Spending the autumn at home rather than the Bellomont, Lily begins to save up her finances. She also takes interest in philanthropy after being introduced to charitable giving by Gerty Farish, something which will factor in more later in the novel. Meanwhile, Carry Fisher invites her on an outing to the Adirondack Mountains over Thanksgiving, to which Lily readily assents, enjoying the trip very much.
Upon returning, Lily receives a visit from Simon Rosedale, who invites her to the opera. He tells her that he knows of her investment successes, which angers Lily because she now knows that Gus Trenor has been telling people about her speculation. She goes to the opera in order to show off her beautiful looks, and she decides to forgive Trenor for telling people about her financial success. Nevertheless, Trenor confronts Lily and tells her that she does not spend enough time with him anymore; he thinks she is using him only to handle her finances. Trenor is very angry and blunt as he criticizes Lily, which scares her to some extent because she now knows that Trenor feels that she owes him something. Later on at the opera, Lily speaks with George Dorset, which reminds Lily that she still has the letters that Bertha Dorset wrote to Selden. Instead of using the letters against Bertha, Lily decides that she will forgive Bertha even though she ruined Lily's chances of marrying Gryce.
As the holiday season begins in New York, we learn that the autumn made for bad trading on Wall Street, leaving thousands of people poor. However, Rosedale has almost doubled his money after investing in the right stocks. He is beginning to look upon Lily as a potential bride.
Meanwhile, Lily is having troubles with her cousin, Grace Stepney. Both women are vying for the affection of Mrs. Peniston, and the resourceful Lily manages to deny Grace an invitation to one of Mrs. Peniston's big dinner parties. In turn, Grace tells Mrs. Peniston that Lily and Gus Trenor may be having an affair because they have been seen walking alone together in the park. Grace suspects that Lily has financial reasons for flirting with Trenor, and Grace further tells Mrs. Peniston that Lily plays cards for money and has accrued a gambling debt, news which infuriates Mrs. Peniston and makes her angry with Lily.
We see that Lily enjoys spending time with George Dorset, but she does not like being around Trenor, who is in an "unimaginable mood." Trenor married young and has had difficulty relating to women, making him unpredictable. He also lost a lot of money in the stock market over the preceding several months. Nevertheless, Lily decides to return to the Bellomont after the New Year, and she finds the house inhabited by a different brand of people, who do not play bridge and share little in common with one another. Lily tries to be a unifying force, but meets with resistance because the others seem unwilling to accept her leadership.
To establish the Bry family in the society, Mrs. Bry decides to put on a large fashion show, to be organized by Carry Fisher, in the Brys' conservatory. Lily is one of many people to participate in this "tableaux vivante"—an art form in which people wear costumes and pose in imitation of famous artistic works. (Tableaux vivants were sometimes part of social gatherings and can be thought of as art-inspired masquerade parties.) To prepare for the party Lily adorns herself in her finest dress. Her visage is described by attendees as both realistic and beautiful. At the show, Lily and Selden retreat to the garden briefly, where they sit and talk on a bench. Selden moves in and kisses Lily lightly, but Lily stresses that she cannot marry him for financial reasons. They return to the house together, where Trenor finds Lily and once again expresses his bitter feelings toward her for not spending more time with him.
We see once again, at the beginning of Chapter Ten, that money gives Lily a sense of freedom from her other obligations, but unfortunately, Lily can never hold on to money for very long. One of the motifs of this novel is the meaning of financial wealth. Money is in fact a symbol in the novel, but it stands for different things to different people. To Lily, money represents freedom from her tedious obligations and the ability to live life however she wants. To Selden, who grew up in a humble family, money is not as important as the enjoyment of life and happiness in relationships. Selden, who always plays the outside observer to the social world, has seen that money is coveted and can lead people to some very serious problems if they deal with it carelessly in hopes of making more (particularly by gambling). It is, after all, her lust for money that leads Lily to gamble and speculate on Wall Street, both of which lead to her financial ruin and expulsion from society.
By this point in the novel, it is clear that Trenor has a romantic interest in Lily. When Lily asked him to invest for her, he hoped that Lily reciprocated that interest, but he is slowly realizing that she is not interested in him except as a tool by which she can make money. Trenor is one of the more interesting characters in the novel because of his rash anger that leads him to lose his temper. He is obviously very lonely and unhappy with his marriage to Judy Trenor, and he is trying to find companionship in his otherwise-loveless life.
The Bry fashion show presents an interesting question of reality. Lily's pose in the tableaux vivants is virtually perfect; everyone admires her as if she were a beautiful work of art to be studied. Lily in costume is wearing her finest dress and looks her best, which are signs of wealth and social prestige. However, outside of this aristocratic imaginary world, Lily does not always look beautiful, she is not flawless, and she is seldom admired by everyone in high society. The real Lily is "detached," as the narrator says, from her image in the show. The Lily of the masquerade, moreover, becomes a symbol for what Lily aspires to be.
At the same time, however, we must take into account the role of acting in the novel, which comes up continuously. Keep in mind that no one at the dinner parties lets his or her "true self" emerge. Everyone is acting to create a guise that will make others esteem them more. Thus, the Lily we see at the parties, like the Lily in the tableaux vivants, is a false representation of reality that does not accurately describe the truth. Indeed, all Lily's decisions are based on how people will perceive her, as though she were always calculating the ideal way to make herself more popular. One of the problems the novel addresses is the role of the true self; what is Lily's true personality? One of her only real gut instincts is her hatred of "dinginess" she inherited from her mother; much of her acting is solely designed to avoid that dinginess, but at the same time Lily must always live according to the rules of society. In keeping with the slavery-versus-freedom motif, Lily is a slave to acting a part that will make her liked.