Lipsyte’s last novel, Home Land, was rejected by U.S. publishers, found a home and overwhelming acclaim in the U.K., and then came back with a vengeance on our shores. That story, along with Lipsyte’s uncanny ability to make every single line either bitterly funny or bitterly devastating, made the novel a cult favorite with a Yankee Hotel Foxtrot–type cachet. Readers found a hero in Home Land’s narrator, Lewis “Teabag” Miner, who fires off withering letters to his high-school alumni newsletter.
Though the protagonist of Lipsyte’s newest, The Ask, is named Milo Burke, it’s not hard to spot Teabag’s DNA. Burke is just a little older and plumper, but he possesses that same acid tongue behind loose lips. At the outset, Milo is canned from his job in the “Mediocre University” development office, where he was tasked with tracking down “asks”—rich alumni and parents willing to donate to the school. He largely failed at that task, and said enough wrong things to the wrong people to eventually scuttle him.
But no sooner has he grown half a beard than the school asks him back because an old college friend—the obnoxiously rich Purdy—has volunteered a donation on the condition he works exclusively through Milo. The long, painful string attached is that Milo must run an errand for Purdy, which ends up dosing the book with dramatic melancholy beyond the sad-sack, midlife, nachos-get-more-love-than-me existence Milo has buffed out.
Lipsyte is one of the funniest novelists working. Describing his tendency to black out when drunk, Milo says, “My overhooched evenings tended to expire with a lone ax stroke to the motherboard.” But the question has always been whether his stories could become greater than the sum of their jokes: Home Land was hilarious and perceptive but fizzled on a flattened arc. The Ask asks more of Lipsyte and readers, and both are better for it.