Sam Lipsyte, The Ask

Milo Burke was hard-wired to be a grump. Ever since his early teens, the acerbic family man and office punching bag—and hero of the third novel from New York’s Sam Lipsyte—says, “I knew what churned inside me. It was foul, viscous stuff. It wasn’t meant to be understood, but maybe collected in barrels and drained in a dead corner of our lawn.”

Adolescence is indeed a time of discovery, but most pubescent boys are busy masturbating and investigating new tufts of hair—not glumly declaring themselves “sites of teen toxicity.”

Suffice to say, Milo is unusually self-aware in this respect, and he carries this belief with him well into his thirties. The Ask is a book about how each of us manages our own baggage, chemical or otherwise: what do you do when the usual sites of meaning—marriage, children, artistic and professional success—have either slipped through your fingers, or else left you feeling as aloof and unfulfilled as ever?

And, in a particularly Generation-X twist on that theme, what happens when aloofness itself isn’t as appealing as it was 15 years ago? What happens when it finally curdles into full-blown bitterness?

We open with Milo getting unceremoniously canned from his job in the fundraising department of a local university for cursing out a particularly snot-nosed student who’s also the daughter of a big donor. (“You made his daughter doubt herself, artistically,” Milo’s boss scolds him. “He had to buy her an apartment in Copenhagen so she could heal.”) But all is strangely forgiven once an old, now-filthy-rich college buddy of Milo’s flirts with making a “give” of his own, and specifically requests that Milo be the one to broker the deal.

For its breathless first half, The Ask is fueled by jokes. Here Lipsyte works from the Wodehouse playbook of comedy, where all instances of plot are more like conduits, providing the quickest route from one quip to the next. But there’s also a darker undertow, reminiscent of early Martin Amis, in its depiction of the flailing, foul-mouthed desperation of the modern white male. Every laugh comes with an equally potent wince.

To give you an idea of the sheer amount of ammo Lipsyte is working with, here’s a snippet from Milo’s narration, while watching a string of immigrants struggle to navigate a post office line-up: “Come on, people, I thought-beamed. I’m on your side and I’m annoyed. Doesn’t that concern you? Don’t you worry your behavior will reduce me to generalizations about why your lands are historically fucked?”

Then, from the very next paragraph, at a bakery: “There was a high school boy behind the counter, maybe saving up for the video game where you gut and flay everyone in the doughnut shop and gain doughnut life points.”

Nearly every page dances like this, with Lipsyte plumbing the dullest corners of suburbia and turning up freshness every time.

As the book continues, however, that creeping sense of despair starts to take over. Milo suspects his wife of cheating on him, and his old friend of hanging out with him just to make himself feel better. (He knows for a fact his bosses still despise him.) He starts making increasingly desperate pleas to connect with the people around him, and clings to his toddler son like a life raft, frantically repeating how much he loves him. A few choice flashbacks show the seeds of Milo’s crisis being planted, back as an bright-eyed art student—the scene where he’s forced, via a miscommunication at a party, to abandon his father’s beloved Spanish dueling knife is absolutely crushing.

While there are many things it does extremely well, there are also a few choice areas in which The Ask is lacking. For one, the book feels shaggy and fundamentally shapeless; Lipsyte is like an indiscriminate leaf-blower, whipping up everything around him into whirlwinds of spectacle but leaving a mess in his wake.

It also gets distracted by the same modern-war fascination that last year derailed Lorrie Moore’s A Gate at the Stairs. Trivializing Milo’s plight compared to that of a Gulf War veteran with no legs is far too clumsy to be effective—especially since Lipsyte has just devoted so many pages to making Milo’s case in the first place.

But these aren’t enough to distract from the book’s many delights. Lipsyte’s caustic charm and supercharged language make The Ask go down easy, even if you’re sputtering with laughter or choking back tears in the process.

At his best, he works like a modern-day Yogi Berra, tossing off nuggets of off-kilter wisdom left and right. This one’s my personal favourite: “I bought an energy bar, and as I ate it a great weariness fell over me.”

Farrar, Straus & Giroux, 304 pp., $29.95, hardcover

(review also appeared in SEE Magazine, May 27, 2010)

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