Last Updated September 5, 2023.
The titular "Rich Boy" of the story, Anson is a symbol of the worst of the rich. His life void of any real meaning, we see Anson cause immense harm to those around him—though he refuses to take any responsibility for his actions. Drinking irresponsibly and constantly chasing superficial relationships, it is clear that Anson wants to be desired by another but is completely unlikable and unable to maintain a real relationship. Upon realizing how alone he his, Anson make a small shift and begins to take more seriously his role as a leader in society, teaching a Sunday school class, sponsoring young men in the social clubs he belongs to, and giving advice to many of his friends and connections. However, it is clear that these changes are superficial: Anson's life is still fundamentally lacking meaning, and Anson's response—per usual—is to chase the pleasures of the moment and absolve himself of all personal responsibility for his actions and his unfulfilling life.
Paula is Anson's first significant love interest. They meet while Anson is at a naval training base in Florida during is short stint in the Navy, and it is clear from the beginning that their connection is less about true love for each other and more about coming from similar class positions. After Anson drunkenly mistreats Paula and fails to show up for a date, Paula rejects him. This is absolutely shocking to Anson, who always assumed that Paula would wait for him no matter what. Anson struggles to move past Paula's rejection, making it even more difficult for him to pursue other relationships with women. Eventually, Paula marries another man. She and Anson meet by chance later in life, and she admits to him that she never truly loved him, which disturbs him. Paula dies in childbirth, and though Anson appears to be affected by this news, it does not bring about a change in his personality or his approach to women. Throughout the story, Anson displays a complete lack of care for Paula, yet he is simultaneously unable to get over her.
Following his breakup with Paula, Dolly becomes Anson's love interest for a time. Their relationship embodies the emptiness and pettiness that Fitzgerald sees in the rich and consists of little more than them working to make each other jealous. Anson eventually cruelly rejects Dolly, revealing that he had simply been playing with her and was still thoroughly fixated on Paula.