Love’s labors

IF Curtis Sittenfeld’s bestselling debut novel, “Prep,” had been merely a dishy look at an elite boarding school, its success would be easy to dismiss as part of a larger social phenomenon: our unquenchable curiosity about the privileged. “Prep,” however, was more than a J. Crew catalog or a parable about class or even a coming-of-age story. Rather, it captured an experience many readers know all too well, the feeling of floating on the fringes of a party, where everyone is prettier, smarter, wealthier and more worthy than you are.

Prep school and dating, it turns out, have a lot in common. Both are perilous worlds governed by strict codes of conduct. In “Prep,” Lee Fiora, the outsider protagonist, recognizes the symbols -- the pattern of a bedspread, the satin lining of a peacoat -- in a tone that blends mockery with genuine wonder. Sittenfeld’s second novel, “The Man of My Dreams,” aspires to a similar acuity, following a young woman, Hannah Gavener, as she navigates the thickets of romance.

Hannah, though, is no Lee Fiora; by comparison, she is relatively inert. She has big thighs, low self-esteem, a judgmental eye and a determined romantic streak. She sees the world as dizzying, but ultimately decipherable and just. “She is on a balance beam, and if she says anything too corny or too clinical, she’ll tip to one side,” Sittenfeld writes partway through the book. “But possibly, if she says the exact right thing, Henry will fall in love with her.” Unfortunately for Hannah, she almost always finds herself saying precisely the wrong thing. Still, her belief that finding love is a matter of discovering and following the right script is genuine, even as she grows older and experiences disappointment after disappointment.

“The Man of My Dreams” follows Hannah through 14 years’ worth of fixations and relationships, beginning with her crush on Kiefer Sutherland at age 14. One chapter is devoted to Mike -- boring, predictable Mike, who says “making love” and listens to jazz. He is, Hannah tells us, “the man who is with you completely.” Another chapter gives us Oliver, “the man who is with you but not with you.” Oliver has a sharp wit, a Kiwi accent, good looks and a love of sex -- whenever and wherever and with whomever he can. Mostly, there is Henry, the only man who comes close to playing the novel’s title role. Henry is kind, intelligent, thoughtful and handsome. He teaches Hannah the state motto of Missouri, how to parallel park and how to laugh at herself. But he never kisses her. Henry is “the man who will get as close to you as he can without ever becoming yours.”

Other men float in and out of the novel, but these three -- along with Hannah’s dad, who abandoned his family when Hannah was 14 -- are the only ones who matter. For her, they are “models -- templates, almost.” As she explains, “It would be arrogant to claim no other dynamics exist just because I haven’t experienced them, but I have to say that I can’t imagine what they are. I hope that I am wrong.”

Hannah is wrong, of course -- but oddly, this is where “The Man of My Dreams” falters. There is no dynamic here that can’t be decoded, which means she is defined almost entirely in terms of her relationships. This is due in part to her own myopia, but also to the structure of the narrative: Hannah doesn’t have hobbies, interests or real friends -- nothing outside her interactions with men. The only other thing that motivates her is paying off her student loans, and even that’s to stick it to dear old dad. When, at the book’s end, she ostensibly finds fulfillment teaching autistic children, it feels forced. Her emotional world is too constrained. Such a limited worldview makes for a limited character; to show how much she’s grown, she tells a story about one of her students, but she seems equally pleased that she’s no longer embarrassed to talk to people “with food in [her] teeth.” Even in a world where small victories matter, it is difficult to call this a real triumph.

Tellingly, the most appealing character in the novel is the one for whom relationships are most fluid. Fig, Hannah’s sexpot cousin, begins merely as an undermining figure. (“It’s so cute that you still live in a dorm even though you’re a senior,” she tells Hannah.) She is beautiful and reckless and manipulative, with what Oliver calls “magnificent breasts” -- in short, everything Hannah is not. It’s no surprise, however, when she turns out to be more complex. Henry describes her as “a wild card” -- and it’s true: Fig has an ineffable, unpredictable energy. She lives off-script. When Fig is in the scene, Sittenfeld’s writing sparks.

Sittenfeld gets a lot about the fraught world of dating just right: the anxiety, the careful rituals, the unflagging optimism that jockeys constantly with a sense of impending doom. She shows how complicated dating can be in the postfeminist age, where the expectations are not always clear. Her skewering of men is often funny and sharp. But if her portrayals are wholly recognizable, their range is narrow and flat. In the end, Hannah is still looking for the right template rather than the right person. Stereotypes and accouterments are also important in “Prep,” but Lee has a flinty integrity and independence that Hannah lacks. It is Lee’s voice, not the monogrammed towels, that animates “Prep.” In her new novel, Sittenfeld’s voice seems attenuated, a single tune instead of an opera. Hannah’s low self-esteem is sad, but it’s hard to picture her any other way. *