Lily awakens to receive letters from Mrs. Trenor and Selden, both requesting a meeting with her. Although she is worried about Selden's desire to marry her, she agrees to meet with him at four the following afternoon.

In the meantime, Lily goes to the New York home of Mrs. Trenor, where she is met by Gus Trenor. He tells her that Mrs. Trenor is sick and cannot meet with Lily, and so Lily replies that she must then leave. Trenor becomes angry that she wants to leave and tells her that she may not, because he wants to speak with her. Trenor confesses that his wife is not even home; she asked him to cancel her appointments, but he did not so that Lily would come over and she could "hear [him] out."

He first explains that Simon Rosedale has been spreading rumors about an affair between Lily and Selden ever since he saw her leaving the Benedick at the end of Chapter One. Trenor has come to believe that Lily and Selden are together, which infuriates him because he thought Lily had a romantic interest in him. He tells her that she has led him on unfairly. After ranting, Trenor suddenly orders Lily to leave after the issue of her investments is raised. As she departs, Lily realizes that she is terrified of her own loneliness, which is evident to her now because she has "no heart to lean on" in this time of distress. She decides to seek comfort from Gerty Farish.

Gerty, meanwhile, is becoming more infatuated with her cousin Selden. She thinks her fondness may be reciprocated, but she also suspects that Selden loves Lily. Nevertheless, as Lily becomes more involved in helping Gerty with her philanthropy work and learns what it means to truly live in poverty, Gerty finds herself liking Lily more.

Chapter 14 also delves into Selden's personal family history. His parents were not particularly wealthy, nor did they place a large priority on the acquisition of wealth. Selden thus grew up learning how to make do with little money, and he has always retained a detachment from those who obsess over money, including Lily. Nevertheless, Selden recognizes his increasing love for her.

On a trip into town, Selden encounters Trenor alone at a club. Trenor asks Selden to stay with him, and when Selden refuses, Trenor once again becomes angry and irritable. Later, Selden joins Gerty Farish for dinner, where they discuss Lily and her appearance during the tableaux vivants. After dinner, they discuss their thoughts on love and marriage. Selden states that even though Lily has had numerous opportunities to get married, she has always shrunk from them at the crucial moment. He leaves telling Gerty to "be good to her... you help her by believing the best of her." Gerty is jealous of Selden's obsession with Lily.