Basil and Josephine charts the coming of age of two privileged youths from quiet Midwestern towns, Basil Duke Lee and Josephine Perry - based on Fitzgerald himself and a combination of his first love Ginevra King and his wife Zelda. As one struggles to gain the acceptance of his peers and becomes consumed by ambition, the other finds herself obsessed by teenage crushes and has to confront the pitfalls of popularity.

Written for the Saturday Evening Post while the author was working on Tender Is the Night, these stories form a realistic and entertaining portrait of two young adults in the 1910s, fascinating both for the autobiographical insights they provide and the timeless satire that Fitzgerald's fiction has become synonymous with.