Tad Friend’s life reads like lost John Cheever: With WASP stock on both sides of the family, he grew up in a maze of rigid expectations, where “brisk and amiable” were the watchwords, and unexpected outbursts were never spoken of again. Cheerful Money: Me, My Family, And The Last Days Of WASP Splendor functions as not only a chronicle of Friend’s determination to put the anxieties of his upbringing behind him, but also as WASP taxonomy—a bird-watching guide for people.
The quirks of Friend’s upbringing in upstate New York and Main Line Pennsylvania weren’t evident until he discovered most families don’t “name their dogs after liquor and their cars after dogs and their children after their ancestors.” By Friend’s generation, the family money had nearly run out, but enough remained to expose him and his siblings Pier and Timmie to the hand of advantage, such that they struggled to escape its grasp while still loath to give up summering in the Hamptons and singing Revolutionary War songs around the Christmas tree. Once surrounded by relatives whose invisible censure was a constant presence—his grandfather’s second wife banished him from visiting after catching him licking a spoon after a bowl of ice cream—Friend continued to ripen in self-consciousness as a prep-school student, and later at Harvard (a departure itself, in a family of Yalies) as he attempted to puzzle out to what manor, exactly, he’d been born.
Now a staff writer at The New Yorker, Friend reconstructs a string of family secrets—including the circumstances under which his maternal grandfather left his family, buried under a nest of falsehoods by his cheerfully distant mother. These, he uses as a prism for viewing his duty of ministering to his own lonely dad and contemplating his children’s birth. But he builds on the opportunity to play archaeologist to a disappearing stratum of culture, not just a familial decline. It wouldn’t be possible without his sometimes alarming candor about former lovers, personal shortcomings, and that most WASPish taboo, dollar signs. (What the lyrical descriptions of summers on Georgica Pond whisper, the revelations of Friend’s therapy bills shout.)
Friend holds himself responsible for not carrying on the traditions of his forebears, but Cheerful Money offers a deadpan defense of the WASP culture whose outline it simultaneously traces. The man who once used a phrase from Abraham Lincoln’s troop reports to buck himself up after bad dates pays homage to that stiff upper lip as more pervasive, complex, and ultimately beneficial than a mere question of upbringing.