Tom Foster, a sixteen-year-old boy from Cincinnati, moves to Winesburg with his grandmother after his mother and father die. Tom’s grandmother, who had an adventurous youth, steps in to raise him after his parents die but is worn out physically and emotionally. The old woman was raised near Winesburg and insists that she and Tom move there using some money that she finds on her way home from work. On the train ride to Winesburg, Tom’s grandmother tells him stories of her childhood there. She only reluctantly gets off the train when she realizes that the rural farm community in which she grew up has expanded into a bustling town.
As a young man, Tom Foster has experienced a tragic life thus far. After losing both of his parents, he is left with his ailing grandmother who seems to be rapidly deteriorating. Having lived in Winesburg many years ago, his grandmother’s perspective of the town is unique—whereas most of Winesburg’s residents view the town as small, depressing, and devoid of opportunity, Tom’s grandmother only notices that the town has become more prosperous and metropolitan over time.
Tom Foster adapts well to life in Winesburg. He and his grandmother get jobs as servants for a wealthy banker’s family. Tom is a small boy who is sweet and gentle despite growing up in a rough, gang-infested neighborhood in Cincinnati. He is well-liked by nearly everyone and tends to stay quiet and fade into the background. Once, Tom had stolen money for food when his grandmother was ill and he was out of work. He was ashamed of the deed but felt that the experience had helped him “understand new things.”
Tom’s positive attitude and likable demeanor in spite of his troubled background suggests that he responds well to loss and adversity. Yet although everyone in Winesburg thinks well of him, he is still timid and isolates himself from other people. His reaction to stealing money implies that Tom is inclined to search for the deeper meaning behind his experiences rather than accepting things at face value.
Despite his good intentions and likable personality, Tom Foster is irresponsible. He loses his job as the banker’s stable boy because he does not take very good care of the horses nor remember to complete his chores. On errands, he gets caught up in listening to conversations and goings-on around him, feeling that he is “a part of and yet distinctly apart from” the community. After Tom loses his job, he rents an inexpensive room and spends most of his time lying around and thinking or visiting with his grandmother. Tom enjoys living in Winesburg and begins to do odd jobs around town. His ability to be made happy by simple things (such as the smell of freshly roasted coffee) endears him to the community.
Although Tom has lost both of his parents and been somewhat forced into growing up, he struggles to make the transition into becoming a responsible adult. Despite losing his job, he still maintains a positive attitude and his tendency to be made happy by life’s simple pleasures makes him lovable to those around him. Unfortunately, Tom does not seem to perceive this likable quality in himself and feels that he is more an observer of the community than an active participant.
During Tom Foster’s upbringing in Cincinnati, he was exposed to crime, sex, and the “ugliness” of life. Tom had once been tempted by a prostitute and was scarred and confused by the experience. He puts sex out of his mind altogether until he arrives in Winesburg and falls in love with Helen White. One night, Tom decides that he needs to gain the one-time experience of getting drunk and does so in a local saloon. He becomes drunk quickly and makes his way to a nearby bridge where he sits feeling dizzy and ill.
Tom’s experiences in Cincinnati have left him with a pessimistic view of adulthood and particularly of sex. Believing that he must grow up regardless, Tom decides to get drunk as a makeshift rite of passage.
George Willard finds Tom Foster wandering drunkenly around town and takes him into the Winesburg Eagle printshop. Tom tells him that he made love to Helen White by the sea, but George knows this is not true and angrily tells Tom not to slander Helen’s name. George sits with Tom for hours and takes him for a walk once he has recovered a bit. Tom tells him that being drunk has allowed him to think more clearly so that he will never have to resort to alcohol again. Feeling a strange motherly instinct toward Tom, George takes him back to the print shop.
Throughout George Willard’s encounter with Tom, George displays greater maturity despite the two boys being around the same age. Although Tom’s mention of Helen momentarily angers him, George feels a sense of parental endearment for the boy. George, who (unlike Tom) has a solid foundation of a close relationships and a career path, is a comforting voice of reason for Tom amidst his drunken stupor.
Tom Foster again tells George that he had sex with Helen, and George becomes angry. Tom puts his hand on George’s arm and tries to explain himself. He tells George that although he was happy, he had noticed that everyone else suffered. Tom decided to try alcohol in hopes of suffering and feeling what everyone else felt. He clarifies that he did not have sex with Helen but felt as if he had. Tom insists that he is glad he got drunk, because the experience taught him a lesson.
While people in Winesburg admire Tom for his happy-go-lucky demeanor, he feels that this quality is what alienates him from the Winesburg community. Tom’s drunken night is motivated by a desire to acquaint himself with the same suffering he believes everyone else feels, as that experience is what prevents him from relating to others.