Lily spends the autumn with Mrs. Peniston, enjoying the money she has earned from Trenor's investments. She gives money to Gerty's favorite charity, although she exhibits pride in her action.
Upon returning from Thanksgiving vacation in the Adirondack Mountains, Lily is visited by Rosedale. He invites her to the opera, telling her that Trenor intends to attend as well. He implies that Trenor may have less-than-honorable intentions for Lily and that he may have committed earlier infidelities. Rosedale asks Lily how her investments are doing. She is shocked that Trenor has spoken about their arrangement, but also believes that Rosedale might be able to help her financially, as well. She accepts Rosedale's invitation to the opera.
At the opera, Lily appears beautiful in new clothes. Trenor, somewhat intoxicated, accuses Lily of no longer seeking his company because she no longer requires his financial help. He insists that he would like to see her alone, and Lily agrees to meet him in Central Park the following afternoon.
Dorset enters the opera box and passes on Bertha's invitation to Lily to visit their house the following Sunday. Lily believes Bertha's letters to Selden give Lily the upper hand over Bertha.
Lily mistakes the feeling of self-importance she gets when she gives money to Gerty for altruism. This feeling is contrasted with the way she feels at the end of the chapter when she considers her possession of Bertha's letters to Selden a fitting revenge for Bertha's participation in the successful pairing of Gryce and Evie.
Lily's naiveté shows in her handling of Rosedale and Trenor. Rosedale implies that Trenor is a philanderer, an inference lost on Lily. Rather than risk a scene with the intoxicated Trenor, Lily agrees to meet him — although he's indicated he is not interested in "talking."