The Great Gatsby and The Beautiful and Damned are both known for their razor-sharp critiques of society and societal expectation—especially for the upper classes—during the Jazz Age in the United States. Key female characters in both books experience conflict between the financial and social stability found in the institution of marriage and their own desires. In The Great Gatsby, Daisy never seriously considers leaving her husband for Gatsby, despite her affair, because it is simply not in line with her idea of the American Dream. In The Beautiful and Damned, Gloria also follows the American Dream, retreating to the refuge and safety of marriage, only to later discover that its stability and fulfillment were specious. Through these characters, Fitzgerald casts doubt on whether the American Dream is worth seeking as it often stands in opposition to what brings people true happiness and love.
Both Dot in The Beautiful and Damned and Daisy in The Great Gatsby represent newfound freedom for women during the Jazz Age, where stricter traditions of the Victorian Age were systemically disregarded by the avant-garde. In both of these cases, their freedom was symbolized through their romantic trysts. In The Beautiful and Damned, Gloria chooses to discard her traditional duties as a housewife. The choices these three women make with their newfound freedom ultimately lead to tragedy. Through these examples, Fitzgerald draws attention to the inevitable conflicts that arise when Old World orders are replaced.