Promise Me Sunshine

Gather initial thoughts and broad opinions about the book.

1. Did you expect Lenny and Miles to overcome the barriers presented by Lenny’s grief? Were there any points in the novel when you thought they might not end up together?

2. Promise Me Sunshine deals with a lot of sensitive subjects. Did you expect this out of a romance? Why or why not?

3. Did you see the final plot twist of the novel when Lenny reveals that she was the one who wrote the “Live Again” list? What clues in the text led you to expect it?

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

1. Have you ever experienced grief like Lenny does at the beginning of the novel? What or who helped you overcome the worst of it?

2. Is there something that never fails to make you happy, like the way children always make Lenny smile? What does this pattern tell you about yourself? 

3. Have you ever known someone who would “[walk] into hell and [drag you] back out” like Lenny claims Miles does for her (219)?

4. How does the novel depict the relationship between biological family and “found family”? How does this align with your own experience of these concepts?

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

1. What do you think Bastone is trying to say about how we handle grief in modern society? Does she provide any practical solutions for how to treat people who are grieving?

2. What sources of support does Lenny find as she learns to live with her grief? What does her experience suggest about finding community in modern, urban environments?

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

1. How do you think the novel would be different if Lenny had seen Lou’s final note to her at the beginning of the novel? How did the final revelations about the note shift your understanding of Lenny and Lou’s relationship? 

2. How does Lenny change throughout the novel? Are any of the changes she undergoes detectable in how she narrates her story? Do Miles’s changes parallel Lenny’s experiences, or are they entirely different?

3. How does the novel serve as a commentary on the romance genre? How does Bastone employ conventions of the genre, and to what degree does she subvert these conventions? 

4. Bastone makes a point of describing each character’s hair thoroughly. What do you think is the symbolism of hair in the novel?

5. The Staten Island ferry doesn’t let passengers stay on but requires everyone to disembark after each crossing, unlike in the novel. Why does Bastone choose to diverge from reality in this way, and how does this choice affect the symbol and the way Lenny thinks of the ferry in the novel?

Encourage imaginative and creative connections to the book.

1. If you had a Live Again list, what would be on it?

2. If there were a sequel to Promise Me Sunshine, where do you think Miles and Lenny’s relationship would be? How would Miles interact with his family, and how would Lenny be processing her grief?

3. Imagine that you were in Miles’s role. What advice would you give Lenny about grief and how life carries on after loss?