Gather initial thoughts and broad opinions about the book.

1. Was this your first experience with K. L. Walther’s novels? If you’ve read The Summer of Broken Rules, how did it compare to The Summer of Second Chances?

2. How effectively did you think the novel balanced its romance and humor with heavier topics like the challenges of dementia and conflict within blended families?

3. Did you find Olivia’s journey relatable? How did her responses to her circumstances resonate with you?

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

1. Olivia’s project to recreate her grandmother’s photos is her way of holding onto memories in the face of loss. Are there meaningful traditions or rituals in your own life or family? How do they help you connect with your past or with the people you care about?

2. Erica points out that Olivia tends to choose people she can leave before they can hurt her. Has there been a time in your life when you put up an emotional wall to protect yourself? What did you learn from that?

3. The novel ends with a second chance at romance—a traditional romance trope. Have you ever wished you could get a “do-over” in a conversation or a relationship, and what do you think makes that idea so appealing?

4. Olivia feels like an outsider in her blended family, interpreting things like the gift of a luggage set as a sign she doesn’t belong. Have you ever felt particularly included or excluded in a group or community? What made you feel that way?

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

1. Annie’s engagement to Christian ended because his family disapproved of her social standing. What does their story suggest about the role of class in relationships? In what ways do you think these kinds of societal pressures have changed or remained the same in our contemporary world?

2. Caring for Annie takes an emotional and physical toll on Olivia. What does her experience reveal about the expectations that society places on young people, particularly young women, to take on this kind of responsibility?

3. The relationship between Olivia and her stepmother, Erica, transforms across the novel. How does their journey compare to the way blended families are often portrayed in movies or on television? In what ways does their story reinforce or subvert common stereotypes?

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

1. The story of Annie and Christian’s past romance runs parallel to Olivia and Connor’s developing love. How does learning about her grandmother’s lost love influence Olivia’s choices in her own relationship?

2. Connor’s emotional openness works as a foil to Olivia’s guardedness. How does this difference in personality change the direction of their relationship?

3. Walther anchors each plot turn to a named landmark, such as Jaws Bridge, the Flying Horses Carousel, and other real Martha’s Vineyard sites. Do these specific, tangible places deepen the sense that the island itself holds secrets?

4. What scene or conversation acts as a turning point in Erica and Olivia’s relationship?

5. Annie’s Polaroids and watercolors set Olivia’s entire journey in motion. How do those objects influence her choices across the novel?

Encourage imaginative and creative connections to the book.

1. The book ends just as Olivia and Connor begin their “second chance” at romance. Write an extra scene describing their date.

2. If you were to create a memory book for a loved one, following Olivia’s example, what three “landmarks” from your shared history would you choose to revisit and photograph? What makes those particular places so significant?

3. Imagine you’re the music supervisor for a film adaptation of The Summer of Second Chances. What song would you choose for the scene where Olivia and Connor take their first leap off Jaws Bridge? What makes that song a perfect fit for the moment?