Like most writers, Gopnik is at his best when he has a fresh and specific subject at his disposal. His rambling thoughts on parenthood or exercise or "slowness" give him too much freedom to spin air-filled sentences on the obvious and overly generalized; in his essay about Times Square, "Times Regained," for example, he lazily calls anything that's not a chain store a "weird store." (Art gallery? Weird store.) His semi-reported pieces, however, particularly those focusing on Olivia's trials, result in genuine feeling and smart detail. She's the star of The Gopnik Show.

For the first half of the book, silent Olivia wisely observes life from the Gopniks' apartment window. When she finally speaks, it's in "Bumping Into Mr. Ravioli," perhaps the best piece in the book, not because it's cute--but because it's not cute. "Bumping Into Mr. Ravioli" introduces the 3-year-old's imaginary friend. She calls him, with what sounds like the toughness of a Brooklyn Mafia don, simply Ravioli. You can't help but imagine her all gesticulations and Marlon Brando frowns. "We had coffee, but then he had to run," she says of Ravioli. "He canceled lunch. Again."

Olivia's imaginary playmate is too busy to play with her. And he's a critic. "Ravioli read your book," she says to her father. "He didn't like it much." And then, as if nothing could seem more New York than that, Gopnik unveils the Second Fake Friend: "'Laurie, tell Ravioli I'm calling,' I heard Olivia say. I pressed her about who, exactly, Laurie was. Olivia shook her head. 'She works for Ravioli,' she said."

All of this lovely comedy leads to some of Gopnik's smartest analysis about the miseries of modern urban life and why his small daughter might have dreamed up a Type-A Italian heartbreaker and his secretary as her closest compatriots. "We exit the apartment into a still-dense nineteenth-century grid of street corners and restaurants full of people," he writes of New York's oppressive confluence of the Old World and the hypermodern, "and come home to the late-twentieth-century grid of faxes and e-mails and overwhelming incompleteness." Gopnik, rendered helpless by his child's cynicism, flashes some of his own soul. "We build rhetorical baffles around our lives to keep the crowding out, only to find that we have let nobody we love in."

Too often, though, the writer forgoes both humor and insight for a self-satisfaction he can't shake. In "First Thanksgiving: Densities," he and his wife and other parents at Luke's school conspire to make their kids fly in a production of Peter Pan. (Gopnik describes the school, which he calls "Artists & Anglers," this way: "Each class seems beautifully devised--a core of creative people's children, a sample of richer children, a frosting of minorities," giving the reader some idea of what paradise looks like to Condé Nast writers.) This entire charade--the parents' meetings, the physics of flying children--portends ludicrousness. Gopnik, instead, earnestly locates what's sweet about it. "The willingness of New York parents is bracing compared with the aloofness of French parents, or even of earlier generations of American parents. They will do anything to make their children fly," he writes, italics his, and he's serious.

Later, after much child-flight deliberation, a mischievous parent breaks the mold: "Why don't we just push them off a high place? They might fly." Readers of Through the Children's Gate will clap their hands at this shot of irreverence--Whee! Normal parental exasperation and human wickedness! Gopnik then dumps water on their heads: "The smile that went around the room was not a mordant one of knowledge," Gopnik writes, "but a happy one of promise: Our kids just might."

The kids, by the way, don't actually fly--or, in other words, feel any sort of rush of freedom. They only appear to fly for the benefit of their parents sitting in the audience. "But to us, the house in Peter Pan looks like an unobtainable idyll of domestic pleasure, a place to fly to," Gopnik writes in a typical paean to real estate.

Throughout the book, Gopnik weighs in on New York's over-gentrified, Victoria Secreted evolution, and on New Yorkers' collective nostalgia for the city's grunge years. New York is overrun with children, he writes, but that's not the real problem after all. Children like Olivia, ultimately, make better conversationalists than any you'll find in Williamsburg, anyway. When a man curses loudly, screaming the F-word, she says to her father, "Daddy, aren't you glad to be back in Yew Nork?" and you want to buy Olivia a beer.

The problem with present-day New York à la Gopnik is that it's overrun with smug New York parents. Members of this very special class feel as far from real life as Gopnik's map does from the actual streets of the city. Liberal, creative, "precariously" wealthy moms and dads bury themselves in the manageable problems of private school, the rewards of family-sized apartments and the terrifying task of protecting two small citizens against a metropolis of threats both justifiable and justifiably imaginary. Once upon a time these New Yorkers went through those gates to that Central Park playground, and were forever lost to the city.

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