Her first novel, Prep, which took her three years to write, concerns a girl, Lee Fiora, from South Bend, Indiana, who goes to Ault School, an elite boarding school near Boston, Massachusetts. Some think Ault is a thinly veiled Groton School, but others say it is based on the two years Sittenfeld spent teaching at St. Albans School in DC. The plot deals with coming of age, self-identity, and class distinctions in the preppy and competitive atmosphere.
Reviews of Prep were mixed, with views ranging from highly laudatory to those who said that it was a well-written but weakly plotted story that was buoyed by strong detail and narration. Some saluted the book for its verisimilitude, including Elissa Schappell, who wrote in the New York Times Review of Books: "Sittenfeld's dialogue is so convincing that one wonders if she didn't wear a wire under her hockey kilt." The New York Times named Prep one of their top five works of fiction for 2005.
Less positively, a review in Publishers Weekly stated, "The book meanders on its way, light on plot, but saturated with heartbreaking humor and written in clean prose. Sittenfeld . . . proves herself a natural in this poignant, truthful book." Critics have also questioned how much of the story is pure memoir instead of fiction.
The book has been optioned by Paramount Pictures, which also has an unrelated project with the same name, under its MTV Films umbrella.
The Man of My Dreams
Sittenfeld's second novel, called The Man of My Dreams, was published in May 2006 by Random House. It follows a girl named Hannah from the end of her 8th grade year through her college years at Tufts and into her late twenties. Both in comparison to Prep and other novels, The Man of My Dreams has gathered mixed reviews with much of the same praise and criticism Prep has garnered.
Sittenfeld's third novel, called American Wife (2008), is the tale of Alice Blackwell, a fictional character who shares many similarities with former First Lady Laura Bush. In the novel, Blackwell is an only child who grows up in a Democratic family. As a high school student, Blackwell kills a friend in an auto accident. She also has an illegal abortion and discovers that her grandmother is a secret lesbian. She meets, falls in love with, and marries the wild son of an elite Republican family. Her husband rises in politics to the office of president, and, although Blackwell staunchly disagrees with her husband's politics, she continues to love him.
In November 2011, it was announced that Red Crown Productions had begun work on a film version, with the adaptation be written by Academy Award-nominated screenwriter Ron Nyswaner.
Sisterland was published on June 25, 2013. The book's protagonist Kate is an identical twin.