The story opens in Lake Forest, Illinois, with a family observing their dying mother. She has been sick with cancer for a long time, and refuses to return to the hospital, which could prove fatal considering how thin her blood is. Any bleeding could cause her to die. Soin, she gets a nosebleed that won't stop, prompting the family to panic.
Soon, they establish that their father recently died as well, also from cancer. Their remaining family consists of Eggers, the eldest (21), Beth, the middle child, and Toph (7). Given these facts, the family soon pressures the mother into going to the hospital, where they wait as she is examined. Eggers flashes back once again to his father's death and funeral, which he left early to have sex with his girlfriend. The family sits in silence in the hospital.
Their mother is eventually well enough to leave the hospital, but even at home she is still not well. She is dying still, and every day she degenerates further. Within a few weeks, she dies and the family packs up and moves out west to Berkeley, California. Beth attends law school there and the rest of the family is set to lease a house with a good view.
Beth soon becomes preoccupied by law school, leaving Eggers and Toph to bond. They spend the summer together doing brotherly things like playing music and going to the beach. The two of them are living on not a lot of money, mostly government assistance, but they try to make the most out of their days in the sun. After the summer ends, they struggle to find housing since they are not the ideal tenants. Eventually, they find a run-down building in Berkeley that they are able to rent and settle there.
As school starts up again, Toph and Eggers are still very close. They live like young bachelors, messily and without abandon. Toph also starts school, but it is awkward at an open house when Toph does not have a parent. Eggers fills in for one, but the situation is uncomfortable. He cannot bond with the other parents and he is ignored by most people, leaving him feeling very isolated and pathless.
Searching for this path, he heads to San Francisco. He and his friend Moodie begin a magazine called Might, a youth-centric magazine for people their own age. At the same time, MTV begins shooting The Real World in San Francisco, and Eggers is invited back for a second round interview. He does not do well in this due to his background, as the show has already cast a white middle-class man with a sad life. He is disheartened, but throws himself into his work.
The magazine gains publicity, but still fails to make money. Eggers struggles to make ends meet, and moves Toph out to the city with him. He is increasingly unhappy, which comes to a head when his friend John overdoses on pills in a clear suicide attempt. He spends time with him in the hospital, thinking about his own parents. This memory is compounded when he has to pass a kidney stone, which leaves him in great pain. Another one of his friends, who drove him to the hospital, suffers a massive fall and goes into a coma. The long-term damage is irreparable.
This forces him to confront his feelings about his parents and he wishes he had their ashes. Eggers returns to Illinois and finds the funeral home where he cremated them. He picks up their ashes and then returns to California, where he ends the magazine and collects Toph. The two of them move to New York, and the novel ends.