If you’ve heard anything about Sam Lipsyte, you’ve probably heard that he’s funny. Scabrously, deliriously, piss-yourself funny (his characters would no doubt find a dirtier, and funnier, way of putting it), drawing audible snorts even from the kind of people, such as the people in his novels, who are way too cool to laugh out loud. In three previous books of fiction, Lipsyte has established himself as the poet laureate of overeducated American loserdom, celebrating the putatively more honest inner lives of those who, in the words of Lewis Miner, the lovably skuzzy narrator of his second novel, the cult hit Home Land (2004), “did not pan out.”
Lipsyte’s characters, crucially, are guys—specifically, the kind of smart-mouthed, vaguely artistic, no longer quite young guys who went to good colleges but are still living in the basement of the culture, bingeing on junk food, junk TV, and self-abuse, with few marketable skills beyond the knack for folding every synaptic twitch into a mini-aria of rage, resentment, and oddly cheerful self-loathing. The Lipsyte hero is a washout who has got the culture’s number, or thinks he does, finding in his own failure an unavoidable corruption and decline at the heart of things. As Miner declares in Home Land, “Our nation wallows in the dark too much, eating cheese puffs, touching ourselves. We think we’re not fat and that we’re a nation.” Milo Burke, the thirty-nine-year-old narrator of The Ask, Lipsyte’s sneakily poignant third novel, has a similar worldview and a straighter way of getting to the point. “Why was I such a diseased fuck?” he asks himself. “It had to be society’s fault. I loved people, all people, except for the ones with money and free time.”
At the beginning of The Ask, Milo is fired from his job in arts fund-raising at what he likes to call “the Mediocre University at New York City,” the kind of place where “people paid vast sums so their spawn could take hard drugs in suitable company, draw from life on their laptops, do radical things with video cameras and caulk.” A formerly promising painting major with a degree from what we’re given to understand was a less mediocre school, Milo lives on the fringes of the creative class in Astoria, Queens, with his wife, Maura, and their three-year-old son Bernie. He spends his days eating doughnuts, cruising niche porn sites, and wondering where Bernie picked up words like “depressive” and “pansy,” and what they might have to do with him. Maura works part-time at a marketing firm, writing memos on “need creation” and possibly having an office affair on the side. They have stopped having sex, and pretty much stopped talking. Watching a cheesy romantic comedy one night, Milo reminds Maura, “We used to hate this together.” She replies, “Maybe we…
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