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Bring on the tough stuff - there’s not just one right answer.
Why do you think Calvino chose to write If on a winter's night a traveler as a series of first chapters to fictional novels? What point is he trying to make by writing this way?
How do you feel about Calvino's use of second-person narration, where the main character is "you" the Reader? Do you find it involves you more in the book, or is it mostly confusing?
What's the deal with all of the women being sex objects in all ten of the fake novels, as well as the story of "you," the Reader? What kind of picture does this book paint of women and their relation to (apparently male) readers?
Does the book change the way you think about the process of reading? How did you think of reading before encountering this book? How about after?
Why does Calvino lead you, the Reader, all over the world in search of the various novels you've started? What benefit is there to using various cultural styles to write these various first chapters of novels?
By creating endless confusion between authors and book titles, how does Calvino change our perception of authors as individual, flesh-and-blood creators? What is the book's overall approach to authors as the "owners" of the novels they write?
This book constantly speaks of a "void" or "silence" that exists beneath the words of all books. Based on your reading, what can you say about this void? What can anyone say about it? Is it, by definition, something you can't really talk about?
According to Calvino, there seems to be a form of "innocent reading" that is taken away from us by higher education. In what way do scholastic English classes ruin the books we study? How does this question play out in the novel?