Summer of '69

Content Warning: This section of the guide contains discussion of substance use, addiction, and racism.

Gather initial thoughts and broad opinions about the book.

1. How effectively does Hilderbrand weave historical events like the Vietnam War, moon landing, and the Chappaquiddick incident into the personal dramas of the Foley-Levin family? How does her approach compare to other novels set in the same period, such as Kristin Hannah’s The Women?

2. Hilderbrand revisits these characters in Summer of ’79. What aspects of the 1969 summer make you want to continue following this family’s story?

3. What struck you most about how each family member handles crisis differently throughout this pivotal summer?

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

1. Kate’s alcohol misuse and secret-keeping deeply affect her relationships with her family. How do family secrets in your own experience shape family dynamics?

2. Jessie’s shoplifting serves as a way for her to feel in control when everything else feels chaotic. What coping mechanisms have you seen people use when feeling powerless?

3. Each sister—Blair, Kirby, and Jessie—faces different challenges with male figures in their lives. Which sister’s journey resonated most with your own experiences or observations?

4. The novel shows how historical events like the Vietnam War create anxiety that permeates family life. How do current events affect the emotional climate in your family?

5. Exalta’s transformation as a result of her relationship with Bill suggests people can change at any age. What examples have you witnessed of people growing and changing later in life?

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

1. Kirby and Darren’s interracial relationship faces family resistance and social challenges. How does their experience reflect the complexities of racism in 1969 America?

2. The different male characters in the novel reflect changing expectations of masculinity in the late 1960s. How do figures like Garrison, Scottie, Angus, and David represent different approaches to male behavior and power?

3. Blair’s struggle between career ambitions and traditional wife/mother roles reflects women’s changing opportunities. How do her challenges compare to those faced by women in a contemporary context?

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

1. Hilderbrand uses alternating points of view to tell the story. How does switching between Kate, Blair, Kirby, and Jessie’s perspectives enhance your understanding of the family dynamics?

2. The chapter titles draw from popular 1960s songs like “Fortunate Son” and “Both Sides Now.” How do these musical references enhance the novel’s themes and atmosphere?

3. Jewelry pieces appear repeatedly as symbolic objects throughout the novel. What do Tiger’s grandfather’s ring, Jessie’s two necklaces, and Blair’s silver lighter reveal about family legacy and individual identity?

4. The moon landing occurs simultaneously with Blair giving birth to her twins. How does this historical moment symbolize the changes happening within the Foley-Levin family?

5. Kate’s journey from secretive alcoholic to honest matriarch drives much of the novel’s emotional arc. What specific moments mark her transformation throughout the summer?

6. Why does the summer of 1969 serve as the perfect setting for these characters’ stories of growth and change? Why might Hilderbrand have chosen this specific period for her story?

Encourage imaginative and creative connections to the book.

1. Write a family newsletter for the Foley-Levins to keep in touch while scattered across different locations. What sections would you include and what family news would each character contribute?

2. Imagine you’re creating a time capsule with Jessie to bury at All’s Fair that captures the essence of the summer of 1969. What five items would you choose to represent the major events and changes of that season?

3. The novel ends at Thanksgiving of 1969 with the family gathered together. Write an epilogue showing the family five years later in 1974. What do you think would have changed and what would have stayed the same?