David Foster Wallace’s demanding book Infinite Jest (1996) uses its information-heavy structure to unsettle the reader with repeated constructions of separation and return. Endnotes, meta-commentaries, non-linear plot chronologies, and extended gaps between narrative threads work to separate the reader from the primary thrust of the plot, presenting the reader with a choice to return to the original narrative whenever they are equipped. Once the reader’s sense of linearity is disrupted, Wallace’s repeated use of separation and return encourages the reader to actively participate in the construction of meaning out of an abundance of data. The first section of this article summarizes the history of “moralizing” in 20th century fiction, where innovators such as Vladimir Nabokov, John Barth, and Thomas Pynchon challenged conventional views on the social function of the novel and raised important questions about the “authority” of the author. Late postmodernist (or “post-postmodernist”) authors such as Jonathan Franzen, Haruki Murakami, and David Foster Wallace re- re-imagined postmodernist experimentations by employing more sophisticated narrative styles to point a reader towards recognizing his or her own moral responsibility to the world. The second section of the article examines the moral imperatives and structural guideposts presented within Infinite Jest and seeks to explicate the book’s moral center. The article compares Wallace’s neo-didactic style to the artistic theories of “epic theatre” and “the Distancing effect” developed by the German playwright Bertolt Brecht. Influenced by the modes of Brecht and others before him, Wallace’s central instruction is that the only way to safely escape the self through the act of dedication is to dedicate oneself to something that can mutually reciprocate and redeem the devotion. This understanding of mutuality in Infinite Jest represents a new definition of a postmodern novel, one that demands participation and synthesis from the reader if it is to succeed as morally instructive.