Cal O’Shea-Wallace is a lonely, art-loving high schooler, and one of the three main protagonists of You’ll Be the Death of Me. McManus describes him as having “bright red hair” (79) and wearing “brightly patterned shirts” (5), causing him to stick out among his classmates at Carlton High School. Cal is an only child who has a close relationship with his dads, Wes and Henry. His dad Wes “knows way more about my social life than any self-respecting seventeen-year-old should allow” (24). Cal’s close relationship with his dads distinguishes him from Ivy and Mateo, who have more complicated parental relationships.

Cal is characterized by his status as a “serial dater” (24) and his love for art. At the beginning of the novel, Cal has just been dumped by his girlfriend Noemi, and he is already pursuing a new romance with Lara Jamison, his art teacher. Before Noemi, he dated a “competitive fencer” (196), and he has been in back-to-back romantic relationships “since ninth grade” (24). Cal’s need to be in a relationship worries his father who fears that Cal will “have a marriage certificate before a bachelor’s degree” (23). Cal’s romantic relationship with Lara motivates his actions throughout the novel, as he tries to keep her a secret and protect her reputation.