A Supposedly Fun Thing I’ll Never Do Again addresses Irony and Society as a major theme. As a way of exploring the pervasive irony of American culture in the late 20th century, however, Wallace often uses irony (particularly situational irony) as a literary device to help make his point. In literary terms, irony emerges from the divergence between expectation and reality. This is found throughout the collection of essays, even in the title. The title posits that something is supposedly fun but that it is not something the author is ever willing to do again. This especially refers to the cruise Wallace takes in the final essay, which uses situational irony: The apparent luxury (expectation) of the cruise masks a deep psychological malaise (reality).

Situational irony likewise appears in the essay about the state fair, in which the rides and the food stalls should entertain Wallace but instead only disappoint him. Even when he meets someone he supposedly admires, such as David Lynch or Michael Joyce, Wallace cannot help but contrast his expectation of their character or work with a troubling reality that suggests a deeply ironic truth about society. Thus, Wallace uses irony as a literary device to explore the irony of the Postmodern society he inhabits.