A Supposedly Fun Thing I’ll Never Do Again explores various types of alienation and detachment. In the opening essay, Wallace describes his childhood in the American Midwest. He played competitive junior tennis before he was no longer able to compete against his peers. This formative experience of junior tennis in the Midwest is a key part of Wallace’s identity; he still clings to his Illinois roots and his love of tennis when thinking of what it means to be David Foster Wallace. Over the ensuing essays, however, he explores the alienation he feels from these nostalgic childhood memories. The boy who played tennis beneath a tornado returns to Illinois to visit the state fair and, after years away, he feels like an outsider. The years spent playing tennis as a youth imbued Wallace with the idea that he was something of a competitive talent; however, watching the professionals at the Canadian Open up close, he realizes that he is extremely far from matching even a modicum of their talent. Wallace regarded himself as a Midwesterner and a tennis player but, as he grows older, feels alienated from these formative memories. He is detached from them in a meaningful sense and, through this process of alienation, loses his sense of self.