The Summer We Started Over Book Club Kit

Discussion Questions

  1. The Summer We Started Over explores many poignant themes, including grief, self-discovery, embracing change, and taking chances on love and personal fulfillment. Which theme and storyline resonated the most deeply with you, and why?
  2. Examine the role of the setting, both the summer season and the location of Nantucket, in the novel. How does the season of change parallel the characters’ personal growth and transformation? How does the island’s dynamic as a popular tourist destination play a role in the story?
  3. Discuss the different paths to happiness pursued by Eddie, Barrett, and Bill. How do their individual journeys reflect their personalities and values?
  4. Analyze the theme of pursuing dreams. How do Eddie and Barrett’s aspirations compare and contrast, and what obstacles do they face in achieving their goals?
  5. How does the theme of grief play out in the story? How do the losses that Eddie, Barrett, and Bill have experienced shape their individual journeys?
  6. Explore Eddie’s struggle to find her place both professionally, romantically, and in regard to motherhood. How does her uncertainty about her career path, her desires for a fulfilling romantic relationship, and her hesitancy towards motherhood influence her personal growth and overall pursuit of happiness?
  7. Analyze Barrett’s character and motivations. What drives her passion for opening Nantucket Blues, and how does this dream shape her identity? How does her pursuit of her dream impact her relationships and personal fulfillment?
  8. Discuss the role Dinah plays in the lives of Eddie, Barrett, and Bill during The Summer We Started Over, and the ways that each of them—and Nantucket!—impact her in return.
  9. How does Dove’s return, death, and the introduction of her young son Bobby impact each of the family members?
  10. Reflect on the overall message of the novel. What lessons can be gleaned from the characters’ experiences about finding happiness and following one’s dreams?