The novel follows the correspondence between students from two rival schools. Cassie Aganovic, Emily Thompson and Lydia Jaackson-Oberman, attend the prestigious, private Ashbury High; Matthew Dunlop, Charlie Taylor, and Sebastian Mantegna ("Seb") attend the public and notoriously rough, Brookfield High. In a special pen-pal program between the schools (previously seen in "Feeling Sorry for Celia" and set up by Mr. Botherit), Cassie begins to write to Matthew; Emily writes to Charlie; and Lydia exchanges letters with Seb. The letters are initially different degrees of hostile. Emily and Charlie poke fun at each other's writing, while Lydia and Seb bicker about whether or not they can trust each other. Matthew however, is much worse. He continuously threatens Cassie (i.e. "I'll break your fingers one by one"), but she responds calmly and tells no one of the abusive letters. Over time, the letters change tones. Charlie and Emily go on "practice dates" to help Charlie date the girl of his dreams, Christina Kratovac (who was the Brookfielder Elizabeth Clarry wrote to in "Feeling Sorry For Celia"). Lydia and Seb participate in "Secret Assignments" that eventually lead to their forming a close relationship. Cassie and Matthew begin to go down a similar path and plan a meeting after Cassie finally starts getting civil responses from Matthew. However, his sudden kindness is a ploy. He stands her up and then, on a following meeting, proceeds to rip up a letter that she had sent and openly mock her. This is especially hard for Cassie, because her father had recently died of cancer and Cassie had not yet come to terms with his death. This is why she never reported Matthew's initial abusive letters, she had not been feeling like herself and had lost her confidence.