Enoch Robinson, a man who grew up on a farm just outside of Winesburg, moves to New York City at twenty-one to attend art school and lives there for fifteen years. Although Enoch is talented and has an eccentric mind that would lend itself to creativity, his lofty plan to study in Paris with the masters never pans out. Enoch is very immature, and his inner child prevents him from fully understanding adult concerns like “money and sex and opinions.”
Enoch Robinson is an example of a man who escaped Winesburg in hopes of pursuing bigger dreams outside of his hometown. Though talented and motivated, Enoch’s perpetual immaturity leaves him unable to successfully integrate into the adult world.
The narrator points out that Enoch’s story is “the story of a room almost more than it is the story of a man.” When Enoch first arrives in New York, he has several chaotic experiences with alcohol and women that leave him confused. He makes a group of artist friends who come to his room in Washington Square in the evenings to discuss art and smoke cigarettes. Enoch stays silent in the corner during these gatherings, wanting to join the conversation but too excited to speak coherently. He especially wants to explain his paintings on the walls (many of which portray scenes from his old life in Winesburg) that his friends misinterpret.
The unsettling experiences Enoch has in New York reflect his childlike inability to regulate his own behavior or understand complex situations. Enoch is surrounded by friends, yet his immature, underdeveloped nature makes him unable to fully relate to his peers. Although he desperately wants to connect with them and discuss art, he cannot coherently express himself.
Enoch becomes so frustrated with his own inability to communicate that he decides he doesn’t need real people and invents imaginary friends instead. Enoch, according to the narrator, is a “complete egoist” like a child, and wants people he can selfishly control and boss around at his whim. But the imaginary friends do not quell Enoch’s loneliness, and soon he gets married to a woman he meets at art school, has two children, and gets a job at an advertising agency.
Enoch feels a deep sense of shame at his inability to interact with other people, and as a result he decides to create imaginary friends whom he can influence. While this temporarily satisfies Enoch’s need for socialization, he gets married and begins a career path, as he still craves a more conventionally mature lifestyle.
For awhile, Enoch is serious about playing the role of an adult and tries to be a productive, politically-aware citizen. But he begins to feel trapped by his life and family, lying for an excuse to go out on walks and secretly re-renting his old room in Washington Square. When Enoch’s mother dies and leaves him $8,000, he gives the money to his wife (who is afraid of him and thinks he is insane) and leaves her and their two children. Without his family, Enoch lives happily in his apartment with the company of his imaginary “shadow people.”
While Enoch is ostensibly committed to his role as a husband and father, it is only a façade that he maintains out of obligation. He begins to regress toward his old life and eventually cracks under pressure and abandons his wife and children. The loss of his family does not initially seem to faze Enoch, as he is content to go back to his alienated life with only the company of his imaginary friends.
Enoch, having returned to his hometown of Winesburg from New York City after fifteen years, decides to tell his story to George Willard. George is apprehensive due to Enoch’s unstable reputation, but Enoch can sense George’s introspective “youthful sadness” and believes that he will understand. Enoch tells George about a female acquaintance in New York whom he wanted to be with but scared away when he had a nervous breakdown and yelled at her. When the woman left, Enoch’s imaginary friends followed her out and he was left with no one. On the way out of Enoch’s room in Winesburg, George hears the man whimpering about being all alone.
Many years after he loses his family, Enoch returns to Winesburg because he has nowhere else to go. Like many of the other older men in town, he tells his story to George Willard because he perceives a quality in the young man that is both innocent and mature. Enoch’s ongoing dilemma between wanting to be left alone and yearning for human connection culminates in the loss of his female acquaintance and his imaginary friends. George, who thus far has been encouraged by several other characters to branch out and form relationships, is struck by Enoch’s tragic story.