He’s not fucking around anymore. Robert Reynolds

Sam Lipsyte's second novel, Home Land, tells the story of Lewis Miner, a loser who writes hateful screeds to his high-school alumni newsletter for perceived injustices committed against him 10 years ago, long after everyone else has forgotten them. That Miner's all-consuming plan to get revenge is pathetic and myopic doesn't matter; his voice is too goddamned beautiful. "Once more I stuff my heart into the firing tube of language, loft it into the void. See the wet meat soar?" Lipsyte writes dry, witty lines that incite eruptions of laughter just nanoseconds before the realization that he is writing nasty things about something the reader loves—by then, it's too late to get offended.

Home Land (and Venus Drive, Lipsyte's collection of stories, and his first novel, The Subject Steve, a book about a man literally dying of boredom) won the hearts and minds of thousands of readers with humor and gorgeous sentences—for what it's worth, Home Land won the first-ever Believer Book Award from the brainy literary magazine in 2005. His new novel, The Ask, is not so much a continuation of Lipsyte's twin themes of humor and self-loathing as a deepening, a maturation of both writerly skill and authorial stakes; Lipsyte isn't fucking around anymore.

The Ask is about Milo Burke, a development officer at an inconsequential New York university. When he unleashes a tirade on a self-entitled student named McKenzie—a rant so foul that Burke never reveals it to the reader—he is out of a job. Except for one hitch: A former classmate of Burke's, a wealthy dot-com magnate named Purdy Stuart, is dangling a huge donation in front of the college, and he says he'll only give it via Burke.

The Ask has made it clearer than ever before: Sam Lipsyte is the natural heir to the late Stanley Elkin, the darkly humorous novelist who is adored by just about every novelist you love. In just a single passage, Lipsyte can reenvision the internet through Stuart's shrewd, capitalist eyes:

He had been one of the first to predict that people really only wanted to be alone and scratching themselves and smelling their fingers and staring at screens and firing off sequences of virulent gibberish at other deliquescing life-forms.

Over the phone, Lipsyte acknowledges Elkin's influence: "I have been steeped in Stanley Elkin," he says. "I think his example is always looming." But he demurs on the family resemblance, saying that the only reason The Ask resembles an Elkin masterwork is because it's "the first of my books where the character's job is so central." (Elkin famously said that he didn't know where he could take a character unless he knew what that character did for a living, and he studied his main character's professions—traveling salesmen, rabbis—to gain insight into their personalities.) Then Lipsyte confesses: "I didn't even do research into how a development office would work."

Burke's devolution in The Ask is more punch-your-heart-out affecting than any of Lipsyte's previous work: This is a novel that could send readers spiraling into real depression. Unlike Home Land's Lewis Miner, Burke has a wife and a son named Bernie. And while he finds it hard to believe in anything else, his love for Bernie is something he cannot mock. He observes his son at rest:

[Children] were all lovely in sleep, but none so lovely as Bernie. Here in my humble outer-borough home a godlet took his rest, a miniature deity in need of protection until he was strong enough to fend for himself and, eventually, deliver mankind from fatal folly.

Bernie is a fabulous character, surely one of the truest child voices in contemporary fiction. When Burke tells Bernie a "saccharine bedtime saga," the son skeptically admonishes the father: "Don't forget the evil." Unlike most novelists, who don't often cite the sources for their characters and situations, Lipsyte is uncommonly honest about the source for the character: "I mean, the book is dedicated to my son for a reason," he says. "And I think that just by being his strange and beautiful self, he helped me find that voice for Bernie." This love separates Burke from the lead loser of Home Land. Miner's life is already at rock bottom, but Burke spends the whole of The Ask scrambling to keep his job, and his dignity, in order to provide for his son. That struggle gives a whole other sense of urgency to Burke's plight, and a midnight-black level of hell to which he could sink if he fails.

But Lipsyte doesn't paint a precious portrait of parenthood. In one passage, Burke imagines a dark ending to Bernie's obsessive predilection for trivia:

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Give him forty years... a beer gut, leather vest, bandana, granny glasses, and picture him the poor slob known as the Professor in a biker bar off the thruway, the arrogant but harmless turd humored for his historical factoids about extinct warrior societies and mots justes about the bankruptcy of liberal democracy, humored, that is, until some severe, silence-craving patron, maybe a thug who made his living garroting wives and business partners for high three-figure fees, suddenly didn't find the Professor's disquisitions edifying, kicked his neck in, then it wasn't so charming. Which is why I tended not to picture it.

Clearly, Lipsyte is now a man with love in his heart. Some argue that humor only works if nothing's off-limits, but that's not quite true. Adoration for another human being—the willingness to highly value another life, even if you don't value your own—gives The Ask its vibrant sense of risk, the sense that we are reading about a character with something real, something to lose. Before The Ask, Lipsyte made us laugh. Now he makes us hurt, too. recommended

Sam Lipsyte reads Thurs March 25, Neptune Coffee, 7 pm, free.