Esther gets a call the next morning from Constantin, an interpreter at the United Nations. Mrs. Willard had introduced Esther to Constantin, who was now calling to arrange a meeting for her so that she could see the United Nations. Esther expects that he will be short and ugly, and she would look down on him the way she does Buddy Willard, who she believes to be a hypocrite despite her initial conviction that he was the most wonderful boy she had ever seen. Buddy wants to marry her, even though Esther now hates him. Esther reads from her new book a story of a Jewish man and a Catholic nun who meet regularly at a fig tree then part after an awful event, and Esther compares herself and Buddy to these two characters. Buddy has a very scientific mind; he compares a poem to "a piece of dust." She reminisces about how Buddy Willard told her how he was going to the sophomore prom at Esther's college with Joan Giling, presumably because she asked months ago. Although this makes Esther jealous, she goes to the Yale junior prom with him. He treats her like a friend or a cousin during most of the dance, but at the end they go up to the chemistry lab, where he kisses her.
Buddy Willard, although he appears minimally as a character during the present frame of the story, occupies a significant place in Esther Greenwood's life and is a frequent preoccupation for her. For Esther, Buddy Willard is a symbol of her deflated expectations, yet the specific reason why Buddy Willard has proved such a disappointment will only later be revealed. Esther's disappointment is borne of an idealistic treatment of Buddy Willard; he disappoints her so greatly precisely because she considered him "the most wonderful boy" she had ever seen and thus positions him so that he may only be degraded. Whatever his faults, whether real or exaggerated by Esther, Buddy Willard is one facet of the repression that Esther faces. In this chapter, the repression is an intellectual one; with his scientific approach to matters, Buddy Willard dismisses the more artistic and literary mind of Esther, shown most clearly when he dismisses a poem as a "piece of dust."
The details of Buddy's and Esther's courtship establish Esther Greenwood as more repressed than even her actions around Doreen would imply. She compares her courtship with Buddy to what is essentially a fairy tale, and thinks of her relationship with him only in terms of a single kiss. This repression additionally relates to the sense of confinement that Esther feels, but in this case it is specifically self-inflicted; one of the obstacles that Esther must overcome is her idealized and innocent view of romantic relations in which there is no room between the spectrum of the innocent Betsy and the worldly Doreen.
Esther reminisces about how she kept begging Buddy to show her some really interesting hospital sights, so one Friday she cut classes and visited him for a long weekend. Buddy showed her a hall where they kept big glass bottles full of babies that had died before they were born. Buddy shows her the birth of a baby, which horrifies Esther. When she hears about the drug that the women will take to make her forget the pain, she thinks that it sounds like a sort of drug that a man would invent. Afterward, Esther nearly asks Buddy if there are any other ways to have babies; for some reason she thinks it is important to stay awake to make sure later that the baby is actually yours. Later, Buddy asks her if she has ever seen a man, and she says only statues. He then asks if she would like to see him. Buddy undresses, telling her that she ought to get used to seeing him like this, then asks to see how she looks naked. She undresses for him. After they dress, she asks Buddy if he has ever had an affair. Buddy tells her that he has gone to bed with a woman. Buddy tells how he was seduced by a waitress at the hotel where he worked as a busboy. Esther is offended not that Buddy slept with someone else, but that he pretends that Esther is so sexy and he is so pure, when all the time he had been having an affair with a "tarty" waitress. Buddy tells Esther that when his mother asked about Gladys, the waitress, Buddy replied that Gladys was "free, white and twenty-one." Esther knows that Buddy would never talk to his mother as rudely as that for her. Later, Esther gets a call from Buddy in Boston. He had caught TB and was going to the Adirondacks on a scholarship for medical students who caught TB. Buddy has always been proud of his perfect health and thinks that all of Esther's illnesses are psychosomatic. Esther thinks that the TB might be punishment for Buddy living the double life he lived and feeling so superior to others.
Sylvia Plath focuses on Esther's view on sexuality in this chapter, in which she approaches the subject from two very divergent perspectives. The first perspective is a clinical and medical view of sexuality, as shown by Esther's visit with Buddy to the hospital ward and the details of that visit. The second is a more idealistic and moral sense of sexuality, as demonstrated by her reaction to Buddy's disclosure that he had an affair with the waitress. Plath uses intense medical imagery, often grotesque, to portray this first perspective on sexuality; she perceives this in terms of procreation that ends in either painful, agonizing childbirth or in the macabre stillbirths that she sees in bottles at the hospital. This also confirms Esther's view on sexuality as related to violence and pain, earlier established during the incident with Doreen and Lenny Shepherd.
Part of this perspective on sexuality comes from Buddy Willard himself, who teaches' Esther about the male form by disrobing as one would do for a doctor and not an intended lover. As Plath describes Buddy, he seems more and more responsible for Esther's dissatisfaction with the world. He treats her as childish and foolish. His teaching Esther about the male body is both offensive and presumptuous; he places himself as a living anatomy text because he believes that Esther will certainly be his wife someday.
However, despite Buddy Willard's obvious problems with Esther, the greatest problem that Esther has with Buddy is self-inflicted. She can view Buddy only as an idealized hero or a person who commits tawdry and sordid actions. She cannot reconcile the two facets of Buddy, and instead views him as a person leading a double life' instead of considering that both aspects of Buddy might exist in the same person.
Esther meets Constantin, who is handsome but too short. He differs from American men most in that he has intuition. While at the United Nations, Esther realizes that it has never occurred to her that before that she had only been purely happy until she was nine years old. After that, she had never been really happy again. While watching Constantin and another interpreter, Esther realizes that she cannot cook, does not know shorthand and cannot dance. Her talent is for winning scholarships and prizes, but that era is coming to an end. Esther sees her life "branching out before [her] like the green fig tree in the story" she read earlier, and from the tip of each branch a wonderful future beckons. However, Esther sees herself sitting in the crotch of the fig tree, starving simply because she cannot decide which figs to choose.
After getting a bite to eat with Constantin, Esther decides that she will let Constantin seduce her. The only boy other than Buddy Willard whom Esther considered sleeping with was Eric, a bitter Southerner from Yale who found that his date had eloped with a taxi driver. Eric had told Esther how his first time was at a whorehouse, for he went to a Southern prep school that had an unwritten rule that its students lost their virginity before they graduated.
Esther goes to Constantin's room under the pretense that she likes balalaika music. She considers an article from Readers' Digest that her mother had given her called "In Defense of Chastity," but thinks that it holds men and women to different standards. She sees the world in terms of virgins and those who have had sex, rather than other divisions such as men and women, black and white. She thinks about what it would be like to be married to Constantin, Esther merely falls asleep beside Constantin.
In this chapter, Sylvia Plath yet again focuses on the two recurring themes of The Bell Jar, Esther Greenwood's anxiety over her future and her problems dealing with her own and others' sexuality. Sylvia Plath relates Esther's anxieties over her future to more general problems with gender roles in the early fifties society in which Esther lives; her problem is not that she believes she will be unsuccessful at whatever career she chooses. Instead, part of the problem seems to be that she cannot reconcile a successful career that she may choose with the traditional gender roles of her society. Esther worries most that she cannot cook nor take shorthand, for these are tasks traditionally performed by a wife or a female secretary; ironically, Esther worries about not being able to fulfill mundane duties rather than worrying about larger questions of what she do as a successful career woman. In essence, her problem is that she has too many options, but no satisfying option that can conform to what is traditionally expected of her.
Esther's decision to abandon her longtime devotion to chastity can be interpreted several different ways. Most directly relating to her situation with Buddy Willard, her decision to let Constantin seduce her is a reaction and revenge against Buddy Willard. More generally, the decision may represent an assertion of her independence in the face of the societal repression around her. This idea is corroborated by the mention of the "In Defense of Chastity" article and Esther's conviction that she is doing something quite improper.
However, the most likely interpretation the aligns with Esther's increasing mental illness is that Esther decides to let Constantin seduce her primarily as a move of desperation. She wishes to abandon the moral system that she believes has failed her by proving Buddy Willard to be a fraud. Also, since Esther sees the world in stark terms of contraries, she believes that the simply loss of her virginity will render her a different person and she will thus escape the confinement in which she presently finds herself. Her decision is thus not a move of empowerment, but instead a sign of great weakness and frailty.
Esther thinks about how Mr. Willard drove her up to the Adirondacks on the day after Christmas to visit Buddy at his sanatorium, where she finds that Buddy is now fat, for the doctors stuff them day after day and let then do little. Buddy gives her an ashtray, even though she does not smoke. Buddy then proposes to Esther, who has an awful impulse to laugh. Esther tells him that she will never get married. She admits that she is a neurotic, as Buddy had once told her.
Esther further reminisces about going skiing with Buddy Willard, and how she thought that she might kill herself doing so. She does get hurt, however, and has her leg broken in two places. As she lies on the snow, Esther vows that she will go up the mountain again, but Buddy tells her that she will be stuck in a cast for months.
In this chapter, Sylvia Plath lends credence to the idea that it is repression that drives Esther Greenwood to despair and depression. Plath once again implies that Esther suffers from the stifling intellectual atmosphere that Buddy has created for her, in which her ideas and emotions are diagnosed as mere neuroses instead of legitimate choices and decisions. The definition given of neuroses also relates to Esther's indecision about her possible career path; she defines being neurotic as a person who wants "two mutually exclusive things at one and the same time," implying an inability to choose a single path. Buddy Willard also comes to symbolize in this chapter the broader forces of society that repress Esther; he literally calls her "crazy" for never wanting to get married, thus assuming that the only sane choice for a woman is to become a wife, despite Esther's obvious questioning of that value system.
Sylvia Plath further foreshadows the eventual suicide attempt by Esther with the anecdote concerning Esther skiing. She considers the possibility that she may die while skiing, yet even after she breaks her leg doing so she wishes to attempt it again. Esther seems somewhat incapable of realizing the effect that physical actions have on her body; this mental disjunction between mind and body will manifest itself later during her suicide attempt.