The narrator explains his theory on the very rich – “They are different from you and me.” To emphasize this difference, the narrator says he must stick to his point of view, for if he sympathizes with Anston Hunter he will “have nothing to show but a preposterous movie.”
Hunter’s father wanted his sons to “grow up into right-living and successful men.” Because of his narrow and privileged upbringing, Hunter becomes self-absorbed and egotistical. “He disdained to struggle with other boys for precedence – he expected it to be given him freely.” He was unsuccessful at Yale as he did not demonstrate the “proper awe” for the institution.
Hunter falls in love with Paula Legendre, “a conservative and rather proper girl” who is wealthy like him. He is easily distracted, however, and disgraces himself by getting drunk and spoiling an evening with Paula’s family. Their engagement is postponed as a result.
Paula sees “two alternating personalities” within Hunter. He could impress with “his strong, attractive presence” but his other side was “gross, humorous, reckless of everything but pleasure.” He still believes he can control Paula and that they will marry “one day,” despite throwing himself into the New York social scene. Hunter is also dedicated to his work on Wall Street. Paula continues to write to him and when they meet he is drawn to her. Arrogantly, he still insists that the relationship be defined solely on his terms.
She does not wait, however, and when Hunter receives the telegram announcing her engagement and imminent marriage he cries “like a child” for three days. Hunter becomes cynical, and has an affair with Dolly Karger: Dolly is “slackly and indiscreetly wild”. She is drawn to both sides of Hunter’s personality that Paula first observed – “she felt both the sybarite and the solid rock.”
The narrator can see the tragedy approaching and is glad when Dolly’s downfall “would not be consummated in my sight.” Dolly plays with Hunter, claiming she has another suitor. He is annoyed by the game and continues his courting only to assert his control over her. “If she wanted to know to whom she belonged she would see,” he broods. Hunter twice attempts to consummate his affair with Dolly, but Paula’s image haunts him and he tells Dolly that he does not love her and she must wait for one who does.
Once Dolly and Paula are both married, Hunter devotes his time to advising others. “He came to take a vicarious pleasure in happy marriages.” He discovers his Aunt Edna is having an affair and he confronts the couple, threatening to tell his uncle and the young man’s father. Cary Sloane is found dead by suicide the next day. Hunter takes no responsibility for the boy’s death, but is no longer welcome in his uncle’s house. Hunter has few friends to call on, and as he nears thirty he “felt his estrangement most keenly.”
Hunter sees Paula again. She has remarried and is pregnant. She reveals that she was never in love with Hunter. He is wounded by this knowledge, but still cannot rationalize her judgment as anything to do with his own failings. He becomes less dynamic at work, and a vacation is advised. Paula dies in childbirth. Hunter is at first saddened, and then over cocktails aboard ship he spies an attractive girl. He drinks champagne with her and then abandons his friend, the narrator, for her company.
The narrator’s statement on the “very rich” is often quoted as an illustration of the gap between the society in which many people lived – including Fitzgerald himself – and the society which they vainly aspired to. The story is said to be based on one of Fitzgerald’s friends, Ludlow Fowler. Fitzgerald professed at the time that “The Rich Boy” was “one of the best things I have ever done.”
There are parallels which can be drawn with Fitzgerald’s own experiences as well as his friend. Hunter’s lack of success at Yale reflects Fitzgerald’s own unsuccessful college experience as he, like Hunter, was diverted by to self-indulgence rather than study.
Paula Legendre is not typical of Fitzgerald’s heroines in that she is “rather proper.” She is the sort of girl Hunter ought to marry, and therefore never will. He remains attracted physically to the “wild” ladies of “high color” like Dolly and the young lady on the cruise. His material urges direct him to possess and own people in the way he does things, and this approach does not appeal to the women around him.
Despite Hunter's easy use of women and his careless, privileged attitude, it is implied that he does uphold the sexual standards of his day. Considering that he is being presented as an unsympathetic, boorish protagonist, it is surprising when he refuses to sleep with Dolly without loving her. Dolly of course receives this as very cruel treatment. But in a way, it is the first sign of Hunter's respect for Dolly that he tells her to wait for someone who loves her properly.
Hunter cannot see that his treatment of Paula leads to her marrying someone else. As she is to marry again later, it is obvious that her first marriage was not a happy one. Despite Paula telling him that she was never in love with Hunter, only controlled by him, Hunter cannot see that any responsibility lies within himself – “I could settle down if women were different…If I didn’t understand so much about them, if women didn’t spoil you for other women, if they had only a little pride.” Paula does have pride: she chooses to marry rather than wait indefinitely for Hunter, and she finds love in her second husband. When she tells Hunter “we wouldn’t have been happy,” he is injured. The metaphor used is a physical one: “The phrase struck at him from behind.” However, there is an irony in that Hunter was unlikely to think in terms of “we.” His motivations are purely selfish.
The narrator is able to see Hunter’s failings as he is not “like” him. When they are mourning Paula’s death on the cruise, Hunter is distracted again by another woman. She is described physically in terms similar to Dolly. The narrator is resigned to being abandoned by his friend, observing that Hunter needs not love itself, but to be loved – “I don’t think he was ever happy unless some one was in love with him.”