1. While Milo is the protagonist of the story, is he an extraordinary character? How representative is he of children today?

2. The Mathemagician argues that numbers hold more significance than words, whereas King Azaz believes the opposite. Do you think one is more crucial than the other, or do you side with Rhyme and Reason, who say they are equally important?

3. The Humbug is described as a liar and a fraud, and the Spelling Bee calls him "a very dislikable fellow." Why is he referred to as "lovable" at the book's conclusion? What changes our perception of him?

4. What lessons does Milo gain from leading Chroma's orchestra? How does he feel once the experience concludes?

5. Milo's parents are never mentioned in the story. Why do you think Juster chose to exclude them?

6. The book features several demons, including the Terrible Trivium, the demon of meaningless tasks; the demon of insincerity; the Gelatinous Giant; the Overbearing Know-it-All; and the Threadbare Excuse. What are some other demons that could be named after bad habits?

7. At the end of Milo's adventure in the lands beyond, why does the tollbooth vanish? Why doesn't it stay so he can revisit the Kingdom of Wisdom repeatedly?

8. How would you react if a tollbooth appeared in your room? Given your knowledge of the Kingdom of Wisdom, would you want to visit? How do you think your reactions to the situations Milo encountered would differ from his?