Charley Edwards
Charley Edwards is a young actor and the "leading juvenile" of a Pittsburgh stock theater company. He is also a friend of Paul's and fuels Paul's fascination with the theater. Charley invites Paul to the company’s Sunday rehearsals and permits him to spend time backstage. When Paul's academic situation deteriorates and his father forces him to work, Charley "remorsefully" vows not to see Paul again. After Paul runs away from home, Cather reveals that Charley had assisted Paul in planning his trip to New York.

Paul
Paul is the main character of the story. A "motherless lad," he was born in Colorado, where his mother passed away from an illness during his infancy. He is a thin, pale, and dreamy teenager who feels a strong need to distance himself from his mundane surroundings in Pittsburgh. While those around him focus on earning a living and advancing socially, Paul is drawn to the glamorous world of music, theater, and art. He yearns for the beauty that money can buy but despises the monotonous and harsh reality of daily life. After his persistent lying, failure to complete schoolwork, and "insolent" behavior result in his expulsion from school, Paul steals from his employer and escapes to New York City. There, he fulfills his dreams by purchasing expensive clothes, staying at the luxurious Waldorf Hotel, attending the opera, and becoming "exactly the kind of boy he had always wanted to be." When his theft is discovered, Paul cannot bear the thought of returning to the "ugliness and commonness" of Cordelia Street and ultimately commits suicide by jumping in front of a moving train. Cather's portrayal of Paul is ambivalent, leaving readers to ponder whether Paul chose his tragic end willingly. While Paul's alienation from his environment is evident, it remains unclear whether his fate is a result of environmental determinism or the folly of youth, a dreamer who died with "all his lessons unlearned."

Paul's drawing master
Paul's drawing master is the most empathetic of his teachers. He notices that Paul seems troubled and suggests that none of them truly understands the boy. He remarks on Paul's mother's early death and states that "there is something wrong about the fellow." Through his perspective, the reader observes Paul's pale complexion, with his face "blue-veined" and "drawn and wrinkled like an old man's about the eyes."

Paul's father
Paul's father, a widower, holds a significant position of authority in Paul's life, embodying the principles of hard work and the "American Dream" that Paul detests. He is employed by a railway company and harbors "a worthy ambition to advance in life." He aspires for Paul to emulate one of their neighbors on Cordelia Street, a young man who serves as a clerk for one of the "iron kings" of a steel corporation. He is worried and "perplexed" about his only son: he contacts the principal's office after Paul gets suspended, repays Denny & Carson the thousand dollars Paul stole, and travels to New York in search of Paul after he runs away. To Paul, however, his father symbolizes oppressive authority and the monotonous middle-class existence of Cordelia Street. Paul dreads coming home late to face his father, "the figure at the top of the stairs," with his "inquiries and reproaches."