The Complete Tales of Winnie-the-Pooh Questions

Bring on the tough stuff - there’s not just one right answer.

  1. Do children really have to grow up and leave the "Hundred Acre Wood?" What would happen if we stayed and did nothing our whole lives?
  2. A lot of people say that childhood today is different than it was back in their day. Which day that was, we're not sure, but they say it anyway.After reading this book, what do you think Milne would say about your childhood? What about your children's?
  3. For a bear with very little brain, Pooh says some profound stuff. Is he really as vacant as the description says he is? What nuggets of wisdom can you find in his silliness?
  4. Friendship is an important theme in Winnie-the-Pooh. Check out the "Themes" section for more on that. But here's a question: are the relationships among the fantastical characters in this book actually realistic? Do they remind you of your friendships?
  5. All children engage in pretend play when they're young. And biologists and psychologists alike tell us that play is an essential way that children learn about the world—from the mechanics of how things work to how to interact in social situations. What do you think Christopher Robin learned during his play with the animals in the Hundred Acre Wood?
  6. The narrative structure of Winnie-the-Pooh is actually pretty complicated. How do you think children respond to the many levels of narrative, the postmodern tidbits, the irony and humor? Do they get it? Do they need to?