"Queer" is concerned with Elmer Cowley, a newcomer to Winesburg, whose father has opened a store selling various curiosities. The business is unsuccessful, and Elmer is convinced that the whole town thinks that the Cowleys are strange and that everyone is secretly laughing at them. He becomes belligerent and slightly unhinged, and shouts at his father and a traveling salesman in the shop. After this incident, he takes a long walk into the country, all the way out to what used to be the Cowley farm, to tell his troubles to a retarded man who used to work for his family. Still dissatisfied, Elmer stalks back to town, where he singles out George Willard as representative of Winesburg's scorn for the Cowleys. Additionally, he doesn't believe that George has ever been unhappy in the way that he himself constantly is, and thus feels alienated. Elmer attempts to harass George, and then robs his own father, intending to take the money and run away to the city. At the train tracks, Elmer runs into George again. He tries to explain himself but fails; he then gives the money he stole to George. Suddenly, and without provocation, Elmer attacks George, knocking him out cold. He jumps aboard a passing train and rides away from Winesburg.
In "The Untold Lie," two farm laborers are working together in a field. One, Ray Pearson, is a serious man with a wife and six children. The other, Hal Winters, has a reputation as a fighter and a womanizer. Hal confides to Ray that he has gotten a girl pregnant, and wants to know if he should do right and marry her. Oddly, Ray cannot manage to formulate a reply, and when he goes home that night he feels a tremendous bitterness about his own marriage, which likewise came about through an unwanted pregnancy. He has an urge to tell Hal not to get married, to stay free at whatever cost, and suddenly runs out of his house to find him. When Ray finds Hal, though, his voice fails him. Hal is very cheerful, and says that he has decided to marry the girl. As Ray walks home, a pleasant memory of his children seems to come to him, and he realizes that whatever he would have told Hal, "it would have been a lie."
"Drink" introduces Tom Foster, a boy who moves to Winesburg with his grandmother after his parents die. Tom is a gentle, well-liked boy who never asserts himself, preferring to stay in the background. He is too forgetful to hold steady employment, but works odd jobs, and is made happy by small things. One night, he decides to get drunk just to see what it feels like. This incident occurs at a time in which he is in love with Helen White, the daughter of one of his employers. He buys a bottle of whiskey and sits on an embankment in the spring air, drinking and enjoying his intoxication. Eventually, George Willard happens by, and Tom starts babbling about Helen White, telling George that he has made love to her. George, who has feelings of his own for the girl, tries to quiet Tom, but Tom takes his hand and tells him that he is glad to be drunk because it has taught him something and allowed him to suffer like everyone else.
Like Seth Richmond, Elmer Cowley is a foil for George Willard. He is insecure about his position in Winesburg, and he focuses his anger on George because George seems to be happy and in tune with the spirit of the time. But while Seth seems more mature, at times, than George Willard, Elmer Cowley is a childish figure. His temper tantrums, his penchant for petty theft, and his strange paranoia make him seem immature and even slightly deranged. Anderson uses Elmer's experience to illustrate the confining nature of small-town life for those who are considered "queer." Elmer does not envy George Willard's gifts, or his wealth, or his good looks. Rather, he envies the fact that George "represented in his person the spirit of the town." Public opinion extols George while ridiculing Elmer and his family. In acting violently toward George, Elmer is doing what little he can to strike back against the confining force of "the judgment of Winesburg," and in that violent action is fortifying the town's beliefs about him. In the end, Elmer can only escape the town's judgment by leaving.
"An Untold Lie," from its title onward, is a deliberately ambiguous story. Ray Pearson is given an opportunity to reflect upon his life, particularly upon his decision to get married at a young age. His reflections lead him to the conviction that he made a terrible choice, and that unhappiness has plagued him because of it. This can be read as another example of the extent to which public opinion forces characters to evaluate themselves, as in the case of Elmer Cowley. In this interpretation, Ray Pearson is a victim of a societal straitjacket, one that has imprisoned him in poverty and a loveless marriage. Yet at the end of the story, when Hal Winters decides to marry his woman, Ray suddenly changes his mind, and decides that his unhappiness with his marriage was nothing more than the "lie" of the title. He suddenly seems to have a "memory of pleasant evenings spent with the thin-legged children in the tumbledown house by the creek" where he lives, and makes his way homeward "into the darkness of the fields." Anderson leaves the reader to form her own opinion about whether Ray is truly unhappy or only temporarily dissatisfied, about whether Ray has been lying to himself. In either case, it seems clear that Ray himself is uncertain, and remains incapable of discovering the truth--if any truth exists.
Tom Foster, the main character in "Drink," is an eminently likable figure, easygoing and cheerful, unambitious and dreaming. His story marks the reappearance of Helen White, this time as an object of his longing. She appears only indirectly, as the principal character of his drunken reverie, in which "he had been with her on the shore of the sea and had made love to her." From the mind of another character, such a fantasy might hint at darker desires, but Tom Foster is the perfect innocent. More than anyone else in Winesburg, Ohio, he knows how to enjoy life, despite the simplicity of his surroundings. "The most absurd little things made Tom Foster happy," Anderson writes, and this quality of being easily satisfied makes him a pleasant antidote to his bitter, lonely fellow townsfolk; one senses that while Tom is alone, he is never lonely. His experience with drunkenness offers the key to his character. "I wanted to suffer I thought that's what I should do because everyone suffers," he tells George Willard, revealing a deep-seated desire to be like everyone around him. Like so many others in Winesburg, Tom feels alienated from society; his sense of estrangement, however, arises not out of unhappiness, but rather out of an excess of happiness. He embraces the misery that others routinely experience because he wants "to learn things" about life, and hence lessen his feelings of alienation.