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Fitzgerald’s engagement (some even say obsession) with his era’s changing attitudes toward youth and gender is prominent in much of his work. “Bernice Bobs Her Hair,” published in 1920, is no exception. Employing the theoretical framework of the female Bildungsroman—the female narrative of development—this article presents a contextualized reading of the story as an early study of flapperhood, of modern perceptions of youth and maturation, and of the process of female socialization, revealing Fitzgerald’s complex relationship with the ideal he and his wife so helped to advance. Studying the story’s engagement with the larger literary and ideological debates that this genre participates in offers a deeper understanding of Fitzgerald’s depiction of the process of socialization that calls into question previous assumptions about both maturation and femininity. Moreover, this analysis engenders an alternative reading of the story’s ending, which further problematizes Fitzgerald’s portrayal of socialization into flapperhood.