The collection chronicles the formative years of two distinct protagonists as they navigate the social hierarchies and personal ambitions of early 20th-century American life. Basil Duke Lee serves as a fictionalized mirror to the author's own youth, moving from childhood in Buffalo to the threshold of Princeton University, while Josephine Perry acts as his counterpart, exploring the complexities of young womanhood during the same era. These stories utilize a traditional third-person narrative framework to examine the internal growth and external pressures faced by the characters. The physical world is defined by the rigid social expectations of the Jazz Age, where status and reputation dictate the success of the protagonists' social maneuvers.

Readers and critics often observe that these stories provide a window into the author's creative process and his preoccupation with the themes of youth and social aspiration. Discussion frequently centers on the contrast between the two protagonists, noting how their individual experiences reflect the gendered expectations of their time. Many highlight the technical proficiency of the prose, which maintains a consistent tone despite the stories being written over several years. The collection is often praised for its ability to capture the specific atmosphere of the pre-war era without relying on excessive sentimentality. Scholars frequently note that while these stories were intended as a cohesive work, they function effectively as a series of character studies that illuminate the author's broader literary concerns.