Twenty-three-year-old George Lenhart is a struggling investment banker who comes from money so old that it’s completely disappeared. His default pose is one of ironic disdain, especially for Dartmouth classmate Harry Lombardi, a clumsy, social-climbing software entrepreneur who stands on the threshold of Internet millions. (The book is set in the ear-ly ’90s, when “the World Wide Web” was a new concept.) Both men are in love with Kate Goodenow, a WASP debutante who’s just blond and blank enough to absorb countless male fantasies –and the hostilities of most of her female peers–with a devil-may-care gaiety that hides her most calculating manipulations.

Though Macy’s written an essentially old-fashioned story about old-fashioned people, she is at her best surveying this society of misguided twentysomethings and the quirks of their Manhattan life: the Upper East Side skyscraper where Ivy League Wall Streeters take up residence; the way you introduce someone by identifying the schools he went to; the useless Saturday night when you skulk back to your apartment with junk food and a rental video, certain there’s a great party going on without you. When George tries to pick up an ironic Yalie named Delia with the line “You look familiar,” she responds: “We all do. Except we’ve all dropped a size and started waxing our eyebrows.”

Macy’s vision is a radical break from that of ’80s bad boys Bret Easton Ellis and Jay McInerney. Instead of overdosing, her characters just drink themselves giddy; they aspire to live like their grandparents; they’re astonishingly polite even as they turn treacherous. Describing the young-fogy culture, Macy writes, “We were the last generation of the century to come of age… We ought to have wanted to start a revolution; instead we bought cocktail shakers.” It’s a moment of deep nostalgia for the old barriers–right before they were mowed down by the Information Superhighway. Despite all his ambition, when Harry finally gets the girl at the top of the social ladder, he proves that the very ladder he struggled to climb has become completely irrelevant. For he embodies what most threatens the George Lenharts of the world: the fact that money has all but vanquished class in America today.

The Fundamentals of PlayCaitlin Macy (Random House) 289 pages. $24.95