The present article attempts to contribute to both Fitzgerald scholarship and nostalgia studies by examining how text, illustration, and advertisement enter into dialogue in the original magazine format of F. Scott Fitzgerald’s short story “The Rich Boy”. As research is still scarce on Fitzgerald’s stories as they were first published, this field may hold new, potential research paths for this canonical author, a few of which I endeavor to explore here. This paper suggests that this 1926 magazine version offers a unique nostalgic experience that differs from the reading of Fitzgerald’s text in an image-free anthology. It argues that, with some exceptions, these media generally interact in a cohesive way that echoes or reinforces a nostalgic mood. Niklas Salmose’s typology of nostalgic strategies will be used to draw out the nostalgia in these media, and an intermedial approach will be employed to investigate how they engage in nostalgic dialogue.