The Loser Chronicles

Photo: Ceridwen Morris; Illustration: Charlotte Strick

You schmoes of America, rally ’round your bard! You sad sacks in sweaters, undershirts untucked and dangling below your belts! You frustrated artists, you terrified fathers: Do not be ashamed of your increasing girth, your outré sexual fantasies, your rampant neck-beard. One lonely man sings your song. His name is Sam Lipsyte, and right now he is eating a jelly doughnut.

We’re in a greasy spoon in Astoria, a model for the doughnut shop haunted by Milo Burke, the downsized, disheveled hero of Lipsyte’s new novel, The Ask. Cheated on by his wife, with no desire to return home, Milo perches on a stool at the doughnut shop late at night, picturing himself as the lonely diner in Nighthawks. (The Hopper painting is part of the rich tradition of American zhlubhood that Lipsyte’s novels celebrate.) “I’d always studied it from the artist’s perspective, the stark play of shadow and light,” failed painter Milo says of Nighthawks. “But to be the fucker on the stool was another kind of stark entirely.”

Lipsyte eats the doughnut as daintily as he can, but powdered sugar still dusts his beard. A corona of messy brown hair frames a broad face; his eyes hide behind chunky black glasses. There’s no way around it: Sam Lipsyte looks like a Sam Lipsyte character. But he doesn’t act like one. His narrators are rueful and bitter, like Milo, who is fired from his job as a university development officer after an outburst at a rude and wealthy art student is deemed “hate speech.” (“I think it probably was hate speech,” Milo muses. “I really fucking hated that girl.”) Or like Lewis Miner, better known as Teabag, whose scabrous, ornate updates to his high-school alumni bulletin made Lipsyte’s previous novel, Home Land—initially rejected by 35 publishers—a cult hit, the novel most likely to be thrust upon you by hipper, funnier friends.

Lipsyte, on the other hand, is kind and accommodating in person. Is the 41-year-old not gripped by the same terrors as his characters, outraged by the same outrages? “I try to leave it all on the page,” he says and finishes his doughnut.

The Ask was born from the stark language of educational fund-raising. (Lipsyte teaches at Columbia.) “An ask could be a person,” Milo explains, “or what we wanted from that person. If they gave it to us, that was a give.” “It’s ruthless,” Lipsyte marvels. “If you start to frame the world that way, in terms of the ask and the give—that kind of bare-bones approach to social interaction—it branches out into other aspects of our lives.”

The Ask is a novel deeply in tune with the asks and the gives of the current economy, and with a city whose boroughs are full of the walking wounded: the creative class, unemployed and semi-employed, whose lives have shrunk down to their family, their house, and their neighborhood, punctuated by brief trips to a now-alien Manhattan. “I was trying to write about how it feels to be on the margins of all the action and power and money,” Lipsyte says. “To be kind of part of it, but the furthest tentacle in a way.”

So Milo’s sojourns in Astoria are interrupted by calls from Purdy, his ask, at all hours of the day and night, summoning him to ridiculous yet weirdly plausible Manhattan locations, like a combination birthing center–spa–archery gallery (inspired by places where the author’s wife, childbirth educator Ceridwen Morris, plies her trade). Lipsyte is the Samuel Pepys of our excesses. “I don’t necessarily say, Oh, that’s an absurd manifestation of a societal trend, and then make a note, you know, Put in novel. But this stuff is just churning all the time.”

And after it churns, it comes out in the author’s supremely distinctive voice, particularly his knack for brutal curlicues of prose—extravagant linguistic flourishes that only make the lonely truths hidden inside more piercing. Lipsyte defends his anti-realist style. “That can be a strength as long as the language is good. That’s the game. If it’s not, then you look like a shithead.”

Is it exciting, every time a new book comes out, wondering if people will think you’re a shithead? “I wonder that every day,” he says gloomily. “That has nothing to do with my books. I just wake up thinking, Am I a shithead or not?

The Ask: A Novel
By Sam Lipsyte.
Farrar, Straus and Giroux. $25.

The Loser Chronicles