1. Why does the book only include Leigh Botts's letters, without any responses from Mr. Henshaw?

2. How does Mr. Henshaw feel about children who write him letters, and what are his feelings toward Leigh specifically?

3. In what way is the setting of Dear Mr. Henshaw significant to the narrative?

4. Why does Angela Badger appreciate A Day on Dad's Rig even though it's merely a description rather than a full story?

5. After going to such lengths to identify the lunch bag thief, why does Leigh ultimately not want to discover who it is?

6. By the conclusion of the book, would Leigh still consider himself "the mediumest boy in the class"?

7. What do the monarch butterflies represent in the story?

8. What elements are missing from Leigh's tale about the ten-foot-tall wax truck driver, and who might the wax man symbolize?

9. Why is Leigh initially unable to complete his thank-you note to his father for the twenty dollars, and what allows him to eventually write it?

10. Leigh deeply misses his dog Bandit and is heartbroken when his father loses him. So why does he return Bandit to his father after the dog is found?

11. Does the author reveal any flaws in the characters of Leigh's mother and father?