Set in New York City in the first decade of the twentieth century, the novel begins at Grand Central Station on a Monday afternoon in early September. At the train station, Lawrence Selden is approached by a casual acquaintance, Lily Bart. Lily has two hours to spend before her train arrives, and recruits Selden to entertain her. The pair leaves the station and travels to Selden's apartment building, The Benedick.
Over tea in Selden's apartment, Lily reveals her desire to have rooms of her own. She acknowledges that Selden's cousin, Gerty Farish, lives in an apartment, but shares the opinion of most society women — that only governesses, widows, or unmarriageable women live in apartments.
The pair's conversation turns to reasons why Selden seldom visits Lily at her residence in her aunt's — Mrs. Peniston's — house. Selden acknowledges that he is not a suitable suitor for Lily, or, at any rate, that he does not visit often because he is aware that Lily is not interested in him romantically. Lily rebukes Selden for presumptuously attempting to initiate a romantic engagement with her, and reveals that she has long considered Selden a confidante. She also reveals that she knows her female peers regard her as tiresome, and are beginning to become more obvious regarding their opinion that she should marry.
The two smoke cigarettes, which Lily lights from the end of Selden's, giving him cause to admire her beauty. They discuss the merits of collecting rare and first-edition books. Lily asks Selden if he minds not having enough money to purchase the books he wishes to own. He confesses that he is not a "saint on a pillar," indicating that he wishes to have more money than he earns. The conversation turns to what a man may choose to do in contrast to what a woman is forced to do regarding marriage as an economic arrangement.
