The Contributions of The Ask

Sam Lipsyte
The Ask
(Farrar, Straus and Giroux)

"I'm not very likeable, am I?"
"You're likeable enough," said Vargina.
"No, I mean if I were the protagonist of a book or a movie, it would be hard to like me, to identify with me, right?"
"I would never read a book like that, Milo. I can't think of anyone who would. There's no reason for it."

Meet Milo Burke, protagonist of the novel The Ask by Sam Lipsyte. He's like many of us in the office, a lost soul, a husk of his former self gravitating to the company of those whose lives seem fulfilled, or at least filled. Milo's job is in university donations, to ask for money. He is terrible at it, as he is at most things, and his entire deal goes to shit.

This may sound like a thousand other cubicle idylls that came out after disaffected emasculated office drones by the herd saw Office Space and thought, "I should do that!" - I wrote at least an outline of a sci-fi novel where the office gets destroyed -  but the difference is those other books are not wrought from Sam Lipsyte's wit, not drawn from the inkwell of his contempt, not etched with his acidic humor, and ultimately not as honest. The Ask erodes any and all pity from self-pity to expose the self, frail and ill-equipped for the fight as it may be, and makes it fight. Failures are as flimsy as triumphs in The Ask; the contours of life's richness are maintained by dreams.

A donut vendor relates this doozy to Milo in the park:

"Was it the one where you're inside the girl and you are pumping her and pumping her and you're so happy but then it turns out it's not a girl, it's really one of those super poisonous box jellyfish, and it stings you and you are screaming and screaming and the sky rains the diarrhea of babies?"

"The...no, I don't think so."

"I get that sometimes. Anyway, see you around."

Things shift quick in The Ask, like how things shift quick in a mudslide, and causality and blame are as irrelevant as merit when the mud comes. Lipsyte's tightly coiled jokes within jokes are the only thing holding his characters, jokes themselves in one way or another, together. The Ask is one of the funniest books in recent memory, but it's a wincing kind of funny, underscoring the point when you realize slapstick is just another kind of injury.

The Ask is also one of the most shrewdly marketed books in recently memory, making the rounds of every burgeoning lit blog and online magazine, being one of the first sanctioned products of the new literary blogophere. Since outsideleft is looking to shoulder its way into that arena, I was forced to ask in this review that inevitable question that Milo and every office schlub must ask him or herself - what can I bring that's different? Unique?

I found a similar answer to Milo - connections. Milo conditionally gets his job back as a donation solicitor with a private university because an old college friend is a wealthy potential donor, one whose similar spectacular missteps in life form the exoskeleton in which Milo squirms after his situation goes to hell. The relationship volleyed between Milo and this donor (and the relationships that fall under that arc) is the hinge on which the story ultimately swings, so I  have a well-read friend who very successfully works in that exact business. She had this to say about Lipsyte's portrayal of those doing the asking:

I really enjoyed the book, although I've never met anyone in development that nearly that clever or so spectacularly neurotic.  In my experience, they tend to be either earnest, worthy types (ineffective) or preening and ego driven (effective). The earnest, worthy types wouldn't know an opportunity if it slapped them in the face, in fact they might reject it if it didn't meet their personal ethical criteria. The ego types have that psychopathic ability to ignore everything but their own interests and it's surprisingly effective as you need focus and drive to concentrate on a project and a prospect and bring it across the finish line. (Of course they are also loathsome individuals.)  Hopefully a good development officer has well developed social skills, is a bit of a superficial polymath (if that isn't too oxymoronic) and is happy to be a handmaiden to success.

Lipsyte is brutal in his take. He, like many tender souls in corporate settings, does not see the endless grid of cubicles as troops in formation but instead as field of fallen soldiers and while this romanticists eye-view is tempting, it ultimately rings a little hollow. My friend weighs in further:

The book totally lacked respect for the concept of philanthropy and the fact that it's written by an academic didn't surprise me - being cynical and world weary is the only stance they tend to see as valid, although it's obviously the laziest, least rigorous attitude imaginable. UNLESS they are totally brilliant and at the top of their fields.  Then they are usually truly classless individuals who see money and donors as lovely things that help make the world go round. It's the grasping middle that's hard to work with and who sneer at development out of jealousy and poor socialization and the knowledge that they will never be onto the big money. I'm lucky in that I decide who I'm going to work with because I can say whether or not a program is viable or not for donors, so I only choose the lovely, super successful ones to work with and we have a marvelous time.

Throughout the book Milo manages to have as bad a time as possible and perhaps that is the fate of the deeply introspective; you simply run out of things to do in there but are ill-equipped to go anywhere else. Dreams dissipate upon contact with the open air, so we need something else. While I'd suspect that Lipsyte is no fan of the corporate world, it can still be gleaned from this comedic migraine of a book that it takes a confluence of individuals to make things happen in the world - in a company, in a marriage, in friendships, in parenthood -and those confluences require constant effort, lest they fall apart at the seams, and that is where The Ask transcends its own dark humor. It may not fully embrace that interconnectivity, but it implies that one needs the ask in order to find the answer.