A champion of the bitter underachiever or slacker aesthetic, Lipsyte stays true to form in his latest, “The Ask,” giving us a pudgy, not quite employed Milo Burke as narrator. Milo’s former job consisted of asking wealthy alums of “Mediocre University” to donate money. He is now brought back on a probationary status of sorts to pull in a big donation—the ask—and joins his old crew: Horace, Vargina and the boss, Dean Cooley. “People often called him War Crimes,” says Milo of Cooley. “By people, I mean Horace and I. By often, I mean twice.” That’s what readers are getting themselves into with Lipsyte, a joke with a stuttered punch line. Where most authors would be satisfied with single explanation, Lipsyte uses several, often veering toward repetitiveness though it mostly adds to the humor. He steers Milo around a world where the joke always seems to be on him, whether it’s told by Purdy, the wealthy alum, or Don, Purdy’s estranged son with the prosthetic legs romantically referred to as his “girls,” or even his own wife, Maura.
In “The Ask,” Lipsyte retains his trademark sense for perfectly embarrassing humor you feel comfortable repeating only in front of certain company, but he is doing more than writing a comedy. Sure, he throws his usual quick darts toward the silliness of the modern world: overpriced preschools, Internet porn, reality television, the war. But, as the kiddie-diddler says while discussing the time before microwaves, “No time is better than another time. It’s preposterous. There are always people doing kindnesses and there always people smearing each other into the earth.” I don’t know that it has to do with growing up, but Lipsyte allows himself to touch poignant themes of family life that may have escaped his previous efforts. The sentences still explode with whatever that force is that kids pay good money to go to school to learn but rarely do, but he’s more patient now. And, for as funny as “The Ask” is, it is also genuinely sad and honest. As Milo says, “Our lives hinge on these moments of quiet tenderness. We stand or fall on them. I passed out on mine.” (Peter Cavanaugh)
By Sam Lipsyte
Farrar, Straus and Giroux, 304 pages, $25