47 pages • 1 hour read
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Why is Timmy’s detective agency so important to him? What strengths and weaknesses does he possess as an investigator? What ironies are both hidden and in plain sight regarding Timmy’s skills as a detective?
Discuss the book’s exploration of the power of childhood imagination. How is the importance of childhood imagination represented both through Timmy’s resistance to growing up and through the illustrations in the book? How can his powerful imagination act as a detriment sometimes?
Trace Timmy’s maturation over the course of the book. How do ideas of growing up and changing appear sometimes terrifying or undesirable to him? In what ways does Timmy resist the pressure to grow up, and how does this serve as both a strength and a weakness?
Discuss Timmy’s relationship with Rollo. How does their friendship change over the course of the novel? How does Rollo serve as an example of some of the mature perspectives that Timmy needs to grow into?
Analyze the role of Crispin Flavius in the novel. How is his presence detrimental to Timmy’s development? Does he offer any useful advice? How does Crispin’s presence affect Timmy’s relationship with his mom?
Although Timmy’s performance in school isn’t central to the story he chooses to tell, it does have a potential impact on his life. Trace Timmy’s interactions with his teachers and the school over the course of the novel, considering how things change for him.
Consider Corrina Corrina’s role in the book. Why does Timmy view Corrina Corrina as a nemesis? What, in turn, is Corrina Corrina’s perspective on Timmy? Analyze what lies at the center of Timmy’s animosity for Corrina Corrina.
Trace the change in the tone of the story as the plot progresses and Timmy’s personal life is revealed. What techniques does the author use to shift between humor and more serious moments?
Why does Timmy use his imagination to escape his real life? Identify the stressors in Timmy’s life that cause him to retreat into his own world. Is there a common thread between them?
Discuss the universality of Timmy’s character and experiences. What makes Timmy’s story so relatable, despite all the outlandish events that take place?