Milo Burke, the main character of Sam Lipsyte's new novel, "The Ask" (Farrar, Straus & Giroux, 296 pages, $25), works in the development office of a college in New York City, where his job is to try to raise money for the school. But he doesn't do that, or anything, well.

"I'd become one of those mistakes you sometimes find in an office, a not unpleasant but mostly unproductive presence, bobbing along on the energy tides of others, a walking reminder of somebody's error in judgment."

Ah, the glory of faking it and hoping no one notices. Such is the fate of Lipsyte's generation (X) and its particular version of angst, which Lipsyte channels perfectly in his new book even more than his last, "Home Land," a cult classic and New York Times Notable Book that had been turned down by some 30 publishers.

"Home Land" was a bitingly funny take on post-college failure, and "The Ask" is equally funny, but more infused with a bittersweetness that makes it feel real and humane. In it, Burke totes around a briefcase full of halfhearted hopes and abandoned dreams. Or is it a briefcase?

"I'd had a hard time deciding whether to carry a knapsack, a messenger bag, a canvas book bag or a briefcase," says Burke. "Each seemed to embody a particular kind of confusion and loss."

But he's getting along well enough -- married with one kid -- and holding it together until one day he snaps at the overbearing daughter of a potential donor to the university, and makes her "doubt herself, artistically."

Burke is summarily fired, but then he gets a call from the office, asking him to come in because a potential "Ask," or donor, requested him particularly. It turns out to be an old friend from college named Purdy, and here the plot thickens. What is being asked of Purdy, and of Burke, is murky at best, leading to larger questions about what we expect from others, ourselves and the world, versus what we get.

At one low point, Burke is sitting on his mom's porch with a beer bottle, "like a throttle between my legs and it seemed for a brief moment that I might be the pilot of something, something sleek and meaningful, but I was not the pilot of anything."

Nor are any of us, which is the melancholic question at the heart of "The Ask," and the dark truth into which Lipsyte looks and nonetheless finds humor, grace and a kind of love in what surely will be one of the best novels of the year. Because even though Burke may not quite grasp what it is he's driving, or where he's going, we are happy to go along with him on this fine ride called life.

Frank Bures ( is a writer based in Minneapolis.