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On those nights of cultural cat burglary, I was given the gift of extraordinary artistic riches. But in retrospect I see a strangely forlorn side to it all. On my furtive McCarter capers I was a solitary teen, alone in a crowd of privileged adult sophisticates, creeping around like a spy behind enemy lines. Once again I was straddling two worlds, and in one of them I was a secretive loner.

In the other world, I continued to fly high. All through my senior year I seemed to leap from one shining moment to another. In my schoolwork I got nothing but A’s. As Student Council president I presided over weekly all-school assemblies, crafting a droll, self-deprecating public persona. I initiated a series of after-school concerts featuring solo performances by student musicians. In the foyer of the school library I created a gallery for student art, and its initial offering was an exhibition of my own watercolors. I invited actors from the McCarter Company to speak before meetings of the Tower Thespians, giving myself the unique opportunity of introducing a spirited Shakespearean monologue, performed by my own father. I even created a cottage industry of woodcut Christmas cards and peddled them to the parents of my classmates. My eagerness to please verged on the pathological. At the awards assembly at the end of the year, I routed my competition. Oh, what a good boy was I!

But in the gleaming patina of such a triumphalist year, cracks occasionally appeared. In my year-long victory lap, I experienced a couple of queasy moments. And it’s a good thing that I did: they taught me more than I could ever have learned in schoolbooks.

The first of these moments shows what a rarefied and repressed social circle I was traveling in at Princeton High. One of my classes that year was Advanced Placement Social Studies. Our teacher was a squat, round, wryly cynical man named Mr. Roufberg. One day, Mr. Roufberg surprised us with an unusual assignment. He asked us a simple question: “What is the issue in your life that most concerns you?” He gave us all ten minutes to write down anonymous answers and pass them in. A day later, he reported on the results of his pop survey, rattling off our deep concerns with deadpan bemusement. The answers were heavily weighted toward such ponderous topics as nuclear disarmament, world poverty, and civil rights. I myself had written down some garbage about creeping commercialism.

Then Mr. Roufberg sprung a surprise, hitting us with a kind of sociopolitical ambush. He proceeded to summarize the answers to the same question that had been written by students from his other classes, a few levels lower in the school’s rigid social hierarchy. These answers were stunningly different from ours, far more personal and far more urgent.

Should I go steady?

Should I pet?

Should I have sex?

Should I tell my parents that I’ve had sex?

What’ll I do if I’m pregnant?

Listening to this list, all of us in AP Social Studies felt curiously chastened. We flushed and lowered our eyes. Our skin prickled with embarrassment. We were accustomed to feeling an offhand superiority to the working-class majority of our classmates — smarter, more worldly and sophisticated. Yet here they were, these earnest, impassioned townies, anonymously expressing emotions that we barely allowed ourselves. Creeping commercialism? Who the hell cared? Could it be that we were learning a lot more about social studies and they were learning a lot more about life?

And then there was my hard-earned lesson in political chicanery. My sweet-natured mother turned downright wrathful one day when I bragged about one of my Student Council initiatives. As president, I had proposed to my Executive Committee that we use Student Council funds to purchase several of my Christmas cards to send to members of the high school faculty. The committee had briskly passed the measure and I had handily pocketed thirty-five bucks on the deal. When I came home brandishing a check and crowing about my entrepreneurial coup, Mom’s face turned crimson. In no uncertain terms, she ordered me to return the money and make the cards my personal gift to the school. Then she sat me down and explained to me, in words that seared into my brain, the concept of “conflict of interest.” What I had done, she said, was enough to get me impeached from any elected office out there in the real world. I was seventeen years old by this time. At such an age, I certainly should have known better. What kind of amoral idiot needed such elementary ethical counseling? I learned about conflict of interest that day, but I also learned how blithely corruptible I was. Corruptible and, I might add, unregenerate: I recall, to my shame, that I never quite got around to returning that check.

Finally there was Patty Brown. Her story was my first real insight into the ugly realities of racism. In those days, the American Friends Service Committee ran a program that brought talented African-American high school students north from segregated schools in the Deep South. The idea was to give them a year-long experience of the fully integrated and presumably more enlightened world of public education in the North. This was 1962, remember, and the civil rights movement was only just beginning to take hold. As such, the program was well ahead of its time. If it was a little patronizing and naïve, it was also bold, idealistic, and worthy.

The program sent two students, a girl and a boy, to join the Junior Class of Princeton High School in my senior year. The girl’s name was Patty Brown. Patty was short, compact, and bespectacled, a smart, vibrant kid with a dazzling smile, a daring sense of humor, and an explosive laugh. It was easy to see what had made her a star student in her Alabama school and a prime candidate for the AFS program. She arrived in Princeton ready to seize this new experience with both hands, and her classmates responded in kind. She and I hit it off instantly and maintained a fun, teasing relationship that entire year.

When spring came around, Patty asked me to take her to her Junior Class prom. She asked over the telephone. Her voice was halting and uncharacteristically shy. Clearly the request had taken all her courage. Near tears, she touchingly added that she would understand if I felt I had to say no. I said yes. And so, for what was surely the first time in the history of PHS, a white male Student Council president would escort a black girl to a school prom. And not only that. The vice president, an African-American junior named Art Brooks, invited a white girl and asked Patty and me to double date. I said yes to this, too. Long before its time, we were all set to enact a four-character version of Hairspray.

As our plans fell into place, my mother nearly burst with pride. She saw the event as a radical social statement on my part, and it warmed the cockles of her lefty heart. When the evening arrived, I did my best to ignore the political baggage she had attached to it. The four of us gathered at the home of Art’s date and we ate supper together. The air was charged with nervous anxiety, but probably no more so than any of our classmates were feeling, in households all over town. We ate together in near-silence. The anarchic humor that Patty and I usually shared had disappeared. We were a perfectly typical quartet of shy, tentative teenagers heading to the prom.