"Adventure" tells the story of Alice Hindman, who is twenty-seven, clerks at Winesburg's dry goods store, and still lives with her mother. Alice, we learn, was once the lover of a young man named Ned Currie, and after he went off to seek his fortune in Chicago, she remained faithful to him. For a long time, he wrote every day, but eventually he became swept up in his new life and forgot her. Now, ten years later, Alice still carries a torch for him. She feels herself getting older, but she cannot imagine herself marrying anyone but "Neddie." Eventually, she joins the local Methodist Church and attends weekly prayer meetings in order to break the dull routine of her life. Still, she feels a restlessness taking hold of her and a desperate need to be loved. One rainy night, she comes home from work and goes upstairs to get undressed. Seized by a strange urge, she runs outside in the rain naked and accosts an old man who is passing on the sidewalk. Suddenly ashamed, she rushes back inside and lies down to face the wall and accept "bravely the fact that many people must live and die alone."
"Respectability" centers around Wash Williams, the telegraph operator in Winesburg. Hugely obese, filthy, and defiantly antisocial, he has no friends in town, and particularly despises all women, calling them "bitches." Seeing George Willard out walking with a girl one day, he takes the young reporter aside and tells him his story. Once, he was a successful, good-looking young man, running the telegraph office in Columbus, Ohio. He had a wife and loved her very much, only to discover that she was cheating on him with a number of men. He left her immediately, but after several months the girl's mother invited him to their house in Dayton, trying to help the couple reconcile. She told Wash to sit in the parlor, and then sent his wife, stark naked, in to see him. Shocked, the telegraph officer attacked his wife's mother with a chair. Since then, he has had nothing to do with women, considering them to be uniformly depraved and deceitful.
"The Thinker" concerns Seth Richmond, the son of a family that has fallen on hard times since the father's death. Seth is so clear thinking and sensible that even when he runs away for a week, hitching a ride on a box car, his mother is unable to bring herself to punish him. Seth is friends with George Willard, and one summer evening he and George sit together and talk in the Willard boarding house. George declares his intention to fall in love, and settles on Helen White, a local girl, as the object of his affection. He asks Seth to tell Helen, but Seth becomes flustered and leaves. Seth wanders about for a while, feeling alienated, and ends up at the White's house, where he invites Helen out for a walk. As they walk, he tells her that he plans to get out of Winesburg, either by going to college or getting a job. There is romantic tension between them, but it dissipates amid mutual awkwardness, and Seth is left thinking about how Helen will probably end up in love with "some fool some one like that George Willard."
The unhappiness of women, both married and unmarried, is a persistent theme in Winesburg, Ohio, running through the lives of Elizabeth Willard, Louise Bentley, and Kate Swift. Amid this company, Alice Hindman is a rather predictable specimen. Her section is one of the few places in the novel where Anderson makes use of a stereotype instead of creating an authentic character. Her nude adventure on a rainy day notwithstanding, Alice is little more than a typical old maid, unmarried and unhappy because of her solitude. Even the explanation for her old maid status is formulaic--when she was younger, her supposed "true love" left town, abandoning her. There is little depth in the book's treatment of Alice's loneliness, a manifestation of the fact that she is not considered a strong individual.
By way of contrast, Wash Williams's chapter shows how Anderson can take another stereotype--that of the man who hates women because his wife has left him--and reinvent it in startling ways. Williams's misogyny, it is implied, is secretly shared by many men who are not brave enough to express it. Among them is his superintendent at work, who receives a complaint from Mrs. White, the banker's wife, about how filthy Williams's office is. "When he received the letter he tore it up and laughed unpleasantly. For some reason he thought of his own wife as he tore up the letter." If, as this scene suggests, Williams is an icon of misogyny, the pureness of his sentiment is embodied in the richness of the language he pours out in abuse of females. "My wife is dead as all women are dead. She is a living dead thing making the world foul by her presence Ugh! They are creeping, crawling, squirming things, they with their soft hands and blue eyes." Aspects of female beauty disgust Williams, as they serve only to conceal a woman's fundamentally repugnant nature. The zealousness of his misogyny seems to have its roots not in the initial fact of his wife's affairs, but in the surreal scene in which his mother-in-law tries to bring the couple back together by sending her daughter in naked to see Wash Williams--as if a little sex were all he needed. His hatred of women may have begun with his wife's infidelity, but it is this stark, calculating act that transforms him, leaving him thoroughly convinced that women are dishonest, shallow, and base creatures.
"The Thinker" draws back from the lives of Winesburg's older people, and into the realm of adolescent yearning. Seth Richmond is a much deeper person, in many ways, than his successful, intelligent friend George. He is more sensitive--and also moodier--as his reaction to George's superficial decision to "fall in love" with Helen White indicates. Ultimately, he proves more grown-up, both in his authentic, heartfelt sentiments for Helen (who is a recurring target of the longing of young male Winesburgers), and in his readiness to leave Winesburg. His impatience with the town, however, is not just a mark of maturity. It also stems from the fact that he feels overshadowed by George--which he is, both in the estimation of the townspeople (although not, perhaps, in the eyes of Helen, who seems to care for him), and in terms of Anderson's overall structure for Winesburg, Ohio. When Seth complains that "George Willard belongs to this town" in a way that he himself does not, he is stating what the reader already knows--that this is George Willard's book, and not Seth Richmond's.