Chapter 1 of Chinese Handcuffs opens with a letter Dillon Hemingway is writing to his older brother Preston. Preston has committed suicide by shooting himself in the head, but Dillon is desperate to talk to someone about the turmoil he is going through, and chooses his brother, even though he is dead. Dillon, like his brother before him, has an angry, rebellious nature, and is constantly in trouble at school. He remembers that everyone used to say that he and Preston were so much alike, but Dillon knows that things were always much harder for Preston, who had a more brooding personality, especially after he lost his legs in a motorcycle accident. In his letter, Dillon tells Preston that, although he loves him, he thinks he took the "cowardly way out" by committing suicide.
Preston had left a note for Dillon before he died, telling him to never forget an incident from their childhood when they brutally killed a neighbor's cat. The incident scarred both boys deeply, because it revealed to them so starkly "the horror in (them)selves." The boys had vowed never to tell anyone what had happened, but after Preston's death, Dillon had confided in his friend and Preston's former girlfriend Stacy. Stacy had acknowledged that "human beings are connected by the ghastly as well as the glorious," and spoken of the necessity to always guard against allowing the evil side of one's nature to take control.
Chapter 1 closes with Dillon again talking to Preston, telling him about the two women in his life, Stacy and Jen. Although Dillon is not in a romantic relationship with either of them, both are highly influential in his existence. As Preston's former girlfriend, Stacy is "big in (Dillon's) past," while with Jen, a classmate and star basketball player, Dillon enjoys a "magical sense of connection that goes beyond time and experience together." Both girls give Dillon the support he needs to get through these trying times.