The Ask evoked bouts of uncontrolled laughter and wincing during my daily commutes from my apartment in Astoria to my fundraising job in Manhattan. Why all the wincing? Because Milo, Lipsyte’s lovably unlikeable protagonist, is a mediocre development officer who lives in Astoria and works in Manhattan. This book is a caricature of class, professional and neighborhood relations that skewers the conceits of every demographic it presents.

It is clear that Lipsyte admires the rare person who works hard, has clear expectations, puts forth their best. But he does not fill his book with such people. Instead we have the nebbishes, the whiners, Gen-Xers coming of age in midlife, struggling to find affordable daycare and still maintain their edge. Coddled Milennials spout profanity and expect approval, taking their ambition and paperwork home with them to chicken wire cages in old Bushwick warehouses. The unconscionable privilege of the privileged, the righteous, tragic anger of the non-privileged, and the comical failure of those who squander their privilege.

There are a lot of ideas in The Ask, and you can pick and choose from them. For the most part, Lipsyte’s rapid, wit-infused dialog makes up for in fun what it lacks in believability. Those of us steeped in Joss Wheedon-speak should have no problem with this. Milo is stomach-turning at times, I did get tired of hearing his sexual inclinations to each and every woman he encountered, but it’s forgivable. We’re rooting for him by the end. For all its wild parody this book is spot on in its characterizations, and extremely enjoyable.

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