Sam Lipsyte, the Wodehouse of our meritocratic world.

We walk the halls of Barnes & Noble, lost, pale, and discontent. Surrounded by rows and rows of Nice Writing, we search in vain for a novel that will make us laugh. We gaze fondly at the Amises, remember our dear friend Bonfiglioli, reread the best passages of Scoop and A Handful of Dust, salute Joseph Heller, give Vonnegut a friendly page riffle, and end up where we always do. Right ho, Jeeves.

Might I suggest a new place to stop? The collected works of Sam Lipsyte. Over the course of two novels and a short story collection, Lipsyte has become a fine microbrewer of bitterness. He's also an apt writer for our meritocratic moment. In America, we labor under the delusion that if we were all just a little more highly effective, a little more focused, we could ascend into a realm of first-class check-in, enviable real estate, and unruffled contentment. And should we fail? Well, that's your fault now, isn't it?

Lipsyte's heroes are not well-rounded; they are the gnarled apples left on the tree. They say the wrong things, choose the wrong paths, own a lame cell phone, and eat the wrong food. But they have a semblance of integrity and the freewheeling wisdom of the loser.

The outer borough Socrates of Lipsyte's new novel, The Ask, is Milo Burke. As a reviewer, I will describe him as a development officer at a university in New York that aspires to be more prestigious. In Lipsyte-speak, Milo is "one of those mistakes you sometimes find in an office," hired to "grovel for more money" for an institution where "people paid vast sums of money so their progeny could take hard drugs in suitable company." Milo has a "good shitty job."

Milo loses that job but gets the chance to win it back when a mysterious "ask" surfaces. As Milo explains: "An ask could be a person, or what we wanted from that person. If they gave it to us that was a give." The ask is an old friend from Milo's bright college years, Purdy Stuart, who was "one of the first to predict that people really only wanted to be alone and scratching themselves and smelling their fingers and staring at screens and firing off sequences of virulent gibberish at other deliquescing life-forms." Now a successful Internet entrepreneur, Purdy is prepared to give a major give to the university, with one condition being that the recently-fired-in-shame Milo handle the negotiations. Purdy, among other oddities, has a penchant for collecting old college friends.

As Milo and Purdy reconnect, the novel details how their two roads diverged after the groves of academe. At school, Purdy was one of those enigmatic, self-possessed types who could fit in with all the other types. On weekends, he would "disappear with the children of the super-rich" but also spend late nights smoking bowls with Milo and his faux-bohemian housemates. Now rich and successful, Purdy senses that he has become faintly ridiculous, something of a hollow man. Witness the moment when he calls Milo from an ideas conference in Vail, Colo., and declares: "Do you realize that someday we will be heating our houses with trout?" But Purdy also understands the iron logic of money, how to leverage wealth to bend the world his way. He's very effective, curiously nostalgic.

Meanwhile, Milo's existence in Queens, N.Y., is a tepid bath of self-loathing. In the mornings, he drops his son Bernie off at an intense preschool where he is referred to only as "Bernie's dad" so as to "maintain contextual integrity for the other children." Alone during the day, he rails against "the me's"—the people like him—who "were going to wreck everything, hike rents, demand better salads" in his gentrifying neighborhood. Yet he's also annoyed by the slowpoke immigrants on line at the post office: "Don't you worry your behavior will reduce me to generalizations about why your lands are historically fucked?" Milo's rage is all-terrain—he cannot control his environment with wealth like Purdy, so he takes the consolation prize and ceaselessly mocks and analyzes everything around him.

Including himself. And this is where Lipsyte slips in the previously mentioned wisdom of loserdom. Milo's convinced that he can't find a better job because he has the "old brain": "Jobs weren't about experience anymore, just wiring." Though Lipsyte is not so obvious or pat, Milo's bumbling, his lack of mental control, comes off as a more honest and deeply felt way to live than Purdy's. Money lets you have blind spots.

In Lipsyte's past work, he's been hampered by an inability to write a simple sentence without a pun, a play on words, a delicately rendered sexual fantasy, or a tasteless metaphor.   In The Ask, Lipsyte eases back on the throttle and reaches for something more than a sentence that produces a knowing chuckle. An episode in which Milo remembers a neighborhood family that died in a car crash comes close to open-faced pathos. We also learn that Purdy has an illegitimate son, Don, who has returned from Iraq without his legs. This character gives Lipsyte the chance to rail against war in—believe me—a rather subtle, profanity-laced, bigoted, racist way.

Lipsyte's usual dartlike details abound in The Ask. Who among us has not taken a "hot, khaki-moistening" walk along a busy boulevard? He also has a knack for presenting grander statements in an undercutting way that's not insufferable. Like this attempt to define a generation: "We were stuck between meanings. Or we were the last dribbles of something. It was hard to figure. The fall of the Soviet Union, this was, the death of analog. The beginning of aggressively marketed nachos." Here's the old Gen-X posture, the permanent in-betweenness, but presented without the deadly lack of humor.