I was lonely and unhappy as a teenager in Houston, negotiating both my parents’ recent divorce and my dad’s ongoing drinking problem, and I cultivated a strong desire to be sent away to boarding school on the east coast. My mother’s family was from New York, and we visited the city often, and I liked it there and was convinced my life would be better, in just about every measurable way, if I were allowed to fly the coop. I was also highly influenced by The Official Preppy Handbook, which I employed more as a lifestyle guide than the satire it was intended to be. I was 16 years old and highly suggestible.
One obstacle to my plan: I was a terrible student, particularly awful at math, and the odds of me getting into a really good school were slim to nonexistent. So my mother and I flew to Boston over a school holiday, where I was evaluated by experts at an educational consulting service. I was administered a battery of tests, and the experts determined that, in addition to other findings and despite my desperately bad math skills, I was actually smart.
This was news to me, and to everyone else too, I believe. I hadn’t said or done much to distinguish myself in the intelligence department up until that point. It wasn’t necessarily cool in Houston in those years to be an outright bad student like I was, but it was maybe even worse to be regarded as a girl who tried too hard to be smart.
The people at the educational consulting service recommended a number of schools for me to visit—not top-tier institutions by any estimation, or even second-tier, but decent enough. The type of places, I would later come to understand, where you ended up if you got kicked out of Andover, and then kicked out of Deerfield after that. Even still, I was told I would most likely have to repeat my sophomore year, as I was nowhere near ready to come up against the all-important junior year, with SATs and all the rest. I surprised myself by being fine with that.
Before heading up to New England to visit schools, we went to New York City to visit family. We stayed with my great aunt Mickey and my great uncle Norman at their Fifth Avenue duplex across from the park. It was the first New York City apartment where I spent any real time, and I just assumed, in that stupid way young people can, that were I to live in New York, it would be in a place just like this.
Mickey had a friend, Renee, who had a nephew my age named David, and they had already determined there would be a fix-up. I was excited and nervous—I was actually kind of pretty, but very unpopular with the boys I knew in Houston, who preferred something in a blonde, Baptist cheerleader.
This David went to a private boys’ school in Manhattan and lived near Mickey and Norman. Despite my nervousness and high hopes, I assumed David would be undesirable in some meaningful ways. I did not have much experience with boys, and most of what I did have had been pretty disappointing. But when I went to go meet him in my great aunt’s lobby at the appointed hour, I was shocked. He was very attractive—tall, with a spray of freckles, strawberry blonde hair and blue eyes—and way, way out of my league, at least by Houston standards.
He took me to Dorrian’s Red Hand on Second Avenue, where he seemed to know the bartender and we didn’t get carded. There were a lot of kids our age there, and they all—but the girls especially—struck me as deeply sophisticated, older than me somehow even though we were probably the same age. I recognized one of them as a model I’d seen in Seventeen. David ordered a beer and was served one. I ordered a screwdriver, the only drink I really knew how to order, and sipped it slowly. The taste of alcohol was still pretty gross to me.
I do remember thinking after a while that David seemed like kind of a dick. He bragged a lot about his dad, who was apparently very important in the music business, and then made a mean joke about a guy he knew across the room, and talked too much about models he found attractive. I still wanted him to like me, though, still wanted him to kiss me.
And we did kiss eventually, back at his family’s apartment, later that evening when we went to listen to records. His parents were out of town, and he had the place to himself. I didn’t know anyone in Houston whose parents would leave them on their own at home overnight, and this impressed me. We hung out kissing for a few hours and then it was late. He walked me back to Mickey and Norman’s.
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