Much of Enoch Robinson's story takes place in New York City, but "Loneliness" belongs in Winesburg, Ohio for two reasons. First, Enoch Robinson is, like most of the people of Winesburg, a lonely person. In his case, his loneliness is caused partly by his devotion to art. At twenty-one, he fled Winesburg hoping to find a place where he would fit in better, but he doesn't feel that he belongs in New York City either. As Anderson says, Enoch "couldn't understand people and he couldn't make people understand him." Therefore Enoch has locked the door of his rented room and peopled his isolation with phantom creatures of his imagination; he is isolated by his art arid with his art; he is another lonely grotesque.
Another reason that "Loneliness" belongs with this collection of stories is that Enoch, at thirty-six, returned to Winesburg, and the last part of his story is a long explanation to George Willard of his return. We learn that Enoch deserted his art after a time in the city. He married, became a voter and a working man; "he got a job in a place where illustrations are made for advertisements," says Anderson, making it sound like something despicable and demeaning. We are told, "Two children were born to the woman he married," as if Enoch weren't involved. And, indeed, he wasn't really. Enoch was playing a role and he began to feel choked and walled-in by his apartment. So Enoch left his wife and went back to his rented room. There, however, he met another woman who eventually left him and took all of his imaginary phantoms with her. So Enoch returned to Winesburg, frustrated and defeated.
In this story, Anderson is apparently trying to show us what an artist is like. He describes Enoch as a "boy-man" because Anderson himself was apparently enough of a romantic and Platonist to think that a child is more sensitive and imaginative than an adult. The woman who drove Enoch back to Winesburg is described as being "too big for the room" and "so grown up." It was she, this personified adulthood, who took all of his "people" away. All that is left of Enoch is "a thin old voice" complaining, "It was warm and friendly in my room but now I'm all alone."
One realizes if he reads this story carefully, its strength is in its subtlety and its suggestiveness. Take, for example, what seems to be an irrelevant detail-that Enoch was hit by a streetcar and was made lame. But is such a detail irrelevant, or is Anderson suggesting that industrialization and mechanization is likely to destroy the artist — or at least maim him? Or consider the fact that Enoch's cheap rented room is "long and narrow like a hallway." Is Anderson suggesting that the room is impractical and uncomfortable, or is he intimating that the artist's world is a magic place that leads him to new worlds, a hall that has many doors to open.
As one begins to speculate about Anderson's subtlety, he may remember Enoch's description of one of his paintings: "The picture you see doesn't consist of the things you see and say words about. There is something else, something you don't see at all," and as Enoch talks about this painting, one begins to realize that what he put in the picture is less important than what he left out. Anderson himself cultivated the art of leaving out.
In this story we see young George Willard listening eagerly to Enoch Robinson, even urging the old man to continue his story. George's sympathy and interest at this point in the book contrasts with his fear of getting involved with Wing Biddlebaum. We realize that George is maturing, that he is beginning to follow Kate Swift's advice about finding out what people are thinking about. George is trying to prepare himself to be a writer.