Loneliness is examined partially as a consequence of miscommunication and the inefficiency of language in several of Wallace's works, including, but not limited to, the novels The Broom of the System and Infinite Jest, as well as short stories such as Good Old Neon.
In Good Old Neon Wallace spends a significant portion of the story commenting on how "it could easily take a whole lifetime just to spell out the contents of one split-second's flash of thoughts and connections" with words (151). This overwhelming quantity of thoughts and feelings leads us to create a very loose estimation of our mental states with the words that we share with one another. This desperate but futile attempt to share who one is causes feelings of loneliness and fraudulence.
Wallace also seems to suggest that loneliness arises from the difficulty of the Self and Other dilemma and our society's growing dependence on entertainment, specifically television, over human interaction.