Sam Lipsyte’s “The Ask”

7.5/10 dropps

Sam Lipsyte’s funny, self-deprecating antihero Milo Burke is the center of the 2010 New York Times notable book of the year, The Ask. Milo, father to a precocious little boy named Bernie and the other half to a straying wife, is a failed (for a lack of trying) artist who works in the cutthroat financing department at a largely under-funded, fictional arts institute in Manhattan. At the school, Milo’s job (one at which he is not particularly skilled) is to ask wealthy alumni, students’ parents, and known socialites for donations towards new facilities and equipment. His life goes into a tailspin when he gets the axe for yelling at and calling talentless the daughter of a potential donor.

Apart from Milo’s personal plight in the book, Lipsyte clearly chose to render The Ask as a social commentary that touches on the perceived value (or lack thereof) of arts education in America, as well as the bureaucratic messiness that so frequently plagues the various departments at institutes of higher education. Part of what seems to keep Milo so on edge about his workplace situation is the comically hot-and-cold demeanor of his boss, whose wavering attitude is largely reflective of the ones that higher-ups all across America have necessarily adopted in these times of economic crisis, where employee and departmental fates are most uncertain. At one point in the book, at a staff meeting, Milo’s boss announces that pretty much everyone in the department will be cut, despite the fact that five minutes prior, they all celebrated a giant donation.

After Milo gets fired, his would-be saving grace arrives in the form of a rich, former art school friend named Purdy who offers to donate a large sum of money to the institute where Milo works (and in effect, get Milo his job back), as long as Milo is willing to help him with some personal business. As it turns out, though Purdy has become a wildly successful businessman, his past has come back to haunt him in the form of a vengeful, illegitimate son, Don, who lost his legs serving in the Middle East conflicts. Don has been extorting money from Purdy, holding it over Purdy’s head that he will reveal himself to Purdy’s real family if he doesn’t comply with the requests. Milo’s difficult feat in the matter becomes to assuage Don and convince him to take one final payout and just go away.

Over the course of The Ask, Lipsyte introduces a cast of hilarious characters including Milo’s earthy, newly-lesbian mother, an annoyingly funny office boy named Horace, and a now-homeless, former donut shop owner. Each character, in one way or another, plays off of Milo’s neuroses or causes him to have to reflect on his current circumstances. Don is perhaps one of the most influential of these to help Milo subversively understand that things could be much, much worse.

Told both in real-time and in flashbacks to Milo’s childhood and art school days, The Ask is a biting, satirical product of America’s current climate. It follows the average Joe prototype through the ins and outs of corporate America, workplace politics, a stale marriage, and one ridiculously contrived progressive preschool. Crack open Lipsyte’s The Ask in order to find out if proverbial everyman Milo has what it takes to make it through.

-Emily Simpson