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Wasserstein compares the gathering momentum of her theatrical career to the children's story The Little Engine That Could. Heidi was written in 1987 after a frustrating period that included a musical that never made it out of workshop readings and a filmscript for Steven Spielberg that was shelved. Then, as now, she was living in a Greenwich Village apartment, with no formal attachments aside from a cat named Ginger. Relentlessly social, Wasserstein has built a life revolving around an intricate network of friendships, many with other playwrights. But writing Heidi represented, in part, an acknowledgment that Wasserstein, like her heroine, is a woman alone. As Andre Bishop, the artistic director of Playwrights Horizon, puts it, "Wendy is now coming into her own as a writer and a person, and those two are very much linked."
Even so, Wasserstein's natural medium remains humor. As she explained in a painfully honest essay called "Funny Girl" in New York Woman magazine, "I don't think about being funny very much because it's how I get by. For me it's always been a way to be likable but removed." The result is that outsiders can misinterpret her manner and mistakenly belittle her talent. Playwright Terrence McNally complains that "what people often miss about Wendy is the thoughtful, passionate, mature womanly side of her. She is far more interesting as a mature artist than as this giggling, girlish, daughter-person that people want to take care of."
A few days after Heidi opened on Broadway, Wendy's parents Lola and Morris Wasserstein were asked about their youngest daughter, the successful playwright. Much of the conversation sounded like a leftover scene from Isn't It Romantic. "We're very proud," said Lola, who even in her 70s takes four dance classes a day. "But there's a vacuum," added Morris, a prosperous Manhattan businessman. "Where's the children? Where's the husband?" Here Lola broke in, "Normally, I'm the one to say that. But today I'm on good behavior." A few moments later, the Wassersteins were asked how many grandchildren they have. "Nine," said Lola, "and we're waiting for the tenth." To underline the point, Morris chimed in, "We're waiting for Wendy. Patiently."
Both of these doting parents are Jewish emigres from central Europe who came to New York City as children in the late 1920s. For years, Lola has been the richest source of her daughter's comic material. "Do you know what my mother said to me on the opening night of Uncommon Women?" Wasserstein asks rhetorically. " 'Wendy, where did you get those shoes?' " When Isn't It Romantic was playing off-Broadway, Wasserstein's parents would stroll over to the theater and canvass the crowd. "My mother would call and say, 'Oh, what well-dressed people,' " Wasserstein recalls. "She was proud of me because someone with a long skirt went to see my play."