The prologue takes place at the story’s end, in the year 2020 when most of the characters are in their fifties. Mallory Blessing, a teacher on Nantucket Island in Massachusetts, is dying of brain cancer in her early fifties. She asks her son, 19-year-old Link, to call a phone number written on an envelope in her desk—presumably to let someone know about her illness. The number belongs to Jake McCloud, the husband of a woman who is running for President of the United States. Link is shocked, not realizing that Jake and his mother know each other. Jake is distraught upon hearing about Mallory’s cancer and promises to visit her right away. 

The chapter moves to the earliest point of the novel’s timeline, 1993. Mallory is 24 years old and living in New York with her wealthy friend Leland Gladstone. She has a dead-end job as a receptionist while Leland has snatched up a desirable job at a literary magazine that both Mallory and Leland applied for. Tension between the two friends is running high, with Leland disdaining Mallory’s demeanor and lifestyle and Mallory resenting Leland’s success.