The Ask: Dark Comedy, Self Pity, Death of the American Dream?

Turn to any page at random of Sam Lipsyte's darkly comic novel The Ask, and there's approximately a 99 percent chance you'll find a sentence or two that will have you guffawing, rolling your eyes in amusement or outright laughing out loud. Let's give it a try:

Pg. 33 - Yep, here we go: "The room seemed cozy and cavernous at once, the kind of place I would later describe to Maura as tastefully lit. A few bourbons, and so was I."
Pg. 69 - Aha! "'I know you think I'm homophobic, but I'm not. You're the one who betrayed all your gay friends by having a baby."
Pg. 147 - Again: "It meant not much. Physical bravery probably held the same value in our milieu as skill at parallel parking: A useful quirk."

Amidst all this wit is a rather inventive plot. Milo Burke works in the development office in a crappy NYC liberal arts college, a job from which he is promptly fired in the first chapter of the novel for balling out a rich donor's daughter. Milo is coasting through a boring marriage the only joy of which is his four-year-old son Bernie. When his now-filthy-rich college friend Purdy offers a significant give to Milo's college, but only if Milo be put in charge of "the ask," Milo is re-recruited to his job. Also, Purdy has a secret problem, which he hopes Milo will help him resolve. Will Milo succeed for once in his miserable, self-pitiful life?

Two characteristics of this novel stuck out for me, besides the humore: 1) It's much less successful when it tries to be profound and serious, which it does over the course of the second half, as Milo's life and marriage careen southward, and 2) The peripheral characters in this novel are much more interesting than its main characters Milo and Purdy.

You may notice that the three quotes above are all in the first half of the novel. That's not an accident. The turn-to-any-page-experiment actually on works in the first 150 pages or so. The second half of the novel is sad. Milo turns from lovable loser to just loser. And the quirky dialogue, snappy turn-of-phrase and hilariously observed observations largely disappear to be replaced by supposed profundities and appeals for sympathy that sort of fall flat.

Thankfully, the supporting cast, Milo's mid-20s co-worker Horace, and Purdy's secret son, Don, rescue the novel. Horace opens the novel by proclaiming that America is a rundown, demented pimp. He's the hilarious counterbalance to Milo's sad wussiness. Don, an Iraq vet who lost his legs to a bomb, is angry. But he's also glib and sarcastic, with quite the "don't give a shit" attitude. He gets the best lines in the novel. For instance, Don tells Milo that "Arab men are attracted to me. They have a whole different take on buttly rapaciousness over there." So, just when you're starting to get annoyed over Milo and Purdy's sobfests, Horance or Don will show up, steal a scene, and make you remember what a fantastically funny writer Lipsyte is.

Overall, 3.5 stars for The Ask. I'm a sucker for good funny writing, and Lipsyte's sense of humor closely matches my own. For the first half of the book, I was envisioning writing an absolute gushfest and proclaiming it my favorite book of the year. But the tail end sort of put a damper on that. Still, though, it's a fun book. I'd recommend it to fans of Jonathan Tropper, Gary Shteyngart and Jess Walter.