Bring on the tough stuff - there’s not just one right answer.
- Why is the book made up of letters and journal entries? Why aren't there any "regular" chapters? How does this affect the way we read the book?
- Why does it end the way it does? Why doesn't the family reunite?
- Leigh writes just as much (or maybe even more) in his diary as he does to Mr. Henshaw. Why isn't the book titled Dear Diary?
- The Newbery Medal is given "to the author of the most distinguished contribution to American literature for children." Why do you think Cleary got the medal for this story?
- There's a lot of sadness and disappointment in this book. Why did the author write a book for kids that's so depressing at times?
- What do you think the author believes about what it means to be a mature type of kid?
- How did you imagine Mr. Henshaw to be? Would you have liked the book better if he had made an appearance?