A few weeks later, Lily separates from Norma Hatch, after sensing that she was being used to facilitate an unacceptable social transaction. Later, she learns that Stancy’s goal was to marry Freddy Van Osburgh to Norma Hatch, which members of the upper class were able to prevent by sending the young boy to Europe. Although Lily left Mrs. Hatch before this plan became obvious, Lily’s name remained involved in the scandal and served to further tarnish her reputation.
The unfairness of being once again involved in a scandal in which Lily has no say reinforces the idea that she is destined to an unjust, tragic fate. The details of this planned marriage also highlight, once again, the lack of trustworthy relationships in this milieu, since even a lifelong, supposedly emotional commitment such as marriage becomes part of other people’s manipulative schemes.
Now, thanks to the combined efforts of Gerty Farish and Carry Fisher, Lily is working for Mme. Regina, a hat-maker. Although Lily hopes to open her own shop one day, she soon realizes that, despite working there for over two months, she is still clumsy and cannot sew as well as the other girls, who have been trained in this trade for many years.
Once again, Lily’s freedom appears restricted by her upbringing and her education, which have destined her to a plush life of high-society socialization instead of investing in her talents in a more productive way, for example by cultivating her intellect and skills.
The other girls, who know Lily’s story, do not treat her any differently, but do consider her background the main explanation for Lily’s incompetence. In the meantime, Lily listens to the girls gossip about the people who will buy their hats and realizes that the workers discuss the details of high society, occasionally mentioning a name that Lily recognizes as one of her friends.
For the first time in her life, Lily is forced to realize that the social prestige she has taken so much pride in is not necessarily valued by the rest of society, which tends to place more emphasis on a person’s concrete skills. This highlights Lily’s double isolation, as she is excluded from high society and looked down upon by members of the working class.
One day, Lily’s supervisor, Miss Haines, scolds for failing to sew carefully enough. After work, Lily feels depressed to be part of the working class but receives some kind words from a fellow worker, Miss Kilroy, who tries to encourage her by telling Lily to go lie down, since Lily had said that she was feeling unwell. Having refused Gerty’s hospitality, Lily walks home to her boarding-house.
Miss Kilroy’s kindness emphasizes that no social class produces a single type of personality but, rather, that a person’s worth depends on their behavior, not their class. This serves as the first signal to Lily that being part of the working class is not shameful in itself, since her identity and worth depends on nothing more than her own self—not her material environment.
On her way home, Lily stops by the chemist’s, where she receives her sleeping drugs, although the chemist looks at her in an intense way and tells her that only a few drops above the recommended dose could be fatal. Lily, who had feared that the chemist might refuse to give her the drug, simply feels relieved to have it in her possession.
Lily’s desperate need for potent sleeping medication reveals that she is mentally unwell, unable to come to terms with her current life and to confront the moral dilemma that would determine whether she can re-enter high society. The chemist’s warning serves as a foreboding signal of Lily’s tragic fate.
As Lily exits the store, she suddenly runs into Rosedale, who is shocked to see how unwell Lily looks. He takes her to a hotel for a cup of tea, which Lily enjoys because it is her only strategy to keep from falling asleep during the day, at the same time as her sleeping drug is her only method for falling asleep at night.
Lily’s encounter with Rosedale serves as a reminder of her moral dilemma: in choosing to blackmail Bertha, she could put all of her financial and mental troubles aside. Rosedale’s presence thus highlights the fact that Lily is going to have to choose between two worlds: her current, morally upright but miserable situation, or a degraded, yet materially comfortable one.
As Rosedale observes Lily, he is once again startled by her beauty. He asks about her life, although he is embarrassed to remember the rumors concerning Mrs. Hatch, and is shocked to learn that Lily is now part of the working class. Lily explains that she left Mrs. Hatch so that people would not think she was involved in helping Mrs. Hatch marry Freddy Van Osburgh, but that she now realizes even such prudence was useless, since rumors spread about her anyway. Rosedale, though, insists that he knew Lily would never be involved in such an affair, which makes Lily feel reassured.
Lily’s desire to explain herself with regards to the Norma Hatch scandal suggests that it is difficult for her to retain moral high ground while being ostracized by the rest of society. Rosedale’s trust in Lily confirms how hypocritical high society is, since rumors will keep circulating about Lily even though the people who know her are convinced that she is innocent—yet find themselves unwilling or unable to protect her from harm.
When Rosedale inquires further about Lily’s situation, she finds herself admitting to him that she owes her aunt’s entire legacy. For the first time, she tells the entire truth about her business with Gus Trenor and thinks it might make her feel relieved, but it also increases her sense of misery. However, Rosedale finds this story encouraging, since it clears Lily of blame. He insists on accompanying her home and is shocked at discovering the boarding-house where Lily lives, but Lily simply says she is tired of depending on her friends. Finally, she accepts his offer to come visit her again, realizing that this prospect actually makes her happy.
Lily’s desire to be understood reveals that she still trusts in justice, despite her cynical attitude toward high society. Lily’s willingness to live in poverty in order to protect her moral compass—instead of other people’s opinions, which are based on slanderous rumors—demonstrates strong values that set her apart from the rest of high society. Her appreciation for Rosedale, highlights his surprising loyalty and kindness, instead of Lily’s self-interested ambitions.
That evening, in her room, Lily feels lonely. Carry Fisher has been afraid for people to think that she was involved in the scandal with Mrs. Hatch, and has therefore taken a break from helping Lily—which Lily understands and excuses. Although Gerty remains her only loyal friend, Lily avoids her because she fears running into Selden, which she feels would only bring her pain.
Lily’s justification of Carry’s behavior reveals how tolerant she is to society’s norms, even when they are visibly unfair. Lily’s avoidance of Selden is reminiscent of Selden’s own detachment from Lily, and suggests that the two characters are not kept apart because of insufficient feelings, but because of the different social worlds they want to belong to.
Reflecting on the necessity to repay Gus Trenor’s debt, Lily wonders if she could use her aunt’s legacy to open her own hat-making business and, over the course of years, give Trenor his money back. However, she also worries that she might lose her sense of moral obligation and eventually accept being forever in Trenor’s debt. She knows that her contempt for poverty might lead her to renounce to her ideals and, perhaps, even encourage her to follow Rosedale’s original plan to re-enter high society. Finally, she realizes that her only hope lies in her sleeping drugs.
Lily’s desire to repay Gus, as well as her honesty about her moral doubts, reveal how seriously she reflects about moral issues and her own flaws. She values her moral dignity in the same way she admires her own beauty, and does not want to allow herself to behave in a dishonorable way. Lily’s mention of her sleeping drugs serves as a dark presage of her tragic death, since, if she cannot find a way to solve her problems, she would at least be happy to escape them.