My husband's grandparents used to pay him a dollar an hour to nap. Tad Friend's parents tried to entice their three children into "sunnier moods" with what they called "Cheerful Money," a 25-cent reward dropped into a glass jar whenever "one of us demonstrated good humor under duress or was spontaneously helpful."

Using cash as a "behavioral-management tool" is just one Wasp peccadillo that Friend nails in Cheerful Money, a suave, sharp-witted, generally intoxicating but occasionally sobering expose of his native culture. He notes that the acronym for White Anglo-Saxon Protestant, popularized in 1964 by sociologist E. Digby Baltzell, is both redundant and inexact, and he proceeds to delineate a more precise picture in his fond but probing personal history.

In a culture that values decorum and reticence, revealing private family matters requires gumption or, in Wasp-speak, "sand." Friend discovered that after his 2006 New Yorker profile of his late mother "rattled my family in ways that slowed the writing of this book yet clarified its true subject."

Born in 1962, Friend grew up in Buffalo, N.Y., and Swarthmore, Pa., where his father was president of Swarthmore College. His forebears came to America in the mid-17th century but didn't become "smashingly rich" — from steel, coal and banking — until the beginning of the 20th century. His great-great grandfather employed 18 servants. While most of the men in his family attended St. Paul's School and Yale, Friend diverged as far as Shipley and Harvard.

Since the Great Depression, conservation and preservation have become the mainstays of the family, trying "to caulk the seams" of their leaky financial vessel. Family estates, which once included a Pittsburgh mansion and a Vermont farm, are now reduced to a summer home on exclusive Georgica Pond on Long Island, which they rent to cover expenses.

Friend is not the first to write about emotionally constipated ancestors, the waning of Wasp power or the painful erosion of beloved family holdings: George Howe Colt's The Big House springs to mind. But, drawn to "the ruinous romance of loss," Friend is one of the least whiny and most incisive insiders to chronicle this privileged world, and he does so with style and soul.

This is thanks, in part, to reportorial skills sharpened by years of work at The New Yorker, for whom he files dispatches about another quirky subculture — Hollywood — for his "Letters from California" (despite living in Brooklyn Heights with his wife, New York Times food writer Amanda Hesser, and their twins).

Perhaps equally critical is the insight gained from having spent "my inheritance and then some" on 13 years of psychoanalysis to assuage a "feeling of disconnection" that began in early childhood.

He's still unlikely to fill his Cheerful Money jar anytime soon, but we're the richer for such salty observations as why Wasps like rough-housing with dogs (it allows them to be affectionate and get dirty), how they pronounce buffet ("boo-fay," not "buff-ay") and use euphemisms to disguise their heavy drinking (they never have another; instead, they refresh or repair the drink already in hand). Bottoms up.

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