The only thing worse than working is not working
Schlubby development officer Milo Burke is fired from his university job after telling “an arrogant, talentless, daddy-damaged waif” of an art student where she can stick her paintbrush. Thrust headlong into a mid-life crisis, Milo thus embarks on a tragicomic odyssey to restore his employment status, rebuild his crumbling marriage and retain the few remaining shreds of his vanishing dignity.
The quest won’t be easy. Milo possesses abundant talent as an artist and wordsmith, but little ambition beyond the primal desire for a screw. He drifts around the boroughs of New York, torn between bourgeois comfort and bohemian dreams. He feels a vague paternalistic obligation toward his family, but mostly finds his wife and kid bothersome. He’s smart, funny, misanthropic and unemployable—every liberal-arts graduate’s nightmare scenario come true, a latter-day, recession-era Ignatius J. Reilly.
He’s also the hero of Sam Lipsyte’s amusing, occasionally frustrating new novel, The Ask, a book that probes the anxieties of the modern middle-aged man—a creature wracked with just enough guilt over his inadequacies to get off his ass and do something about them, though he begrudges the effort.
What Milo decides to do borders on DeLillo-esque absurdity: In an attempt to regain his old job, he endeavors to extract a donation from candy-addicted plutocrat Purdy Stuart, who in turn uses Milo as a manservant/intermediary between himself and his estranged, legless son, Don (who has the war in Iraq to thank for his amputation). Don and Purdy’s scenes feel less like the rest of the book’s seamless prose, and more like stilted set pieces—it’s as though A Confederacy of Dunces has suddenly shifted to White Noise, and your enjoyment of the book’s third act will depend on whether you interpret that as a compliment.
The Ask’s considerable charms lie in Milo’s hilarious internal monologues and hapless interactions with just about every other character. He maintains a poorly disguised lust for his boss, Vargina (yes, Vargina), culminating in a droll moment that finds erotic potential in egg salad. He finds himself alternately charmed and baffled by his young son Bernie, who asks such disquieting questions as, “What’s depressive?” and “What’s a pansy?” and “Do superheroes have foreskins?” Milo also endures a coarse acquaintance named Nick, who pops up to unveil the premise for Dead Man Dining, a reality show about prisoners’ last meals. And he has a love/hate relationship with his co-worker Horace, who lives in a massive space subdivided by cages. “Kids moved to the city,” Milo observes, “but there were no apartments left to rent to them, or none they could afford. But on a starting salary, or no salary, you could maybe manage a cage.”
The premise may be hyperbolic, but the threat is real—Milo can feel on his neck the hot breath of a younger generation. “I lost out to kids who lived on hummus and a misapprehension of history,” Milo says of his inability to find a new job. “Besides, there really wasn’t work for anyone. The whole work thing was over.” Here, then, is the book’s beating heart.
The Ask courses with an undercurrent of existential dread that feels acutely modern and unlikely to subside anytime soon. Bernie’s queries may get the laughs, but Milo has some questions of his own: What have I done with my life? What’s an acceptable outcome at this point? Why do I even bother? For a comic novel, the central character’s predicament is fairly bleak. Milo’s questions remain unspoken and unresolved, hanging in the air like dust particles caught in the glint of a setting sun.