1. How is The Fairest of Them All different from the fairy tales upon which the novel is based? What are some of the similarities?
2. Many fairy tales have omniscient narrators, yet this novel is told from the point of view of Rapunzel. Why do you think the author made the decision to give us Rapunzel’s perspective? How did this influence what you felt about Rapunzel’s choices?
3. Many of us dream about living in a world of princes and princesses, where magic is real and a part of life. What aspects of Rapunzel’s and Snow White’s lives were appealing to you? What are some of the challenges you didn’t expect them to face?
4. Talk about what it’s like to revisit fairy tales you were familiar with when you were younger. What were some of your favorite fairy tales? What other “updated” fairy tales or myths have you read or watched recently?
5. Princes, kings, princesses, and witches are all common characters in fairy tales, and all exist in The Fairest of Them All. How do the characters in this novel compare to the stereotypical princes, kings, princesses, and witches in other fairy tales? When did their actions surprise you?
6. Love of beauty and the complications of aging are important themes in The Fairest of Them All; the king and Rapunzel are particularly obsessed with beauty. Discuss some of the pitfalls of a life lived in luxury and the need for everything to be beautiful.
7. At the end of the novel, Rapunzel thinks of Snow White: “She will be a good queen. One day, she will be a great one.” Why do you think Snow White would make a good queen? What made her father such a bad king?
8. Describe Snow White’s character and the changes she goes through over the course of the story. What did you think of her initial rejection of Rapunzel? How did their relationship evolve?
9. Although Rapunzel and Mathena know a great deal of genuine magic, much of their knowledge is simply an understanding of the earth and of the uses of nature. Why do you think this is associated with witchcraft? Recall some of the magical elements in the novel and their relationship to Mathena (for example: the stag and the magic mirror).
10. Death and rebirth are important themes in the novel. Rapunzel herself says, “. . . out of death comes life. Always.” What do you think this means in the context of the novel? Do you think this is also true of the world in which we live?
11. The conflict between religion and magic is one of the central issues of the story. Why do you think the church is so opposed to witches like Mathena? Why is everyone at the palace suspicious of Rapunzel, when (at least at first) she is helpful and kind?
12. Rapunzel’s magic mirror is what ultimately pushes her to attempt to have Snow White killed. Is the mirror evil and corrupting, or is it only a scapegoat for Rapunzel’s jealousy? Why?
13. Like many fairy tales, The Fairest of Them All is largely about love, true love, lust, and infatuation. Unlike most fairy tales, it is also a story about heartbreak, loss, and violence. What do you think about the book’s take on love and infatuation? How does the novel’s more realistic take on these themes impact the power of the fairy-tale elements?
14. The revelations at the end of the story are foreshadowed early on. Did you catch any of these subtle hints from the stories Mathena told Rapunzel? How did the ending affect the way you viewed the rest of the story? What about how you viewed Mathena?