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'The Ask' Puts White Collar Misery In The Cross Hairs

The Ask

Sam Lipsyte's 2004 novel Home Land took the form of one man's discursive update to his alumni newsletter — albeit one packed with more brutal, bitterly funny truth than is typical of the form. ("Let me stand on the rooftop of my reckoning and shout naught but the indisputable: I did not pan out.")

That book, which was embraced with a swift and cultlike fervor by lovers of pitch-black comedy, evinced three aspects of Lipsyte's work that emerge even sharper in his new novel, The Ask: sentences you can bounce a quarter off of; pleasantly shaggy plotting that makes only a dutiful nod toward the notion of narrative urgency; and jokes. Good ones, that land.

The Ask's Milo Burke is a frustrated husband, worried father and office drone recently let go from his position at the unremarkable New York City university where, decades before, he'd been a semipromising art student. The job he'd fallen into was one ex-semiprodigy Milo found cruelly ironic: "Our group raised funds and materials for the university's arts programs. People paid vast sums of money so that their progeny could take hard drugs in suitable company, draw from life on their laptops, do radical things with video cameras and caulk."

But soon after he's fired for insulting the fatuous daughter of a particularly wealthy university patron, the school is contacted by one of Milo's old classmates, now a powerful and ludicrously wealthy man. Milo is offered a second chance: If he can get his old friend to donate, and donate big, he can have his old job back.

You can count on Lipsyte to sculpt sentences of muscular prose loaded with solid, old-fashioned gags, and thank God for that. He's determined that the comic novel must be comical, not simply humorous. Not for him, that now-pandemic species of light, supercilious literary irony that inspires in the reader a knowing smirk. Lipsyte aims instead for the gut laugh of rueful recognition: the noise that's forced out of you upon reading a thought you're ashamed to have thought, and have never told to anyone.

Which is why, as The Ask ambles along its picaresque and circuitous pathway, you so rarely find yourself growing impatient. Lipsyte's language is beautifully crafted stuff, yes, but he employs it in service to a larger, coherent purpose that makes his many narrative digressions worth the detour. Those jokes, for example, about Milo's son's new-age daycare center, which closes suddenly one morning "due to pedagogical conflicts," are just one way The Ask sets about dissecting Lipsyte's true subject: class in America.

You feel it most keenly in the unbridgeable gap that stretches between sad, hapless Milo and his old friend Purdy, a hyperarticulate (and just plain hyper) tycoon who has replaced his cocaine habit with binges at all-night candy stores. The two men were once classmates, housemates, confidants and friends, but even as Milo gets drawn into Purdy's world of impossible wealth and embarrassing secrets, Milo remains a clumsy interloper, a born outsider.

It's biting stuff, but there's heart here, too, especially in Lipsyte's depiction of the relationship between Milo and his young son Bernie. There's heart, but not schmaltz: Again and again, Lipsyte shows Milo addressing his son as if the boy were an adorable towheaded moppet out of a '60s sitcom, only to have Bernie respond like some kind of thoughtless, self-obsessed creature completely incapable of empathy. Which is to say: like a real kid.

By the time The Ask is over, Milo will have endured much larger injuries to his already hemorrhaging self-esteem. What's singular about the novel — what inspires the laughter of rueful recognition, page after page — is the sharply observed way Lipsyte shows us a man so like our ordinary, unheroic selves: A man who doesn't so much triumph over adversity as find a way to broker a deal with it.

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Glen Weldon
Glen Weldon is a host of NPR's Pop Culture Happy Hour podcast. He reviews books, movies, comics and more for the NPR Arts Desk.