A sixteen-year-old boy from Cincinnati who moves to Winesburg with his grandmother. Despite having a rough upbringing and losing both of his parents, Tom is a soft-spoken, observant boy who is easily made happy and is well-liked by everyone in town. His shy, sweet nature makes him lonely and somewhat naïve, and he is resistant to sex and other adult aspects of life. Tom gets drunk for the first time in an attempt to connect with the suffering that he sees in other people. George Willard helps Tom during his drunken stupor and Tom claims that he slept with George’s love interest Helen White. He later admits that this is not true, but that he feels as though he did sleep with Helen and that getting drunk has taught him valuable life lessons.