Cheerful Money was always going to be a book I’d read the moment it hit the shelves, and I found it very enjoyable. It is in some ways easier to take than George Colt’s The Big House which traffics heavily in nostalgia. For Tad Friend, his WASP heritage resides more in people and habits than in one house — this is more truly a memoir, with incisive portraits of numerous ancestors and their emotional patterns. Friend is entertaining and perceptive. For instance, very early on he locates the tribe: “They lived in a floating Ruritania loosely bounded by L.L. Bean to the north, the shingle style to the east, Robert Falcon Scott’s doomed polar expedition to the south, and the limits of Horace Greeley’s optimism to the west.” He takes on, along the way, the standard cultural markers like food and drink, clubs, nicknames (Tad, for instance), and money. “Old money, having received its money, treats it with custodial anxiety; new money, having earned it, believes it should be used.” Yep.
But this is not a rehash of The Official Preppy Handbook (which, I proudly note, he quotes in a couple of places), because Friend is after deeper illumination, and the narrative mirroring the story of his family is the tale of how he shed his carapace. Some of this is dull (the section excerpted in The Paris Review, for instance, seemed like a tame replay of Jay McInerney) and some of it made me squirm. Details about his analysis? Isn’t a little bit unseemly? I was also floored by the calm, earnest, post-therapeutic tone of his heart-felt adult conversations with both of his parents. So I guess that shrink has done a terrific job.
I’m left with a little puzzle now. Friend seems so familiar — a brother, maybe, or someone’s boarding-school boyfriend, the tall one with the mordant sense of humor. Many of the emotional patterns he describes in his parents and grandparents are familiar. I already knew that much of the cultural and physical baggage of my life is stereotypically WASP. Could that background really exert such a strong influence on relationships, too? I thought I was pretty highly evolved, but every now and then he wrote something that flew like an arrow through a chink in armor I thought I’d long ago left off. For instance, once he is well launched on a relationship, he can’t believe his good fortune. But “[p]erversely, still I sometimes felt the sadness of happiness, of no longer having to fight to prove I was worthwhile.”
Friend also addresses the fact that our caste is dying out. The clubbiness and insulation of our parents’ generation has thinned to nothing for our children. Pretty hard to avoid that nostalgia, after all.