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Psst, Serena is a slut. Pass it on.

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Cecily von Ziegesar in Central Park, surrounded by some of her teenage fans.  

Gossip Girl operates on just that borderline between irresistible trash and the smarter stuff, so perhaps it makes sense that it arose out of a marketing brainstorm. At the time, Von Ziegesar—who had dropped out of the creative-writing program at the University of Arizona—was working as an assistant editor at 17th Street Productions (later called Alloy Entertainment), a synergistic packaging concern aimed at “concepting” properties for teenage girls. Her colleagues included Ann Brashares, now the author of Alloy’s popular Sisterhood of the Traveling Pants series. And the company had a long history with teen lit: It originated as a distributor for Sweet Valley High, the brainchild of Francine Pascal—who never wrote a single Sweet Valley book, but plotted them all in out-loud brainstorms.

Sweet Valley ruled the teen literary roost throughout the eighties, delighting a generation with the adventures of identical twins Elizabeth (good) and Jessica (evil). The Sweet Valley stories were packed with exciting events—overdoses! kidnappings!—yet despite their excesses, they were resolutely moral, with bad girl Jessica endlessly punished for her naughty ways. Sales nosedived in the mid-nineties, when a new culture rose up with a thousand alternatives to reading—from video games to MTV, the Internet, reality television, and that hydra of adolescent programming, the WB.

In response to this dim market, the company repositioned itself to meet the new business model head on. During a meeting, someone suggested they exploit the newly powerful Internet by launching an anonymous “Web mistress”—call her Gossip Girl. Leslie Morgenstein, the president of Alloy Entertainment, sheepishly acknowledges that the original idea was not for a book per se but a viral marketing hoax: Alloy would concoct a Website, seemingly written by a teen Hedda Hopper, and once the site got “buzz,” launch projects by that invented author. The plan was quickly abandoned. “It was too complicated, and too easy to get caught,” Morgenstein says. Instead, the company presented its book proposal in e-mail, at a time when few publishers checked their in-boxes. It got only one bite, but it was a hard one: Cindy Eagan, now executive editor at Little, Brown. “It was the first e-mail submission I’d ever heard of,” she says. “And I was intrigued by the name. Who doesn’t love gossip?”

At a meeting with 17th Street, Eagan asked who had written the proposal. Von Ziegesar raised her hand. “Cecily took the assignment and knocked it out of the park,” says Morgenstein.

At the time, the project had no plot or specific milieu. Von Ziegesar decided to set it in the world she knew best, the Constance Billard School (a ringer for Nightingale-Bamford), and she created an ensemble of distinctive New York types: the effortlessly lucky blonde, Serena; her envious brunette “frenemy,” Blair; and a cohort of preppy stoner boys, sardonic Williamsburg artists, and rumor-spreading wannabes—a Greek chorus of the cafeteria table. The books themselves would be narrated by Gossip Girl herself (or himself), an anonymous blogger with a gimlet-eyed take on the world around her. Or him.

Von Ziegesar began by modeling Gossip Girl on Edith Wharton’s The Age of Innocence, that earlier tale of a closed New York society. Serena van der Woodsen, a beauty kicked out of boarding school, returns to her old school, only to be dogged by envious rumors of lesbianism and love children. Von Ziegesar’s first draft was horribly high-minded, a fusty Wharton imitation; she quickly trashed it and adopted the brassy tones of Gossip Girl, who ends her dispatches with the teasing sign-off, “You know you love me.”

From the beginning, Von Ziegesar added her own raw and distinctive touches, not all of which went over with Little, Brown. In Gossip Girl No. 1, Serena falls serendipitously into modeling and—like Carrie Bradshaw—ends up pictured in bus ads all over Manhattan. However, unlike Carrie, the shots (at least in Von Ziegesar’s initial draft) were artistic close-ups of her anus—part of a series of shocking celebrity portraits. Little, Brown suggested Von Ziegesar substitute a belly button. She chose a compromise that works hilariously well—the orifice is itself a mystery, even to Blair, who is tortured by her former friend’s sudden fame. “Was it her belly button? It looked like the dark pit at the center of a peach . . . Blair could never get completely away—Serena was fucking everywhere.”

The author did no research among teens. “I don’t know what that says about me—that I didn’t mature?” she says. “Or, no, that’s not fair to the reader. It just says teenagers aren’t that different from adults.” Still, the books managed to be astonishingly prescient, picking up trends before the curve. In one plot, a freshman girl is filmed, thong exposed, during a Central Park makeout, only to have the footage ricochet across the Internet—a year before Paris Hilton’s sex tape. Von Ziegesar dramatized mean girls before Mean Girls, and picked up early on blogging, instant-messaging, micro-celebrity, and the kudzu-like growth of Hollywood gossip itself.

And despite Von Ziegesar’s stated intentions, her books do seem to teach their readers a lesson of sorts. For all its cynicism, Gossip Girl might be seen as a blueprint for reputation management on a massive scale—whether sudden fame or sudden notoriety. Serena is an effortlessly lucky flake, but she’s also an exceedingly benign individual, a role model for rising above jealousy: Never respond, smile pretty, feel no shame, expect attention as your due, and move on to the next bit of good luck.

Meanwhile, despite having scandalized her old school—where her headmistress was not thrilled to have her students portrayed as party girls—Von Ziegesar has made amends. “They have a different headmistress now, who was a little wary of me,” she says. Then Von Ziegesar wrote an essay for the Nightingale-Bamford school paper, describing her “warm and fuzzy” feelings for her alma mater. “She wrote me a nice letter saying, ‘I always thought you were like the girls in your books, but now I realize I was wrong.’ And she said, ‘Thank God.’ ” Von Ziegesar laughs—then looks thoughtful. “Still, it’s funny. They’ve never invited me once to their book fair.”


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