Here's one of my highlighted quotes from about halfway into the book:

It's of some interest that the lively arts of the millennial U.S.A. treat anhedonia and internal emptiness as hip and cool. It's maybe the vestiges of the Romantic glorification of Weltschmerz, which means world-weariness or hip ennui. Maybe it's the fact that most of the arts here are produced by world-weary and sophisticated older people and then consumed by younger people who not only consume art but study it for clues on how to be cool, hip — and keep in mind that, for kids and younger people, to be hip and cool is the same as to be admired and accepted and included and so Unalone. Forget so-called peer-pressure. It's more like peer-hunger. No? We enter a spiritual puberty where we snap to the fact that the great transcendent horror is loneliness, excluded encagement in the self. Once we've hit this age, we will now give or take anything, wear any mask, to fit, be part-of, not be Alone, we young. The U.S. arts are our guide to inclusion. A how-to. We are shown how to fashion masks of ennui and jaded irony at a young age where the face is fictile enough to assume the shape of whatever it wears. And then it's stuck there, the weary cynicism that saves us from gooey sentiment and unsophisticated naïveté.

And another from near the end:

It now lately sometimes seemed like a kind of black miracle to me that people could actually care deeply about a subject or pursuit, and could go on caring this way for years on end. Could dedicate their entire lives to it. It seemed admirable and at the same time pathetic. We are all dying to give our lives away to something, maybe.

Keep reading, iammyownrushmore. I know for me, it took a couple times to really get to know the book. But now I've reread it a couple times, and the innumerable characters, the disjointed storylines, his colloquially prosaic writing style, it all comes together.