Esther, a brilliant student, attends an elite Massachusetts women's college. In a nationwide contest in 1953, she is chosen to be one of 12 guest editors for a New York City fashion magazine. This is a great honor, but Esther finds herself increasingly depressed and delusional, and she is unable either to work or enjoy herself during the June internship in Manhattan. She returns home to find that she has been denied entry to a writing class—a serious blow to what little self-esteem she has left. Gradually Esther sinks into a suicidal state, making two halfhearted suicide attempts before she overdoses and nearly dies. Esther is sent to a psychiatric facility, where she makes slow progress. As the book ends, she is on her way to a discharge interview at the hospital.
Buddy is an annoyingly self-satisfied young man from Esther's hometown. In many ways, he is her counterpart: a talented student with excellent grades, good looks, and what appears to be a sure path to a successful future. However, Buddy's relationship with his mother is oddly closer than Esther's relationship with her mother, and his patronizing view of women infuriates Esther. He is certain that if Esther knows what is good for her, she will sign on as Mrs. Buddy Willard. At one time, Esther might have wanted the same thing, but when she finds out that Buddy once had an affair, she instantly loses all respect for him. Buddy contracts tuberculosis and is sent to a sanitarium for medical students. This experience makes him somewhat less smug, but Esther is unmoved by the change.
Esther's mother is a passive-aggressive and unintuitive woman who seems no match for her brilliant, unhappy daughter. When her husband, Esther's father, dies, she never cries or allows the children to grieve. Esther is almost 20 years old before she even sees her father's grave site. Mrs. Greenwood is insensitive about Esther's rejection from a writing class, callously blurting out the news the minute Esther gets home. When Esther's health reaches a crisis point, Mrs. Greenwood seems to take the news personally, as if Esther has broken down out of spite. Even as Esther begins to recover, her relationship with her mother stays fixed; just before Esther is discharged from the hospital, her mother suggests that they pretend the previous months have just been a bad dream. She also suggests that Esther's depressive behavior is a choice. Mrs. Greenwood has not had an easy life, and Esther does not sympathize with her mother. Still, the reader comes away with the sense that Mrs. Greenwood's coldness contributes to Esther's misery.
Joan comes from Esther's hometown, and the two girls attend the same high school. Joan is a horsey, athletic girl, and she and Esther have little in common. They are barely aware of each other during college, though each knows that Buddy Willard has dated the other. When Esther vanishes after overdosing, Joan slashes her wrists and ultimately ends up at the same private hospital as Esther. Joan, a lesbian, develops a crush on Esther that is not reciprocated. Esther despises Joan even as she is fascinated by her.
Doreen is the guest editor whom Esther most admires. She is witty, cynical, and somewhat disdainful of the other interns. She attends a society college and has a sexual confidence that Esther appreciates. The two young women have a partners-in-crime friendship and often dodge their responsibilities at the magazine.
Jay Cee is the fiction editor at the fashion magazine where Esther interns. She is unglamorous and brutally decisive, and she makes it clear that she does not think much of Esther's professional prospects. Jay Cee knows "all the quality writers in the business" and speaks several languages.
Dr. Nolan becomes Esther's primary psychiatrist. She acknowledges Esther's ambitions and conflicts with social expectations, and she respects Esther. She becomes a mother figure for Esther and helps Esther understand the role her mother plays in her struggles.