This is a fun & funny novel, an intelligent satire on contemporary times that still manages to say something serious in spite of all its exaggeration and slapstick. Milo Burke is a failed painter of middling talent with still lingering fantasies of artistic grandeur. Instead of art world mega-celebrity, he's stuck in a bourgeoisie life with an uninterested wife, a time-consuming kid, and a desultory job at a third-rate university. He works in "development." What's that mean? He's one of those guys who calls up super-wealthy people who might want to ease their conscience or, more likely, inflate their ego by making an endowment to higher education, in particular, that endangered branch of it known as "the liberal arts." By the end of the first chapter, Milo manages to get himself fired by losing his cool & insulting the wrong student, the spoiled daughter of one of the school's more influential patrons. But no sooner is chapter two over when he gets an unexpected chance to redeem himself. An old friend from Milo's own college days, the scion of a wealthy family, is thinking of making a big bequest—a "give"—but on one condition: that Milo do "the ask."
And so Milo is back on the case, in a probationary capacity, but as it turns out there's more to what his old friend wants than merely a chance to be charitable. There's an illegitimate child involved, now grown into a disgruntled, disabled Iraqi war veteran who's making not-so-veiled threats to emerge from the shadows and spoil daddy's new life. For Milo, there are old grudges to settle: there is infidelity, there are issues with his dead, no-good philanderer of a father, his very-much-alive lesbian libertine mother, and his diabolically cute, but preciously cruel four-year-old son. As if that doesn't fill the plate, there's also Milo's donut addiction; his not-quite-but-pretty damn-close-to-it substance abuse problem, his porn problem, his anger issues, his resentment issues, and, of course, now there are his money-shortage and unemployment issues. Milo, in other words, is in desperate straits.
As noted, Lipsyte is a very funny writer. So funny he can't seem to help tacking on a lot of scenes that aren't really necessary to advance the story but serve as comic set-pieces for no other discernible purpose than to show off how funny he is. But you don't mind the superfluity so much because, well, as now noted twice already, he's really funny. His comic timing is syntactically flawless. The pages dissolve on your eyes like an ocular version of whipped cream. You're done before you know it…not quite full, but momentarily satisfied. It's not Schopenhauer or Foucault but Lipsyte writes as if he's read those guys and as if he trusts that there's a good possibility you may have read those guys, too. Or seen their books lying around at a friend's house. Or at least heard their names mentioned in passing during a lecture you weren't paying any attention to. In short, he's not afraid of insulting your intelligence by assuming you have any or losing your attention by writing as if you're not a total moron.
Here's something he says towards the end of the book—a little bit of heartfelt, practical philosophy in the midst of all the madcap humor—that's particularly apt for our "terrorist times," a bracing antidote to all that "freedom-isn't-free-so-get-your-legs-blown-off- for-the-stars-and-stripes" bullshit so popular nowadays:
Here's what you need to know: The boy can walk away from the ogre's castle. He doesn't have to knock. Some people will tell you that it's better the boy get hurt or even die than never know whether he could have defeated the ogre and won the ogre's treasure. But those are the people who tell us stories to keep us slaves.
For those who think the point of life is to hoard as much of the pie as possible and everyone else be damned—and who among us hasn't been subjected to this message, practically the state religion of capitalism—he offers this counter-intuitive advice:
Squander it. Always squander it. Give it all away. Whatever it is. Squander it. Don't save a little part of you inside yourself. Not even a scrap. It gets tainted in there. It rots.
Bonus points to Lipsyte for writing a novel about a father's love for his four-year-old son that doesn't turn into emotional slush. For writing about a hapless white male without turning him into a total schlemiel. Milo is as clueless and ineffectual as any Woody Allen schmo, but he's also got some fight in him still, some redemptive, righteous bitterness, and a core of integrity that keeps him from being a total kickball. Kudos, too, for writing on that tightrope between sarcasm and sentimentality, which requires courage, skill, and discipline; courage not to deny sentiment entirely and become coldly cynical—after all, we're sentimental creatures; skill and discipline which are both necessary to maintain one's balance and avoid the temptation to abandon oneself to the bottomless abyss of bathos. And, finally, props for ending "The Ask" not with a cloying "love me please" whimper but, quite literally, a bang.
If nothing else, Lipsyte proves that the lost art of writing a deadly serious comic novel for a widespread audience is not entirely lost. "The Ask" is subversion and diversion for the vanguard of the masses, pointed cultural critique and low comedy in one happy-go-lucky package, not-quite-mindless entertainment for the slumming revolutionary of the quietest—and most effective—revolution of all: the one that takes place between your ears.