The Ask

Sam Lipsyte wants you to shit your pants. By that I mean parts of The Ask are so sphincter-looseningly funny that you will want to invest in some adult undergarments before reading it. As the author of several previous novels, including the Believer Book Award–winning Home Land, Lipsyte has cultivated a well-earned reputation as our preeminent chronicler of the absurd. There isn’t a funnier author working today. But what makes The Ask so incredible is that the delightfully nasty jokes, puns, and malapropisms—and they are delightfully nasty—serve the development of the characters and a plot that isn’t all that riotous. There’s a serious story here and this is a novel of real maturity, albeit one that routinely employs words like “dick-smacked” and “spidercunt.”

Milo Burke is a frustrated former painter who, thanks to a sexual harassment accusation, loses his job in the fundraising office of a New York City school he calls “Mediocre University.” That’s just the start of his troubles. Milo has reason to doubt his wife Maura’s fidelity and his own three-year-old son, Bernie, thinks he’s a “pansy.” He’s desperate for work when his former boss, Vargina, recruits him to land a big “ask” from a particular potential donor. “An ask,” Milo explains, “could be a person, or what we wanted from that person,” but in this case it’s also an old college friend, Purdy, who struck it rich during the Internet boom.

To win his job back and possibly save his marriage, Milo has to woo the increasingly eccentric Purdy into donating a serious amount of cash to the school. Before you can say, “That sounds like the makings of aVinceVaughn movie,” the plot thickens. Purdy has a grown son, a Gulf War vet named Don, whom he doesn’t want his wife to know about. He sends Milo to deliver hush money and soon Milo’s professional and personal lives—both of which are clearly in rough shape—come crashing together. There’s also an ideological schism among the staff of Bernie’s experimental preschool and, of course, tension at home with Maura.

The impressive thing about The Ask is that all characters are so fully realized, even the minor ones who don’t stick around on the page for very long. Lipsyte has amazing powers of observation and the talent to put the ineffable—and uncomfortable—into words. People like the “kiddie-diddler” who hangs out at Milo’s favorite doughnut...