One of the key insights Sherwood Anderson develops in Winesburg, Ohio is the idea that all people are fundamentally lonely, but each in their own unique way—idiosyncrasies Anderson calls the “grotesque.” Many of the stories are directly concerned with capturing the precise nature of the focus character’s loneliness and identifying the grotesque parts of their inner worlds that prevent them from forming meaningful connections withing their community.

Anderson’s thematic exploration comes to a head in “Loneliness,” in which Enoch Robinson identifies the source of his loneliness as a fatal flaw: his inability to engage with anyone other than himself. Enoch spends most of his days in a room, preferring the company of imaginary friends to that of friends whose thoughts and opinions may allow him to develop more nuanced ideas about the nature of art. He sabotages his last chance at a meaningful relationship by scaring off a neighbor who seems content to sit with Enoch in silence. Even when Enoch’s neighbor poses no resistance to his opinions, he feels her presence impinges on his thoughts like a threat. When she leaves, Enoch sees his imaginary friends leaving with her, revealing to him the full terror of his loneliness. His obsession with his own inner world makes it impossible to connect with anyone, leaving him completely alone.