Sam Lipsyte’s The Ask: the Disgust and the Pity

Sam Lipsyte’s The Ask will probably long remain the funniest and best novel filed under this Library of Congress Cataloging-in-Publication data:

1.  College administrators– Fiction.  2.  College benefactors — Fiction.  3.  Education fund raising — Fiction.

Because god forbid this cheapskate thrifty consumer should actually buy a new hardback book (sorry, Sam), I first read his previous novel Home Land while I was waiting for this one to come from the library.  They have a lot in common, to the point that Home Land feels a bit like a first run at this one (which is deeper and more emotionally nuanced, though Home Land is also hilarious).  The narrator/protagonist of both is a similar character, a middle-aged (39 in The Ask, a bit younger in Home Land I believe) middle-class fuck-up confronting his own failure (in career, friendship, love, sex) and the success of his former friends and classmates.  In both novels the guy struggles with an educational institution — in Home Land he’s trying to submit class notes for his high school alumni newsletter; in The Ask he’s in effect graduated such that he dwells on his college days and is trying to keep his job as a fund-raiser for Mediocre University of New York City.

Lipsyte is just a very very funny writer.  I’ll share two of my favorite passages in The Ask. Here he describes his wildly-successful former college buddy Purdy who made a fortune with some kind of 1990s tech/internet music enterprise.

Still, he had been ahead of his time with his online music outfit.  It might sound ridiculous now, but he had been one of the first to predict that people really only wanted to be alone and scratching themselves and smelling their fingers and staring and screens and firing off sequences of virulent gibberish at other deliquescing life-forms.  So for us he provided new music and photographs of fabulous people making and listening to the new music, as well as little comment boxes for the lonely, finger-smelling people to comment on the looks and clothing of the fabulous people…

That captures the tone and worldview pretty well.  A Confederacy of Dunces came to mind for me; there’s a similarly disgusted, hilarious bile directed at contemporary culture.   This passage is also typical in its seething jealousy — Lipsyte is a poet of self-hating envy.  Milo hates and resents Purdy for being a winner in such a corrupt, crappy, stupid game, and he can’t break out of his self-destructive spiral of envy/self-hatred/self-pity/rage.

It also struck me that The Ask is oddly similar to Man Gone Down by Michael Thomas.  Screw-up artist father in contemporary Brooklyn, trying to hang on to his shaky marriage and to be a good father despite himself; encounters with successful friends from long ago; somewhat desperate unemployment leading to bouts of last-ditch manual labor.  The tone is 180 degrees different — Man Gone Down isn’t funny in the least (I kind of admired it but actually didn’t finish it) — and the vector of sociological analysis is all different too.  Man Gone Down is about an African-American (half white) man in a world of white privilege; The Ask is about a white man “of many privileges and zero skills” who played his cards slightly wrong (he intended to be a painter) and is on the verge of falling out of the middle class entirely.

Here’s another passage that cracked me up.  Milo, with his 3-year-old son (the novel’s very funny on parenting, daycare, etc), is having a coffee with the mother of another kid.  He thinks they’re flirting heavily, and he’s decided he doesn’t have it in him to cheat on his wife, so he’s going to disappoint the woman by pulling back.  Then she mentions her boyfriend.


I watched her face register what I, and only I, it turned out, had been mulling, saw the surprise there, the disgust, the deeper disgust, the moral judgment, the slight flattery, the steepening dive into new realms of physical revulsion, followed by pity’s steadying hand.

So hilarious.  “Pity’s steadying hand” killed me.  In post-college days Lipsyte was the cape-wearing singer of a sort-of grunge band called Dung Beetle, singing under the name Sam Shit.  There’s definitely something rock-and-roll and improvised-feeling in the novel’s wildly creative and obscene invective — Milo and Lipsyte could be what Sam Shit turned into — but the writing is also very precise and exact.  This passage captures the self-pity and disgust that well up out of the narration.  Lipsyte’s protagonists have a bit of a hangup about the physical ideal embodied by preppy WASPs; the novels are partly about being white and privileged but not quite privileged enough or as much as it seemed back in college, not secure or coolly confident in one’s privilege, not handsome, not fully in control of one’s body, emotions, life or career.  (Can’t find the line now but at some point someone says to Milo something like: 400 years of white male privilege and you can’t do any better than this?)

Home Land is pretty amazing as surreal satire — witness for example the Kid, the world’s champion masturbator, who makes dream-like appearances as a wandering cowboy sage continually pondering the question, “how much whang can a man spank?”  But The Ask goes deeper and is both uproarious, affecting, and pretty unsettling — it’s really fricking bleak.

Here’s an interview.… And a good Jennifer Scheusler NYRB review.  And the A.O. Scott think piece linking The Ask to Hot Tub Time Machine (he totally has a point, actually).