Gather initial thoughts and broad opinions about the book.

1. Sexing the Cherry blends historical fiction with surreal fantasy. How did you react to this mix of styles? Did you find the shifts between 17th-century London and fantastical places like a city made of words jarring or engaging?

2. The rewriting of “The 12 Dancing Princesses” fairy tale is a key part of the novel. How did this chapter affect your reading experience? If you’ve encountered other feminist retellings, such as Angela Carter’s stories in The Bloody Chamber (1979), how did Winterson’s approach compare?

3. Which of the two main narrators, the Dog-Woman or Jordan, did you feel more drawn to? What did the contrast between her earthy, pragmatic voice and his philosophical, questing one reveal about the world they inhabit?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. What do you make of Jordan’s quest for the elusive dancer, Fortunata? Thinking about your own life, have you ever pursued something external only to discover it was really about finding a part of yourself? How can external pursuits affect us this way?

2. The Dog-Woman’s immense size is the source of her power, but it also isolates her and makes her feel unlovable. Think about an aspect of your own identity that you consider a great strength. How might that strength also create distance or misunderstanding with others?

3. Jordan’s journey is ignited by his first sight of a banana, a small object that unlocks a universe of possibility for him. Similarly, Nicolas Jordan is inspired by a painting of the first pineapple in England. Has a single object, image, or piece of art ever had a similarly deep effect on you, opening your mind to new ideas or paths?

4. The 20th-century scientist feels a connection to a giant, powerful alter ego as she campaigns against pollution. Do you have a version of yourself you draw on for strength when facing difficult challenges? If you don’t, what might an inner version of you look like?

5. Nicolas Jordan feels disconnected from his modern world and turns to historical books and artifacts to find a sense of heroism and purpose. What stories, historical periods, or art forms do you turn to for inspiration or a sense of connection to something larger than yourself?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. What does the novel suggest about religious hypocrisy through the characters of Preacher Scroggs and Neighbour Firebrace? Where do you see similar dynamics of public piety clashing with private behavior in society today or in other works you’ve encountered?

2. How does the 1990s scientist’s lonely protest against corporate pollution speak to contemporary environmental movements? What does her struggle say about the challenges and personal costs of fighting against powerful systems?

3. The story is set against the backdrop of the English Civil War, a time of ideological division between Royalists and Puritans. In what ways does this historical conflict over morality, pleasure, and governance mirror the cultural or political divides we face in the modern world?

Dive into the book’s structure, characters, themes, and symbolism.

1. The novel argues that time is not a straight line but a simultaneous reality where past and present coexist. How does Winterson use the narrative structure to make this philosophical argument feel real to you as a reader?

2. How does the recurring motif of weight and lightness explore different forms of feminine power? How do these elements in the text reflect real-world concerns regarding social judgments of women’s bodies?

3. The theme of Reclaiming Agency Through Storytelling is a critical part of understanding Winterson’s characters. The Dog-Woman is the type of character who would normally be voiceless in history, yet she commands half the narrative. How does her first-person account empower her and challenge traditional historical records?

4. How does the motif of journeys and maps explore the difference between external reality and internal truth? How does the novel work both to persuade the reader that all of the events, or none of the events, are real?

5. For those who have read other works by Jeanette Winterson, like Oranges Are Not the Only Fruit (1985), how does this novel’s exploration of identity, history, and unconventional love compare? What elements feel uniquely “Winterson” to you?

Encourage imaginative and creative connections to the book.

1. The novel is filled with fantastical places, like the city where words form a physical cloud in the sky. If you were to add another such city to Jordan’s travels, what unique rule or quality would define it, and what would it reveal about its inhabitants?

2. Imagine you are John Tradescant curating an exhibit for “The Ark,” his collection of rarities. Which single object from the story would you choose to represent the Dog-Woman, and what would the museum label say about her?

3. If you were to set a modern-day version of this story, who would be the contemporary equivalents of the Dog-Woman and Jordan? What social or political issues might they find themselves fighting for or against?

4. Research a historical figure with whom you feel a connection. How would you handle situations they faced in their own time? How do you think they would handle a problem or struggle in your life?