A Few of My More Humiliating First Date Mishaps
It was horror movie night at the enormous, dilapidated artists’ hovel she shared with eight housemates in West Oakland. For obvious reasons, I did not reveal the fact that I was/am absolutely terrified of even the tamest scary movies. (In fourth grade, I watched The Sixth Sense at a friend’s house and slept with the lights on for the next six months. My parents never forgave him.)
We watched The Babadook on a blurry projector, the eight housemates scattered around the room like discarded laundry. I cuddled with her on the couch, positioning myself behind her so she wouldn’t see that I had my eyes closed for half the movie. Afterwards, I stayed over—and alarmed us both in the middle of the night when I woke, very obviously from a nightmare, screaming and thrashing and drenched in sweat. We did end up going out a few more times after that, but I don’t think she ever looked at me quite the same way again.
She’d been my girlfriend for almost a month, but we had yet to go on an actual date, because that’s how things worked in eighth grade—our “courtship,” if you could call it that, had been conducted entirely over AOL Instant Messenger. But that afternoon, after school, it was finally happening: a trip to the ice cream shop.
She knew that I had never kissed a girl before, so in advance of our date, she sent me a link to a website called “How to Kiss,” with illustrated, step-by-step instructions. From the middle school computer lab, a friend and I scrutinized each pixel of this website with the intensity of someone studying the Zapruder film. Nonetheless—and with no disrespect intended to the creators of the sadly now defunct HowToKiss.net—it would be several more years before I successfully learned how to kiss.
We matched on Tinder. The plan was to meet at my place for a quick drink, then head to a concert.
My place, at the time, was a formerly-abandoned mansion in Detroit that some friends and I had purchased at auction and were in the process of renovating. I’d mentioned this to her, but I’d probably failed to sufficiently emphasize just how decrepit the house still looked from the outside. When she pulled up, she was too creeped out to come in, so she made me talk on the phone with her for thirty minutes, while she sat in her car outside, to prove I wasn’t a serial killer.
She told me her type was “spicy whites”—Italians, Greeks, Jews, etc. Later, I met her high school boyfriend, and he looked unnervingly like me.
During a quiet moment in bed, she asked me what I was thinking about. An ex had gotten mad at me for always replying to that question with “nothing,” so I decided—stupidly—to be honest. I said, “I’m thinking about how weird it is that most of the Muppets have actual names, but Big Bird’s name is just a description.”
After a few drinks, she explained that she “couldn’t decide” whether or not she was attracted to me, and asked that we extend our date so she could take some more time to think about it. Two drinks later, she still hadn’t reached a definitive conclusion, so I got bored and went home. I assumed I’d never hear from her again, but a couple days later she texted to say she’d that given it some more thought and could now confirm that she definitely wasn’t attracted to me. I couldn’t decide if I was stung by her disinterest or flattered that she’d devoted so much time to considering the matter.
A couple years after we hooked up, she published a memoir about the men she’d encountered in the New York dating scene. It was called Bad Sex.
It was fall 2020. The plan was to meet at a combination coffee shop/wine bar, grab some drinks to go, and head to the park. When I arrived, she was already inside, aimlessly browsing, and I started chatting her up. She was a little standoffish, but I didn’t think much of it—Covid had made us all forget how to socialize normally. After a few minutes of stilted conversation, I suggested that we order our drinks and head out. She looked at me like I’d just suggested we go lick the subway pole.
That’s when the little bell above the front door jingled and my actual date walked in. I had been talking to a stranger who just looked a lot like my date with her mask on.
She told me I came across as arrogant and obnoxious. Nonetheless, we got married a year later.