NARRATORS of comic novels tend to fall into two categories. Either they are jaded insiders in a world they see is a sham, or they are hapless outsiders who long to be insiders, even though they sense it is all a sham. Outsiders are harder to pull off. It takes some convincing to empathise with a true loser.


Sam Lipsyte made his name with “Home Land” (2005), a darkly funny book written as letters to an alumni newsletter. The hero was a washout—loveless, nearly friendless and all but jobless (“It’s time you knew the cold soft facts of me. I did not pan out.”). But he was also hilarious, with the incisive cruelty of a true underdog. Like “Portnoy’s Complaint”, Philip Roth’s 1969 novel, “Home Land” was less a story than a voice, vital, irrepressible and sexually perverted, just without the exploits.


“The Ask”, Mr Lipsyte’s new novel, is more ambitious. Again the narrator, Milo Burke, is a sad, cynical sack. Raised in the New Jersey suburbs and trained as a painter, he once believed that his artistic genius would make him famous. Now in his 40s, with the slovenly build of a “half-melted block of Muenster cheese”, he is embittered,  occasionally mawkish and complacent; a “man with many privileges and zero skills. What used to be called an American.”


But Milo makes do. He bumbles through his job fund-raising for an art school, and spends his nights watching television with his wife and son. His life is as reassuringly bland as his daily turkey-wrap lunch. But then he is sacked from his job and exiled to the unemployed wilds of doughnut shops and internet porn. His luck seems to change when a rich old college buddy involves him in an important potential donation to the school. Milo’s challenge is to secure the funding (the titular “ask”) without getting tied up in all the strings attached.