The aim of the paper is to analyze the novel Infinite Jest by David Foster Wallace through the lens of feminist theory, queer theory, and general notions on how to write about diversity. The main thesis is that Wallace used popular tropes in the 1990s and introduced a whole range of diverse characters, but he did it unsuccessfully. He was not inherently racist or sexist, but his understanding of diversity was lacking. It is obvious that he wrote about fringe characters from his privileged position without spending time with members of those communities. Characters that are not a part of the white and male group are usually ridiculed and shamed. A female character who crosses the boundary between femininity and masculinity is not praised but punished and hated because of that. Others are mocked because they do not present a perfect stereotypical image of what they are appropriating. Body dysphoria is also made fun of. Infinite Jest is not about diversity and those issues take a small percentage of this otherwise huge novel. However, Wallace introduces these topics and he is not being careful about how he is presenting them, which should be kept in mind while reading.