The Ask by Sam Lipsyte
It isn’t long into The Ask, Sam Lipsyte’s hilarious and bleak third novel, before Milo Burke begins to suspect he is one of life’s losers. Once upon a time, in that bastion of hope and delusion called college, Milo was an aspiring painter. Fast forward a couple of decades. Milo now works in the development office of said bastion, “an expensive and strangely obscure institution, named for its syphilitic Whig founder, but we often called it, with what we considered a certain panache, Mediocre University at New York City.” In effect, he has abandoned his dreams to help delay the inevitable disappointment of another generation of arrogant, privileged dilettantes.
Milo is not particularly good at his job, but has grown accustomed to his cubicle, his turkey wraps, and the privilege of ogling the large breasts of his boss Vargina. A steady salary is also nice, aiding to support his wife and son, even if the former is possibly involved in an affair with a potentially gay coworker named Paul. Losing his job, therefore, after insulting an art student and daughter of a wealthy donor, isn’t the best thing that could have happened.
Enter Purdy Stuart, one of Milo’s college friends who has since graduated to life’s greener pastures. More accurately, Purdy was a trust-fund kid who has become a trust-fund adult, but his trust-fund might be the ticket to a big give to Mediocre University, and Milo’s old job, if Milo will do a little favor for his old friend.
But Purdy has an ask of his own. On the verge of fatherhood with his “generically beautiful” wife, Purdy is being blackmailed by a son he has only recently learned about, a bitter, sporadically sympathetic veteran with artificial legs, recently back from Iraq. Purdy wants Milo to get a feel for this Don Charboneau, see what it is he might want -- or take to go away, now that Purdy’s wife is “kind of into the whole trust thing.”
Milo delivers money to Don and his girlfriend, and in the process adds his own name to Purdy’s payroll. Perhaps seeing they have this in common, Milo finds a kindred, if beligerent, spirit in Don Charboneau, a man whose disappointments and status more closely resemble his own. Don isn’t the most likeable fellow, asking Milo to relay a message to his father: “that the son he cares about so deeply...hopes that someday soon he, Purdy, goes for a check-up and the doctor tells him he’s dying of cock cancer, and then he, my wonderful father, goes out into the street, stunned by the news, and gets hit by a bus, and lives only to spend the entire following year rotting from cock cancer and in horrible pain from getting just crushed by that bus, one of those huge kinds with the accordion middle, and him just begging for somebody to feed his mouth a gun.” Yet this is the same man who refers jokingly to his titanium legs as “the girls” and speaks, to Milo’s amusement as well as mine, of something called “the fake Internet.” With Don as well as Purdy, Lipsyte shows his light touch while wielding menace in the same hand.
The Ask blends humor and darkness as if they were a flavor combination so obvious, like chocolate and peanut butter, one can hardly imagine those who would prefer them separate. Much of the humor is in the prose, and in Milo’s perceptive, self-deprecating appraisal of the world, of spandexed men on unicycles and the rectal bristles of the obscenely rich. In its observational humor and precisely turned phrases, not to mention the tone of imminent resignation, The Ask recalls The Mysteries of Pittsburgh and Wonder Boys, two Michael Chabon novels whose narrators have no idea what or who will make them happy.
After an aborted attempt at flirtation with the mother of his son’s playmate, Milo decides that yes, he does want to be with his wife Maura, and the epiphany feels both genuine and completely wrong. During none of their interaction do Milo and Maura seem capable of working through their rough patch -- Maura’s term -- and if they do, nothing suggests they ever have been happy. This is partly due to the lack of scenes conveying a happy couple, save a blurry glimpse or two in flashback. Maura isn’t detestable, but aside from scenes depicting her as a good mother, she doesn’t give Milo, or the reader, much reason to hope they can make it work. But after a while, this seems to be the point.
It isn’t giving too much away to say things unravel, and more for some than others. In another writer’s hands, The Ask might be one of the most depressing novels of the last quarter century. Lipsyte’s comic touch notwithstanding, readers might want to check their hope at the door. A novel that so accurately reflects the war-torn, financially strapped era in which we live, one can safely assume, won’t end with a wedding. In life, Milo comes to see -- or finally accept -- there are winners and losers. What distinguishes The Ask from other works in the cannon of recession literature is its humor, which manages not to hide but illuminate the dreariness.
And I’ll now apologize for burying my lead: Don’t worry about what happens in The Ask. Things do happen -- meaningful, exciting, heartbreaking things. There is a finely crafted, socially relevant, page-turning plot that is probably enough to sell the novel. What pulls the reader most swiftly from page to page, however, is colorful prose as entertaining as any potboiler. Sam Lipsyte’s sentences, like favorite songs and movies, demand to be played again. Three books into what promises to be a memorable career, one can say the same about his novels.
The Ask by Sam Lipsyte
Farrar, Straus and Giroux