As the novel opens, Esther has everything a young woman could want: a dreamy boyfriend; a string of sparkling academic successes; and a cushy job as an intern in a women's magazine, where she gets showered with free stuff and parties. While all of this makes Esther look good on paper, she's terribly unhappy. She doesn't feel personally fulfilled by what she does, and she feels as if no matter what she does or how brightly she shines, society is grooming her to become a docile housewife.
Back home, Esther feels her worst fears about herself have been confirmed. The rejection from the writing program kills her self-esteem, and she's stuck at home with her mom in the soul-crushing boredom of the suburbs for the rest of the summer.
As the summer wears on, Esther's behavior grows more erratic as her despair deepens. A visit to a psychiatrist and electroshock therapy only accelerate her decline. After a few hesitant attempts at suicide, Esther decides to end it all by crawling into a hollow underneath her house and swallowing a bottle of sleeping pills. She's discovered a few days later, barely alive.
It's touch-and-go for Esther for the first few weeks after her suicide attempt. The first two psychiatric wards do nothing to help her condition. Finally, Philomena Guinea, the woman who funds Esther's college scholarship, swoops in and deposits Esther at a private institution, where Esther finally begins to emerge from her depression.
Esther's condition improves to the point where she's allowed "town privileges," that is, she's permitted to leave the institution and go into town. Esther takes this opportunity to assert her sexual freedom and loses her virginity to a Harvard professor she meets in Cambridge. She bleeds profusely, and has to seek the help of her friend and fellow psychiatric patient Joan. Esther's wounds heal, and she doesn't experience any emotional trauma after the event, but her friend Joan commits suicide a few days after.
The novel ends with Esther entering her exit interview. While the novel doesn't tell us what happens afterward, we can assume from stray comments in the novel that Esther is indeed released from the institution.