with the furious intensity of someone who’s spent the past month dry humping on stoops every weekend night. She threw me against the wall in her staircase and made out with me. Lisa was feeling passionate. I was somehow surprised.
We made our way upstairs and sat in her living room for a few minutes. She told me we’d watch the movie in her room. I poked my head into her room.
“The TV in here is so much smaller,” I said.
“So?” she answered.
“If we’re going to watch a movie, shouldn’t we watch on the big TV?”
She giggled, knowingly. As if I was kidding. As if we were in on the same joke. I wasn’t.
“I got a copy of All About Eve,” she said.
“I’ve never heard of it,” I answered.
“It’s got Bette Davis,” she said. “It’s a classic.”
“Oh cool,” I answered. “I’ve never seen anything with her. This should be fun.”
Lisa again giggled, as if we were on the same page. We weren’t. She thought I was playing along. I wasn’t. I was really interested in Bette Davis.
Years later, my friend John told me about his role in this date. He and I hadn’t become friends yet, but he knew Lisa. John is an out-and-proud gay man, and a good friend of mine for life. Lisa apparently pulled him aside before our date and asked –
“What’s a movie a straight guy would have absolutely zero interest in?”
To which he replied “All About Eve” with no hesitation. This entire date had been set up for me to head over to the home of the girl I’d been making out with, under the false pretense of an intentionally uninteresting-to-me movie, so we could have sex for the first time with as little stressful planning and verbal recognizing of impending sex as possible. But I was too dense to get it.
We made our way to the bedroom and Lisa threw on the black and white tale of an aging theater actress and her circle of friends. Lisa started kissing my neck. I kept watching the movie. She put her hand up the front of my shirt. I kept watching the movie. She put her hand on my leg—I got sort of annoyed that she wasn’t letting me watch the movie, since wasn’t the whole point of me coming over to watch this movie?
That’s when it dawned on me: we weren’t supposed to be watching this movie. Only after a woman simultaneously sucked on my neck, rubbed my chest and teased her hand up my thigh did it occur to me that this was about something else.
I hadn’t been expecting sex. Not that night, and maybe not with Lisa ever. I was up to that point a boy from the suburbs who had only had sex with his high school sweetheart. Making out was fun, but I wasn’t sure sex was on the table for me at this time and with this other human being.
But it was clear she had other ideas—and rightfully so. We’d been making out and groping for weeks, and it was natural to think that things would progress. She didn’t know I was a terrified little boy who still lived in the suburbs. Lisa was going for it—clothes came off, mouths touched places, noises were involuntarily made.
The moment of truth was upon us. I hovered over Lisa. She reached to a drawer next to her bed and removed a condom. I hesitated. She stared at me, annoyed.
“I think maybe we’re moving too fast,” I said.
Lisa narrowed her eyes. In hindsight, I recognize that she’d had enough. She felt like I was playing games and was drawing a line in the sand. She stared me down.
“What kind of man says that?”
No sentence will get a guy to stop on a dime and reconsider his behavior quicker than a naked woman looking him in the eye and asking, “What kind of man says that?”
I’d expected a conversation. Maybe some quiet contemplation. Instead, a gauntlet got thrown and the options Lisa laid out were clear: Be a man and fuck me or Run back to Penn Station again, pussy.
I hurriedly unrolled the condom, feeling like my very manhood was at stake in the process. I was sweating, unsure of why I was doing what I was doing, and acting completely on frantic instinct.
I entered Lisa. She looked at me and I remembered immediately that I have no poker face. Her reaction to me was one of dread. I could almost hear her thinking Am I date raping a boy? Is that possible? I did my best to show her what kind of man I was, and with awkward gusto plowed forward into the act. I was shaken, nervous, my motivation all driven by the protection of my own ego and not actual desire or comfort with the situation.
It was truly sad sex. Her bed was just a mattress on the floor. She laid on her back and I pitifully pumped away at her. There was intense discomfort on both sides: hers coming from realizing she peer-pressured a guy into having sex, mine coming via the desperate and quickly unsuccessful efforts to prove my manhood. I was making shitty little panting noises, weaselly ones, as I shut my eyes and focused on the task at hand. She was completely silent.
And then, the condom broke.
I did what anyone would do if their condom broke in that sad, tense, sexual situation:
I pulled out, whimpered the words “Why are we even doing this?” and started gently weeping.
It was the first time I cried during sex. It would not be the last.
Lisa and I broke up the next weekend. It was pretty clear she felt bad, and it was very clear that my confidence was shattered. We broke up in Washington Square Park, right next to the fountain. Sadly, it was the most romantic thing we’d ever done.
Previously - Losing It on Alan Rickman's Roof