I examine David Foster Wallace’s Infinite Jest, looking at the ways in which it speaks to our current cultural moment. I posit that Wallace, in the novel, is able to use his story to comment on the ground-clearing nature of irony, technological abstraction, and postpostmodernism, and suggest that the post-postmodern future makes individuals catatonic. I also argue that Wallace predicted many of the ironic features of post-postmodernism because he lived and wrote in a generation that came after postmodernism. Wallace identifies TV as quintessentially post-postmodern, where meaning is neutralized through a Fredric Jameson's idea of pastiche--a kind of irony that only seeks to reference itself. The opening scene of Infinite Jest shows a young man unable to speak to adults, and unable to extoll his virtues. Hal, the main character in the scene, loses his ability to speak. And if readers take Hal’s metaphorical catatonia a step farther, they will see a Hal representative of a millennial generation, also unable to speak. Hal is a post-postmodern child, buried by a culture of irony and Jameson's pastiche and depthlessness, where diatribes on metaphysical aboutness are more important than the meaning of things themselves. Wallace defines this problem, in the novel, as a central obsession and avoidance of the cultural feeling of "anhedonia," the radical abstracting of things that were once full of meaning of affective content. Soren Kierkegaard also defines this problem as "infinite absolute negativity," where individuals can become purely ironic and absent from society, gaining a kind of perverse negative freedom. On the other hand, the novel, I argue, not only posits the tyranny of this newfound perverse freedom in Western culture, but also laments the backlash of overt sincerity that is equally oppressive, represented by the AA parts of the novel. In end, I argue Wallace's novel laments the fact that we are losing something essential human when it comes to making our own choices about what to believe in, in our contemporary age.