Seth Richmond, a teenage boy in Winesburg, lives in a large house with his mother that was once the grandest place in town but whose glory is now “somewhat dimmed.” After his father is killed in a street fight, Seth finds that his inheritance has been lost in bad investments. He and his mother Virginia must now survive on the income she makes as a court stenographer. Virginia is a timid, naïve woman who finds herself unable to discipline Seth even when he runs away with his friends for a week.
The death of Seth’s father has had a significant impact on the Richmond family’s sense of structure and normalcy. In the midst of the grief and disruption that the loss has caused, Seth is floundering without a fatherly presence to discipline him. His mother, though a devoted parent, is unable to reign in Seth’s rebellious behavior as he grows older.
Seth is a quiet, lonely boy who wishes he could join the other teenagers who laugh and joke together on their way to pick berries in the fields. The townspeople view Seth as a sullen, deep thinker, instinctively respecting him as they did his father and believing that he will move on from Winesburg to better things. Seth, however, feels that he has no underlying purpose or plan. He is envious of his friend George Willard, whose job at the Winesburg Eagle gives him a path in life and “a place of distinction” in the community.
While the people of Winesburg value and respect Seth as an individual, he tragically does not perceive the affection they feel toward him. Instead, Seth often feels lost, alienated, and unable to relate to other teenagers. From Seth’s perspective, his close friend George Willard has found an external sense of meaning through his career path, while Seth has no underlying direction in his life. He resolves to leave Winesburg, convinced that he cannot grow up and make something of himself if he remains in his hometown.
One day, George tells Seth that he is writing a book and has resolved to fall in love with the banker’s daughter Helen White so that he can draw material from his own romantic experiences. Since Seth knows Helen better, George asks him to tell her that George is in love with her. Seth, who also has feelings for Helen, is resentful of George and decides to talk to her, but not about George.
George is under the impression that he must gain life experience in order to be an effective writer, and that falling in love is a crucial element of manhood on which he is missing out. Although he and Seth are close, George is seemingly unaware that his good friend also has feelings for Helen White.
Walking around Winesburg, Seth feels envious of George’s rapport with the same townspeople from whom he feels alienated. He goes to Helen’s house and tells her that he will leave home and move to Columbus to work or go to university, and that George Willard is in love with her. They go on a walk and Helen holds Seth’s hand. Seth soon regrets his decision to get out of Winesburg because Helen has had a crush on him since they were children. He hastily imagines a future with her and hopes that she will talk him out of leaving. Instead, Helen encourages him to go and runs off. Seth leaves feeling convinced that George will find love but that he never will.
Still feeling uncertain and directionless, Seth tells Helen that he plans to leave Winesburg in order to test her feelings for him. Although he is unsure of what his path in life should be, he is disappointed when Helen encourages him to go rather than objecting. This interaction deepens Seth’s envy for George as he becomes convinced that his friend is destined to find love while he is bound to be alone forever.