Chapter 1 introduces nine-year-old Iggy Frangi, whom the narrator describes as the hero of this book. However, being a hero doesn’t mean Iggy is “polite and nice and plays the cello and reads for at least half an hour before bedtime” (9). Instead, Iggy is mischievous and often does things he later regrets.

The narrator says there are three kinds of regret: things people wish they hadn’t done only because they got caught, things people wish they hadn’t done quite as much of, and things people truly regret doing altogether. Iggy experiences all three kinds of regret in this story. At the moment, Iggy is bored, lying face down on a rug, in timeout in his room because of something he did. Page 11 illustrates Iggy standing between his shouting parents. Iggy has no TV or computer since his parents believe in raising screen-free kids. As a consequence of his actions, Iggy has to stay in his room until dinnertime, can’t have dessert for a week, loses his allowance for a month, and must write an apology letter. Despite these punishments, Iggy is laughing.