Sam Lipsyte is the poet laureate of the American loser. If there was any question about this before, his new novel, The Ask, has settled the matter. Lipsyte is the kind of comic writer who has his finger on the pulse of the most pathetic possible way of living in America at any given time. The Ask does for the recession what The Subject Steve did for the malaise of the late ‘90s and Homeland did for aging loyal Reaganites in a post 9/11 world. It’s narrated by Milo Burke, who is a former development officer at a third-rate university only referred to as Mediocre University. Newly unemployed and unable to support his family, Milo is given one last chance at his old job: charming a potential donor—a major “ask” in development parlance—who happens to be his old college roommate. And if, in the process, Milo becomes an indentured servant tasked with covering up his old friend’s sordid past, then so be it.

Lipsyte has always excelled at a certain kind of first-person protagonist, the self-aware, self-righteous misanthrope who refuses to buy into the system. The kind of failure you can’t help but cheer for. In this sense, Milo Burke is cut from the same cloth as Teabag Miner, Homeland‘s protagonist. In fact, everything that is wonderful about Lipsyte is present in The Ask: the cripplingly hilarious dialogue and observations; the ability to find comedy in the most dismal of circumstances; the male friendships, equal parts homoerotic and homophobic; the sudden rhapsodies of beauty and despair sandwiched between assaults on the mundane and ponderous.

But in The Ask, Lipsyte’s view of America has evolved and become more complex than anything seen in his earlier novels. The rants are less myopic; resentment has turned into anger. For better or worse, Milo is aware of the systems of power that surround him. Lipsyte’s narratives have always ultimately been about class, the anxieties of a lower middle class peering in at the world of privilege that lies frustratingly beyond its reach, but this quality has never been clearer than it is in The Ask as Lipsyte focuses his considerable talent on the broken promise of a liberal arts education and the fallacy of social mobility.

The ultimate lesson of The Ask is that everything is bound to disappoint: your job, your marriage, your friends, your children, your parents, your dreams, your talent. And as the last few chapters of The Ask fail to coalesce, when the climax peters out and fails to delivers on the pay-off you’re expecting, you realize that Sam Lipsyte is bound to disappoint you as well.

But I like to think that Lipsyte meant it that way. Things don’t usually work out for the losers of the world. Satisfying conclusions are rare and hard-fought. It’s a difficult truth, but there’s no one I’d rather hear it from than Sam Lipsyte.

- Stephen Aubrey is a Brooklyn-based writer and performer.

The Ask by Sam Lipsyte, Farrar, Straus and Giroux ($25, 296 pp.)