This Drunken Life: First Date

This Drunken Life is a weekly series of stories that chronicle the strange and wonderful things that can happen while out drinking.

The Year: 2008
The Place: Manhattan
The Drink: Beer

Back in ’08, I decided to cross into the forbidden frontier of online dating. I’d recently ended an eighteen month long relationship and returned to New York City after spending the better part of a decade in Rochester and then Japan. I wasn’t just interested in meeting people, but also in understanding how people met each other in a place as exclusively-inclusive as NYC.

The first girl I ever met up with — for anonymity’s sake let’s call her S — was from Nerve, a dating website with a penchant for attracting, shall we say, interesting folk (though to be honest they were far more interesting than most people I’d go on to meet at She suggested we meet up at Rudy’s Bar & Grill in Hell Kitchen. How romantic.

We also agreed that we’d hang out until 9pm and then go off to meet up with other friends. If we enjoyed ourselves, we’d meet up again later. This was perhaps the most sensible thing I ever managed to plan while online dating and, naturally, I never did it again.

So we met at the sawdust-littered Rudy’s and sat at the bar, drinking cheap beer and eating fries. S told me she worked as a “virtual designer” for a large media company.

“What exactly is that?” I asked, trying to be as open-minded and engaged as my nervous brain could muster.

“I work on a virtual re-creation of the Lower East Side. We plan concerts and stuff, using real bands who are there while their music plays, and then people show up in our make-believe LES to attend.”

“Wow,” I managed, genuinely curious. Even though I regarded myself as something of an internet geek, I’d never heard of anything like this. “Must be pretty great to get to write off going drinking there as a business expense huh?”

“I hate the Lower East Side,” she said, without a shred if irony.

To S’s credit, she was a mostly polite girl with some very strong opinions and a propensity for five-syllable frankencurses. Our date quickly became a snarkfest, with each of us taking turns with our respective rants like players in some sarcastic version of Shakespeare. While I certainly didn’t mind, this was also a tad different from the date I’d envisioned.

9pm rolled around and we parted ways. About half an hour later, at a late dinner with a friend, S texted me, asking if I’d like to join her and her friend at some random haunt in, of course, the Lower East Side. Sure, why not.

By the time we arrived, I tried to do the hazy math on how many drinks I’d already had for the night. Lots’o beer at Rudy’s and god knows what at dinner probably left me four or five in and once inside our new-found hangout, that number only rose. S introduced me to her friend, a fashion trend forecaster who was dressed like Inspector Gadget. I could not resist asking him what trends he saw coming up.

“Oh, absolutely it’s going to be Where’s Waldo. You’re going to see stripes everywhere. Every. Where.”

I nodded profoundly, as if he’d just revealed the inevitable answer to life’s greatest mysteries. I also tried to gauge this prediction against the fact that he’d ordered round after round of Grolsch Beer for the table, without asking. Before I could decide if I should be buying Grolsch stock he quickly added:

“But you won’t see it happen for, like, two years.”

I told him I’d look forward to it. Meanwhile, my friend stealthily slipped away back home and S cornered me with a drunken inquisition.

“Why haven’t you made a move on me?”

I blinked, dumbfounded. Why hadn’t I made a move? S was certainly interested in me and after all, we were on a date. That’s what’s supposed to happen on a date, right?

“I don’t know,” I admitted. “I just… don’t think I’m that sort of guy.”

This seemed to confuse her more than anything, but it was true — there was simply something hardwired into me that said you have to build up a relationship with someone before you go pawing at their body.

S and I never had a second date, but later on in that year of online dating madness I’d eventually learn that I was very very wrong about what sort of guy I was.

But that’s a story for another day.


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