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

1. Which part of the novel evoked a strong emotional response from you? What about that scene or situation made you have a strong reaction?

2. How does the novel’s theme of The Role Serendipity Plays in Love relate to your own life? Do you believe that people can have as strong a connection as Daniel and Six do so soon after meeting, and do you think that the novella depicts a realistic relationship? Why or why not?

3. How do you think you would respond in Six’s situation after she discovered her pregnancy while abroad in Italy? Do you think her decision was understandable and/or realistic?

4. This novel was originally published in 2013. How do you think our world has changed from the time in which the novel was published? Are there any aspects of the novel’s attitudes or themes that you think would be received differently by a contemporary audience?

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

1. What are the novella’s attitudes toward sex and intimacy? Explore how Six’s supposed “promiscuity” is framed within the text and what her perception of and feelings about her number of sexual partners say about what society communicates to young girls about sex and their sexuality.

2. The “Cinderella” fairy tale is a direct inspiration for Finding Cinderella. How does this modern retelling connect to and deviate from the original, and how does it relate to other modern-day “Cinderella” retellings?

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

1. How does the novella’s structure impact the story? Specifically, how does the use of a flashback to the maintenance closet at the end of junior year and then the jump forward in time function within the text?

2. Which character do you think develops or changes the most throughout the story? What evidence in the text illustrates this growth and change?

3. What does Daniel learn through his relationships with Val, Holder, and Six? How does his understanding of unconditional love take shape throughout the text?

4. One significant theme in the novella is the importance of Honesty and Vulnerability in Building Connections. How does this theme appear within the context of Six and Daniel’s relationship throughout the text?

5. What does the maintenance closet symbolize, and how does this symbol function throughout the course of the text? How does it function differently in the beginning of the text versus the end?

6. Discuss how the motif of fairy tales shapes your understanding of the text.