The chapter begins in Gerty's apartment where Gerty has spent the night dreaming after realizing that she has fallen in love with Selden.
The narrator explains Selden's upbringing. His parents' lack of wealth was balanced by their happiness with each other. Consequently, Selden has learned to appreciate a simple lifestyle and to disdain the accumulation of material possessions as "aimless profusion."
After his encounter with Lily the previous evening, Selden is certain that he is in love with her and that she wishes him to propose. Selden returns from Albany to New York City, where he goes to his club. There, Trenor entreats Selden to eat supper with him, which. Selden refuses. He receives Lily's note regarding the following day's meeting and is invigorated, assuming that Lily will accept his proposal.
Selden visits Gerty for dinner. The two discuss Lily until Gerty surmises that Selden is in love with Lily. Although heartbroken, Gerty does not reveal her feelings. She tells Seldon that Lily was to dine at Carry's home, and Selden excuses himself to see Lily there.
When he arrives at Carry's house, Selden is told that Lily has already left. A guest says that he heard Lily tell the hansom driver to take her to the Trenor residence, even though it is well known that Judy is away and Trenor is alone at their town house.
Selden leaves Carry's party and is joined by Ned Van Alstyne in his walk down the street. As they near the Trenor residence, the pair observes Lily leaving the house and Trenor standing in the open doorway. Van Alstyne swears Selden to secrecy, explaining that "appearances are deceptive."
Gerty blames Lily for stealing Selden's affections from her, and for possibly the first time in her life, she allows herself to feel hate.
Following her confrontation with Trenor, Lily arrives unannounced at Gerty's apartment. Although Gerty's first inclination is revulsion toward Lily, she receives her tenderly when she realizes that Lily is terribly upset. Lily is hysterical, proclaiming herself to be bad. Gerty tries to reconstruct Lily's evening to discover what is troubling her. She recounts that she knows Lily had dinner at Carry's home and that Selden went there to find her. The mention of Selden's name prompts Lily to ask Gerty if she thinks her cousin can ever again think highly enough of Lily to help her. Gerty struggles with the question but responds that she is certain Selden will help Lily.
More than any other chapter in The House of Mirth, Chapter XIV reveals that the novel was written in a serial format. This style is evidenced by the nonlinear presentation of the chapter, in which Wharton backs up time in order to fill the reader in on the thoughts and feelings of Gerty and Selden as they evolve after the Brys' dinner party. The reader can then understand what is happening to Selden and Gerty prior to and during Lily's fateful visit with Trenor.
Gerty previously had enjoyed life and romance only secondhand. Her newfound love for Selden and her charitable disposition prompt her to share her good fortune with others. Gerty believes that her love for Selden is reciprocal because of his frequent visits, and that the two have attained a higher degree of sympathy through their mutual affection for Lily.
Gerty's drawing Lily into her charitable work at the Girls Club, and Lily's participation, serves as a foreshadowing of Lily's future economic plight. The narrator regards Lily as learning to view the economically disadvantaged as individuals rather than en masse.
The narrator uses Van Alstyne to point out the values of old-money New York socialites in two passages. In the first, he sums up the social values of the day regarding unmarried attractive women: "When a girl's as good-looking as that [Lily] she'd better marry; then no questions are asked. In our imperfectly organized society there is no provision as yet for the young woman who claims privileges of marriage without assuming its obligations." The second instance occurs when Van Alstyne accompanies Selden after leaving Carry's house. He points out the differences of architecture between old money, like the Trenors' home, and new money, like the Brys' estate. He disparages the ostentatious nature of the Brys' home and compliments the Trenors' more austere Corinthian style.