"Loneliness" is the story of Enoch Robinson. Born in Winesburg, he moves to New York as a young man and falls in with a circle of artistic types. Eventually, though, he grows tired of them, because he possesses a kind of childish egotism that makes him unable to tolerate other people--save imaginary ones, who always agree with him and never threaten his self-image. He grows lonely after a while and gets married, in an attempt to lead a normal, respectable life, but the same self-centeredness afflicts his marriage, and eventually his wife leaves him. She considers him a little bit insane, perhaps justifiably, since after she leaves, Enoch moves back into his own apartment and busies himself with his large, ever-growing collection of imaginary friends. He is happy for a long time, but eventually something goes wrong. Enoch meets a woman in his apartment building, and she comes to visit him. One night, he tells her all about the "people" who live in the room with him, and after a long time, she seems to understand. When she leaves, however, all the imaginary people follow her out the door, never to return. He has been alone ever since, he tells George Willard while relating this story years later, having left New York and returned to Winesburg.
The main character in "An Awakening" is Belle Carpenter, a bookkeeper's daughter who works as a milliner's assistant in Winesburg. Ed Handby, a local bartender, is courting her awkwardly; so far, they have spent only one evening together. Still, he insists that they will be married. Meanwhile, though, she has been going out for walks at night with George Willard, even though she prefers Ed. One evening, while wandering about town in an introspective mood, George senses himself having an epiphany, and he takes Belle out for a walk and tries to impress on her that he has become "different." He is suddenly convinced that she will "surrender herself to him," because of the change that has come over him. But while he is kissing her, Ed Handby comes upon them, shoves him aside, and moves to take Belle Carpenter away. George tries to fight him, but the bartender knocks him over into the bushes and drags the girl off. Humiliated and unhappy, George makes his way homeward, noticing that all the magic has vanished from an evening--and a town--that now seem "squalid and commonplace."
"Loneliness," the title given to Enoch Robinson's story, could be applied just as easily to most of the stories in Winesburg, Ohio. The title acquires a particular poignancy in this case, however, because Enoch once possessed the kind of companionship that his fellow townsfolk desire so ardently, only to see it slip away. By depicting the companionship of unreal, hallucinatory people, Anderson may be hinting that the only cure for loneliness is in the world of one's own mind. Still, it is a fragile, transitory cure, since Enoch's visions are easily destroyed by contact with the real world. His cloud of imaginary friends keeps him company only so long as they are the most important things in his life. Once a real person--his female neighbor--begins to matter to him, his companionship evaporates. Once he tries to unite the real and unreal worlds by telling the girl about his cluster of imaginary friends, his hallucinations leave him, following the girl out the door. Enoch's consequent loneliness is perhaps worse than that of any other Winesburg inhabitant, since he lives with a perpetual sense of loss, of a vanished paradise.
"Awakening" is an ironic title for the story of Belle Carpenter--which is really the story of George Willard. The odd relationship between Belle and Ed Handby, who seems to be her true love despite his inability to do anything but bark orders at her, serves principally as a vehicle for Anderson to illuminate one of the false epiphanies of adolescence. Wandering through the darkened town, George Willard believes himself to have become enlightened, to have taken a jump forward into adulthood. Everything suddenly appears different to him, and he feels that his inner self has matured. But when he tries to convey this revelation to someone else--Belle--the result is dull boasting, for which Ed Handby quickly humiliates him. George realizes that his epiphany was empty, and his mood swings rapidly from exultation to sour depression. He is a victim, like most adolescents, of the gap between his own illusions about himself and a world that often seems designed to shatter those illusions.