The Ask tells the story of Milo, a failed painter working in the fundraising office of a university in Manhattan (cleverly called "Mediocre University" throughout). He has a son that he has difficulty relating to, a wife who is not attracted to him anymore, and job that he doesn't like and isn't good at. A fellow blogger who is reading the book right now said she found it kind of depressing, which I hadn't really thought about, but it's true. Milo is not a winner in this book under almost any circumstances mentioned above. In fact, one could argue that his life doesn't actually change all that much from the beginning of the book to the end. The Ask is like a more troubled version of Seinfeld, although it's just as funny.
And that's what saved the book for me. I didn't find it depressing because, despite all of his own fuckups and bad circumstances, Milo maintains his sarcastic and selfish persona throughout. He's not the only funny character, either. His big "ask" for Mediocre University is his rich friend from college, and he turns out to be just as manipulative and clever as Milo. The first few pages had me laughing so hard I had to share them with friends because I was impressed a book could make me laugh so quickly starting from scratch. The humor was also hyper-modern. An example would be when Milo goes on a short tirade about people who use terms like "interwebs and googletubes".
The hyper-modernity also shows itself in the plot. Milo and his wife struggle financially, Mediocre University is struggling financially, and the rich people who fund the University are struggling (relatively). I found this aspect of the plot brilliantly American and very close to reality. The disgruntled, over-educated creative stuck in one of a series of quotidian jobs with no opportunity for advancement. There is such authenticity in Milo's inner feeling of superiority over the world he continually fails in that I was led to believe in him myself.
I suppose the plot then, is about this conflict. Milo's (perhaps justified) inner feeling of being too clever for his job, his house, his neighborhood, and maybe even his wife, and his continual failure to even maintain what he has. But remember: it's funny.