Toomer opens the book with vivid depictions of individual women, showcasing society's varied perspectives and the intense emotions men often impose on them. The first character, Karintha, is portrayed as a tragic and mysterious figure, lacking a distinct personality and defined only by her physical beauty. As a child, she is seen as a sexual object, even by men who won't admit it. Her beauty allows her to act out, mistreat animals, and fight with other children without facing consequences. As she grows, she becomes an object of desire but remains misunderstood. The book then introduces a series of women who are misjudged by men: Becky is left abandoned, her fate uncertain; Carma's husband hastily doubts her faithfulness, driving her to attempt suicide; Fern mesmerizes the narrator, who is neither aware of nor questions his obsession; Esther is ridiculed by the man she admired for years; and Louisa is reduced to a status symbol for two men who fight over her, disregarding her true identity.

The second section of the book features more interaction between genders, with men longing for women they feel they cannot possess. This section highlights missed connections and failed romances caused by misunderstandings about each other. A prominent example is "Box Seat," where Dan Moore feels compelled to shield Muriel from a society he believes will take advantage of her gentle nature, leading him to behave overly assertively. The central symbol here is Mr. Barry, a dwarf who, despite boxing himself to exhaustion, serenades a woman with a lovely song and a rose. Barry's diminutive stature underscores the absurdity of Dan's macho posturing. By the section's end, Bona and Paul stand out as the most balanced couple, demonstrated by their equal partnership on the basketball court. However, their relationship ultimately fails due to Paul's insecurities about his race.

The story of Kabnis scarcely addresses gender roles. Stella and Cora, the prostitutes, manipulate the men in their lives as much as they are manipulated. Carrie K. emerges as one of the book's most sensible characters: amidst disappointment, she recognizes the dignity of the past that others wish to escape. The book, which begins with a woman viewed merely as a sexual object, concludes with a depiction of a sensitive and insightful woman.