Book II, Chapter 6
Carrie accompanies the Gormers to one of their new houses and while there meets George Dorset while taking a walk. He pleads with her to give him some proof of his wife's infidelities, implying that he wants to divorce her and marry Lily instead. Lily becomes afraid and runs away from him, telling him she cannot help. When she returns to the Gormer house, Mrs. Gormer informs her that Bertha Dorset had been there for a visit.
Lily head back to the city and finds a place in a hotel, paying more for her rent than she can afford. She is soon visited by Mr. Dorset who implores her to help him out of his situation, but Lily refuses to reveal anything. She then goes to visit Carrie Fisher and finds Rosedale in Carrie's house, most likely invited there so he and Lily could meet. After the dinner Carrie talks with Lily alone, and tells her that in order to defeat Bertha Dorset, Lily will have to either marry Mr. Dorset or marry someone else.
Lily's dual nature, her Diana-like hunt for a marriage that can save her combined with her strong sense of freedom and fear of marital commitment, will permeate her decisions and fate for the rest of the novel. She again has a choice of getting back into the society by either marrying George Dorset or going to Rosedale. Lily, however, refuses to use her letters in order to achieve this goal; she takes the moral high road and will suffer for it.
Book II, Chapter 7
Lily, having decided to try and marry Rosedale, goes on a walk with him. She tells him that she is willing to marry him now, but he informs her that the situation has changed. Rosedale admits that he does not believe the stories about her, but that marrying her would set him back several years in his attempts to break into society.
Rosedale then asks Lily why she has not revealed the letters written by Mrs. Dorset. He lays out a plan whereby Lily forces Mrs. Dorset to renew their friendship, after which she marries him and achieves the financial independence necessary to prevent Mrs. Dorset from ever attacking her again. Lily is suddenly scared by the baseness of the proposition and runs off, leaving Rosedale to think that she is really trying to protect Selden.
Rosedale explicates what the reader has already inferred: "Last year I was willing to marry you, and you wouldn't look at me; this year - well, you appear to be willing. Now, what has changed in the interval? Your situation, that's all" (265). Lily has declined to the point where she is no longer useful, and Rosedale has risen to the point where he does not need her. However, her beauty still attracts him, and his one concession is to accept her as a wife provided she reestablish her ties with Mrs. Dorset. We again see Lily recoil from the prospect of marriage at the last minute, running off and avoiding it.
Book II, Chapter 8
Lily continues slipping lower and lower along the social ladder. On one of her visits to Gerty Farish she learns that Ned Silverton has gone deeply into debt with his gambling, thereby ruining the family. His two sisters had just gone to see Gerty and ask her to find them jobs with which to help pay his debts. Lily laments to Gerty the fact that she will soon be in the same plight as the Silverton sisters if she does not find something to soon. She goes to Carrie Fisher, on whom she is relying to find her something.
Gerty meets with Selden and urges him to go to Lily and make sure that she is okay. He takes her advice and goes to visit Lily, but it turns out that Lily has already transferred to another hotel. The clerk gives him her forwarding address, and when he sees that it has a different name on it, Selden rips up the note in a rage and stalks out.
Selden's isolated world is revealed more and more, justifying what Lily said about his standards of exclusion in the first part of the book. "It was much simpler for him to judge Miss Bart by her habitual conduct than by the rare deviations from it which had thrown her so disturbingly in his way; and every act of hers which made the recurrence of such deviations more unlikely confirmed the sense of relief with which he returned to the conventional view of her" (281). This is an example of how Selden builds his own world and then exclude others based on minor reasons, in this case the rumors asserted by society. He alone of the characters will fail at an emotional level to come to terms with what he really knows about Lily Bart.
Lily now makes the transition to a hotel, again representing a sign of the lack of permanence of her abodes. The hotel is even more transitory than a ship since it can be left so much more easily. Lily's choice of accommodation is important from here onwards because it reflects the state of her life. Her final moments take place in a boarding house, a place that is as dingy and polluted as she can imagine.
Book II, Chapter 9
Lily's new job is to help a lady named Mrs. Norma Hatch into the next social tier. Lily feels as if she has entered a social level lower than that of the Gormers, but is surprised to see that Ned Silverton and Freddy Van Osburgh are members of the elite class that spend time with her new group. Lily struggles to get Mrs. Hatch to start conforming to her perception of what behavior is necessary to move upwards, and soon realizes that Ned Silverton is trying to get Freddie Van Osburgh to consider marrying Mrs. Hatch.
One afternoon Selden arrives in order to see Lily. They are polite to each other, and Selden offers himself to her someone to talk to. Lily realizes that he is frightened by the prospect of emotional feelings for her, and is upset that he is so desperate to prevent any feelings from emerging. He tells her point-blank that she needs to leave Mrs. Hatch and rejoin Gerty. Lily informs him that she cannot do that since she owes every penny of her forthcoming inheritance. She then rejects Selden as a friend and makes him leave, putting up an unemotional barrier to his presence.
The nature of the training that the characters receive is part of what destroys them. In the tense scene between Lily and Selden, "the situation between them was one which could have been cleared up only by a sudden explosion of feeling, and their whole training and habit of mind were against the chances of such an explosion" (287). Neither of them can overcome this training, a form of behavior that prevents the release of any form of emotion. While the bad side of such training is presented in this scene, recall that Lily relied on the same training to stop Mr. Trenor in his desire for her earlier.
Book II, Chapter 10
Lily realizes too late that she has to leave Mrs. Hatch in order to save her own reputation. She returns to Gerty, but is blamed by the elite society with having contrived to set up Mrs. Hatch with Freddy Van Osburgh. Gerty and Carrie Fisher conspire to find her a job in a hat shop and Lily is put to work making hats. However, her skills are no use there, and even two months later she is still being rebuked for her shoddy work. After a second rebuke for the same mistake, Lily pretends that she is sick and heads home.
She stops at a pharmacy and picks up some pills. The clerk tells her to be careful and not take to much, since an overdose of the drug has apparently already killed several people. She resumes her walk home and runs into Rosedale, who is shocked to see her. He invites her to tea, and during their conversation she reveals the entire story of her borrowing the money from Mr. Trenor and how she has to pay it back. Rosedale is shocked to learn the truth and accompanies her home, even more shocked when he sees the poor place where she lives.
Lily is starting to get lonely in her isolation. She has begun taking the drug that she purchased, a drug that is meant to combat sleeplessness but that also allows her to forget her obligations for a while. Concerned over her state, she starts to contemplate implementing the plan that Rosedale offered her before, in which she uses her letters to force Mrs. Dorset to befriend her again.
The chloral drug that Lily purchases is a sleeping agent, a means whereby she can put away the troubles of the material world. The danger here is one of death. Lily's desire to escape material problems will cause her to play with death, the only real solution for a woman of her class who has been excluded from material wealth.