Flavor of the Week: Love Don’t Cost A Thing
My senior year of high school I found myself, in-between long bouts of doing nothing and hours spent trawling the Internet for new music, with a girlfriend named Melissa. She was an Ivybound overachiever with a clear sense of direction and a thing for singer-songwriter stuff. I was a kid who didn’t know what a GPA was until I was 16, when I learned that mine was absolutely terrible. Because I was (and remain) a deeply, deeply silly man, I was the only kid in town who never learned how to drive; because she was a year younger than me, she could not legally operate a vehicle. Which is what led to a whole lot of hyper-emasculating car rides in the backseat of her mother’s car.
For example, on the morning of this story, her mother drove us to the train station. I grew up on Long Island, and like most other Long Island teenagers, saw “The City” primarily as a place to spend way too much money at the one sake bar that didn’t card.
We were set to go into Manhattan to dine at some sort of fancy, chocolatethemed restaurant, where presumably I would take out the wallet that I still don’t own (I’m a loose bills kind of guy) and pay for our meal. Being a proud member of what certain sociologists have termed The Hook-Up Generation, I had never taken a girl out on a proper date before; since that evening, I have gone to strenuous lengths to avoid ever doing so again. (“Are you sure you don’t just want to come over and watch a movie for free? No? How about a bike ride?”) The day had been going all right before we got to the restaurant, although dread over how I’d be able to pay for the eventual meal sort of killed the mood on our trip to the Museum of Television and Radio. (She was doing research for a class; I was watching old episodes of My So- Called Life and struggling to see what all the fuss was about.) We’d lost our virginity to each other a couple of days earlier, but when I tried holding her hand on the sidewalk, she did not seem very interested.
At the restaurant, where gilded decor did not bode well for my eventual checkpaying prospects, we were seated behind a couple that seemed to be roughly our age. I don’t remember exactly what they looked like, but I do recall thinking them a better adjusted, more attractive and generally cooler version of me and Melissa. (This probably had no basis in reality; I am nothing if not insane.) The waiter came, and Melissa began ordering without discretion, bringing to our table all sorts of expensive chocolate delicacies: chocolate waffles, chocolate fondue, chocolate crepes. At any point I could have said, “Hey, just a warning, I cannot afford all of that stuff, are you OK with splitting the bill, or perhaps holding off on the Chocolate Chunks Pizza?” to which she would have most likely responded, “Either of those options sounds completely reasonable!” But instead I started waving around the fire sticks that came with our chocolate s’mores while openly leering at the couple that had probably discussed payment plans beforehand.
I should note, here, the sad circumstances of our courtship. She had had a crush on my best friend, who, after a years-long struggle with acne, had emerged as an enviably handsome guy. I had had a crush on her dumber, prettier friend. So when these two more attractive friends inevitably got together, what else were we going to do but stare at each other unhappily over expensive chocolate delicacies?
And then the check came, and I couldn’t pay for it. “We could have just gotten hot dogs on the street,” she said, sadly.
On the brisk walk to the train station I kept stopping to apologize and maybe kiss her, but she did not welcome any of it. I don’t remember exactly what she said to me, but it certainly was not a warm, “It’s OK, don’t worry about it.”
Her mom came to pick us up at the Long Island train station and drove us to our friend’s house, where I got drunk, hit my head on a too-low basement ceiling and ended up crying while sitting in her lap—not because of the ceiling thing, but that certainly hurt, too. We broke up two days later. These days she goes to Yale and interns at Goldman Sachs, and I eat street hot dogs regularly.

