In his frequently anthologized short story "The Sky Is Gray," Ernest J. Gaines presents a fictionalized account of a series of events that occurred in 1940s Louisiana when he was a mere boy suffering with a bad toothache. This physical ailment serves as a narrative catalyst, both driving the action and pulling the readers into a world where poverty co-exists with pride, and in which a mother who appears to be cold and unfeeling is revealed to be a loving parent teaching her male child to negotiate the often harsh realities of the segregated South. Gaines's ability to recreate the Louisiana parish that was the backdrop for his initiation into manhood is impeccable. However, in a lesser-known work, "Getting the Facts of Life," Paulette Childress White is equally impressive in her ability to evoke the streets of metropolitan Detroit, the challenges faced by a welfare-assisted Black family in the 1960s, and a young girl's encounter with the various challenges impending womanhood could hold for her. This article explores the pedagogical rationale and strategies for teaching these stories as companion pieces. Placing these two stories in tandem provides an excellent opportunity to underscore differences in male and female literary voices and issues and to explore the contrasts between the concerns of a child in the rural South of the 1940s and a child in the industrial North in the 1960s, while expanding the general notion of what constitutes a coming of age story.