This is an incredibly difficult book to rate as it is written well (the author doesn't write for The New Yorker for no reason), but the subject itself was at times tedious.
Tad Friend is a self-proclaimed WASP from a long lineage of WASPs, and is at once both disturbed by and proud of it. His memoir discusses what it means to be a WASP (not to be confused with a "prep" which is detailed in one of the chapters), and the first half of the book that investigates this lifestyle is fairly interesting as it always is to see how other folks live. But once Friend began delving into his place in the family, his views on his family, his own beliefs (which don't vary that much from his family, despite what he seems to want to portray), etc. my interest waned. After a while it felt like he was that person at the office who always complains about the amount of work he/she has to do, but as soon as the boss takes away said amount of work, he/she takes it all very personally, he/she didn't really want it to go away for all of his/her bitching. Friend does that here in some ways in that he almost turns his nose up at the lifestyle of his family, and complains about the lack of love and other necessities, but then turns around and embraces those exact things.
I guess that's probably his point. We are what we know, after all.
Moving beyond that, the second half of the book felt like a vehicle for the psychoanalysis he eventually stopped participating in, which he describes in some detail. The book is his way of continuing his investigation into his own behaviors, though I'm not sure in the end he made any true headway. After all, he just wants to be loved, despite where he came from.
There were some nice shout-outs to Pittsburgh, particularly Squirrel Hill (the family compound originally was on Solway Street). It's a shame it no longer stands there; I would have liked to see it outside of the b/w photo in the insert.
What complicates the rating system for me is that it's all written well, which I can at least respect. His words smelled of all of the Henry James, Edith Wharton, Scott Fitzgerald high-society novels I've ever read, and Friend makes sure to acknowledge that throughout his memoir. Those authors made money on these situations because they were real, which Friend illustrates wonderfully here, whether I approve of the lifestyle or even can fully comprehend it. No family is without flaws, certainly, and Friend gave me a fine serving of food-for-thought. I just wish it hadn't been quite so woe-is-me-aren't-we-awesome.