Although these essays are not primarily about Wallace, he is an important character in almost all of them. Wallace grows up in the small town of Philo, Illinois, and spends most of his time as an adolescent playing tennis. Wallace is very good at tennis in his early adolescence because he exploits his natural understanding of geometry to return volleys until his opponents make an error or breakdown on the court. However, as Wallace's opponents develop faster physically than him, he discovers that this style of play is no longer successful. Wallace's roots in Illinois help to earn him a job covering the Illinois State Fair in 1993. Returning to Illinois, Wallace discovers that he is no longer a Midwesterner and has fully become an Easterner after his collegiate and post-graduate studies in the East. The article Wallace writes on the Illinois State Fair leads to the same magazine commissioning him to write an experiential essay about a luxury cruise, which becomes the titular essay of the book.