Wendy and the Lost Boys (7 page)

A
nn-Ellen Lesser was a secretary, assistant to the headmistress, not long out of college, who began teaching philosophy as an extracurricular subject, her credential being that she had majored in philosophy in college. When the head of drama left, Miss Lesser was asked to take that over, too. It was a small school with limited resources; Wendy’s class had twenty-two girls in it.

The girls liked Miss Lesser. They thought she was hip, with appropriately “intellectual” looks—short pixie hair, dark-rimmed glasses. She encouraged them to experiment. It was the 1960s, after all. They did lots of theater of the absurd. “Existentialism was in,” she recalled. They took scenes from short stories, put them to music, and performed an antiwar piece.

“This was an all-girls’ school,” she said. “You either did the one or two bad plays that were all women characters or you do other stuff and bother some boys from McBurney to help out and watch them get destroyed by our teenage girls.”

As an adult, speaking at the dedication of a new performing-arts center at Calhoun in 2004, Wendy talked about Miss Lesser’s productions:

One year, she had an idea to put on a play in our auditorium, which was at that time the Jewish Community Center on West Eighty-ninth Street. The play she chose was Günter Grass’s
The Wicked Cooks.
Günter Grass, for those of you who don’t know, had two major claims to fame. The first was that he won the Nobel Prize for Literature in 1999. The second was that he had an all-girl high-school production of the absurdist play
The Wicked Cooks.

My parents were in Europe during our rehearsal period, and my big sister Sandy, who was an executive at General Foods, came to stay with me. At night I would rehearse my lines with her, and she would make her Maxwell House account-executive buddies listen to it and ask them if it made any sense to them. There would be a stunned look on their faces, and they would ask me, “Why isn’t your school doing
Annie
?”

The day of the performance arrived, and the proud parent body sat in the theater as we came out onstage with giant chefs’ hats and aprons and began reciting lines in unison, like, “The moon is a potato / The star is a tomato / And everywhere are cooks / In all the halls and nooks.” I distinctly remember seeing jaws dropping and a hushed silence, and at the end a burst of parental applause for the completely incomprehensible event.

Miss Lesser was amused by Wendy’s account, which became part of the school’s lore, eventually appearing on the Calhoun Web site, but Miss Lesser had a correction. After pointing out that the
Wicked Cooks
production was the handiwork of the previous drama adviser, she observed that Sandy’s Maxwell House colleagues couldn’t have asked why the students didn’t do
Annie
instead of
Wicked Cooks.

Annie
didn’t premiere until 1977, a decade after Wendy graduated from Calhoun.

“It’s still a great story, but there is a bit of poetic license,” said Miss Lesser.

W
endy had the most interesting mind of any student I ever had, ” said Ann-Ellen Lesser. “There’s smart, which is what comes up on the IQ test. And then there’s intelligence that has the element of imagination in it. Wendy had real intelligence, imagination, the ability to see beyond what was in front of her.”

Yet during her years at Calhoun, no one was predicting a Pulitzer Prize for Wendy Wasserstein. Of more immediate concern: would her grades improve enough to get her into a good college?

School records report tardiness twelve times in a single semester one year. Her math grades hovered between C-plus and B-minus, and she consistently received C’s in French and D’s in gym.

The curriculum was rigorous and the teachers demanding. They were quick to point out weaknesses—a slapdash quality to her work—even in subjects where she excelled, like history and English. “Wendy’s knowledge of history is extensive,” wrote a teacher in her midterm report junior year. “The mechanics of her writing are poor—a fact which belies the intelligence of her thinking.”

To escalate her prospects for college, she was encouraged to take summer courses at elite boarding schools. The programs were known to be exacting, and, Wendy understood, it wouldn’t hurt to have names like Exeter and Andover on her application. She’d been learning the importance of name brands and always made sure to note that she took lessons at June Taylor’s School of Dance, not just any studio. (Taylor’s choreography featured Rockettes’-style high kicks; her dancers were regular performers on
The Jackie Gleason Show,
a popular TV variety program in the 1950s and ’60s.)

After sophomore year she attended the summer program at the Phillips Academy, Andover, in Massachusetts, where she succumbed to the lure of the New England countryside and the school’s exalted aura. That encounter began a lifelong infatuation with charming academic campuses situated in rarefied settings.

She returned from Andover to Calhoun a better student but not good enough for the headmistresses, Cosmey and Parmelee. Midway through her junior year, they offered this guarded evaluation: “Wendy has produced a good report. We are especially glad to note that she is passing physical education. Comments should be studied carefully, for Wendy needs now to take giant steps in academic growth, to begin to prepare for greater challenges next year and in college.”

The following summer she returned to New England for another summer program, this time at the Phillips Exeter Academy in New Hampshire, where she was challenged by unsparing faculty. She took serious subjects—economics, philosophy, music appreciation—and wrote dull, lengthy papers in longhand. “Wendy, you have written over four thousand words when the assignment called for fifteen hundred,” wrote a testy professor. “You have too much bulk here—repetitious passages, excessively long quotations, redundancies, and superfluous sections. A good rewriting of the entire essay could reduce it by half without losing any essential material. I appreciate your industry and sincerity in this enterprise, but I urge you to be more efficient by being precise and concise.”

Regular grade—B-minus.

Grade due to penalty for lateness—C-plus.

Despite the grueling assessments and the repeated grade reductions for sloppiness and turning her papers in late, she produced remarkable work for a fifteen-year-old. Her papers demonstrate great effort and a complex intellect; she struggled to grasp conventional wisdom and then put her own stamp on it. In a paper analyzing the work of George Bernard Shaw, she wrote a snappy opening line that could be seen as a guidepost for a future writer of provocative plays: “The saint does not bring peace on earth and good will among men. The saint, rather, makes the world uncomfortable to live in.”

W
hen Wendy applied to college, she had begun to think that the University of Michigan, which both Sandy and Bruce attended, wasn’t for her. She didn’t want to follow Georgette’s path either. Her middle sister had traveled in Europe after graduating from Hood College, then a small girls’ school in Maryland, and was back in New York, taking classes at the New School. In the fall of Wendy’s senior year, Georgette followed Marjorie Morningstar’s example. Marjorie had succumbed to a Jewish lawyer; Georgette married a Jewish doctor. Albert Levis didn’t exactly conform to the cliché; he was born in Greece, was studying clinical psychiatry at Yale, and exhibited an eccentric intelligence. Wendy didn’t find him dull, just weird.

Georgette appeared rail thin and ethereal in her bridal gown. The wedding was a lavish affair at the Plaza Hotel, where Lola scandalized her more religious Schleifer relatives by serving shrimp. Wendy was reminded, looking at “Gorgeous,” of her own failings in the get-slim department. She was also concerned, wondering if Georgette hadn’t been cornered into making a wrong decision. Wendy discovered that the corollary to feeling superior and inferior was the unpleasant sensation of betraying a sister, whom she loved, by both mocking her choice yet in some ways envying her.

Her own ambitions had begun to take amorphous shape during her sojourn in the Manhattan private-school system. She turned her sights toward the Seven Sisters colleges, female counterparts of the Ivy League schools, which were then primarily all male, except for Cornell.

She applied to Michigan, but her heart was set on Mount Holyoke College, a world apart from Wendy’s cloistered Jewish world in New York.

While her grades were a mixed bag, her recommendations were stellar. “Best student in five years,” wrote her history teacher. “Quality of mind is exceptional. Thinking is imaginative and original. Is an intellectual rebel but does not as yet have the self-confidence to fight or argue for her conclusions.”

The headmistresses chimed in: “An excellent, critical independent logical thinker,” they wrote; “weaknesses stem from carelessness. Is gradually learning not to brush aside details. A born leader. Recommend enthusiastically.”

Before completing the application process, in the fall of 1966 Wendy won an essay-writing contest sponsored by the World Youth Forum, a program created after World War II by the
New York Herald Tribune.
The idea was to promote international understanding by introducing young people from around the world to one another. Wendy saw an additional benefit in the program: “my secret weapon for gaining admittance to the college of my choice.” The
Herald Tribune
folded in 1966, but WCBS-TV took over sponsorship of the program. The winners were scheduled to take a trip to Europe the following summer.

Wendy and other Youth Forum winners appeared on a local Saturday-afternoon television program called
The World We Want,
where students were asked questions like “How would you solve New York City’s problems?”

When the program was broadcast, her mother provided a ratings boost. Lola went to the television department at Bloomingdale’s and turned all the channels to
The World We Want.
That heady moment was quickly deflated: in April Wendy received a polite letter from the Mount Holyoke admissions office informing her that she was wait-listed.

The wait list was another stinging reminder that she might not be good enough. Calhoun hadn’t been her first choice of the Manhattan private schools. She didn’t get into Dalton, then a girls’ school, favored by prosperous secular Jews. She was too intimidated to apply to the highly regarded Brearley School, which she imagined as a Wasp enclave, filled with thin, blond, beautiful girls, floating effortlessly through life.

Once again her merit was called into question.

Wendy would be such a good student, if only her work were neater, less convoluted, better.

Wendy would be such a pretty girl, if only she would lose weight.

Wendy would be perfect, if only she were someone else.

T
he blow from being wait-listed at Mount Holyoke was offset—somewhat—by romance.

James Kaplan lived a few blocks from Wendy, in the Imperial House, a slightly fancier version of the Wassersteins’ white brick apartment building. Wendy’s Calhoun classmate Kathy Roskind lived in Imperial House, too. The two girls became diet buddies, being the not-slender daughters of mothers who were annoyingly skinny. Mrs. Roskind, who was five feet, two inches and weighed ninety pounds, frequently reminded the girls of the upwardly mobile Jewish mother’s motto: “You can never be too rich or too thin.”

Mrs. Roskind was a chain smoker with emphysema, who often stayed home. She enjoyed Wendy, who used to amuse her friend’s mother by singing the hit title song from the movie
Georgy Girl.
The lyrics—about a girl who appeared to be carefree but felt lonely inside—hit home.

Wendy wasn’t the only teenage girl to be infatuated with
Georgy Girl,
about a large, awkward young woman who yearns for love and ends up taking care of her beautiful roommate’s baby. The 1966 movie, though presented as a convoluted Cinderella story, tapped into feelings about deep issues: the nature of marriage, the lure of motherhood, the urge to be free, the desire to be loved for what you were.

Lynn Redgrave would become known in subsequent years as the spokesperson for the Weight Watchers diet plan. In 1966 she became, for girls like Wendy and Kathy, a rebuttal to Twiggy, the anorexic, doe-eyed teenage supermodel who made starvation a fashion statement. With Twiggy as the ideal, the pressure to lose weight was frequently disproportionate to the weight there was to lose. Photographs of Wendy and Kathy in the
Inkspot,
the Calhoun yearbook, show attractive girls who are not slim but certainly not fat. (Wendy’s weight fluctuated, but in high school she often weighed around 130 pounds, on a five-foot-six-inch frame.) Wendy appears open yet guarded; she has a way of looking at the camera while seeming to look away.

Their mothers sent the girls to the same Fifth Avenue diet doctor, whose seven-dollars-a-visit charge included amphetamines for weight control. The rainbow-colored pills made Wendy nervous, so she threw hers away. She and Kathy went directly from the doctor’s office to the drugstore, where they would buy (and consume) three candy bars each and vow to start their diets the next day.

Wendy pretended to be insouciant, but there was no way to feel good about Lola’s constant pressure to lose weight. When they walked down the street together, Lola—wearing a dance leotard underneath her fur coat—would wave at the crowds passing by and say to Wendy, “They are all looking at you and thinking, ‘Look at that fat girl.’ ”

Wendy noticed James Kaplan and asked Kathy to introduce her to him. Kathy was apprehensive. She was very aware of Jimmy Kaplan but was certain he was not at all aware of her existence. He was nice-looking, smart, Jewish, and extremely well credentialed: he went to Horace Mann, one of the city’s most exclusive prep schools for boys. The fetching ribbon around this attractive package: Jimmy Kaplan had already been accepted to Yale.