David Foster Wallace’s unique writing style hinges on difficulty. His approach to storytelling challenges the reader’s expectations, forcing them to actively engage with the characters and scenes rather than passively observing the story. Wallace developed this method because he was bothered by the societal tendency to encourage passivity; in a sense, his fiction is a wake-up call, pointing out modern problems and begging us (the readers) to acknowledge their existence. By writing authentically about American culture—specifically the challenges of living in a consumerist age—Wallace creates a bond between himself (as an author) and his readers: a community is forged. Struggling with clinical depression for most of his life, Wallace knew the pitfalls and hopelessness associated with loneliness. In other words, he knew the difficulties that arose from these intense feelings of isolation. In his first short story, “The Planet Trillaphon As It Stands In Relation To The Bad Thing”, Wallace provides a detailed assessment of how difficult depression is. I analyze this story partially because I find it to be understudied in current scholarship, but chiefly because Wallace envisions unadulterated empathy as a key answer to the difficulty of loneliness. Ultimately, I argue that empathetic communities are a life-line, allowing members to admit in safe spaces that life is difficult so that they can be affirmed and push past their struggles. Wallace’s difficult style is one type of empathetic community; sharing his pain through fiction helps others recognize they aren’t as alone as they feel. By focusing my argument on this story, I aim to prove that Wallace’s earlier work is more than worthy of our attention and that contemporary difficulties such as loneliness cannot (and should not) define us.