The Five-Star Weekend

These book club questions are from Bored to Death Book Club.

Book club questions for The Five-Star Weekend by Elin Hilderbrand

Use these discussion questions to guide your next book club meeting.

What does the “Five-Star Weekend” concept mean to Hollis, and how does it evolve throughout the story?

How does the novel explore the complexities of female friendship across different life stages?

Do you think grief is portrayed realistically in Hollis’s journey? How did her coping mechanisms resonate with you?

How does Nantucket as a setting enhance the story? Could this story have worked in a different location?

Forgiveness is a key theme in the book. Which character’s arc of forgiveness impacted you the most?

Which character did you relate to the most, and why?

How do the women’s personal struggles (e.g., Dru-Ann’s career challenges or Brooke’s marriage) add depth to the story?

Hollis is a food blogger. How do her professional and personal lives intertwine in the story?

What did you think of Caroline’s relationship with her mother, Hollis? How did their bond evolve?

Gigi, the “new friend,” brings a fresh perspective. How did she change the group dynamic?

How do Hollis’s friendships reflect the different phases of her life?

Were there any relationships or conflicts you wished had been explored further?

How did the women’s interactions reveal their insecurities or personal growth?

Which friendship in the book felt the most authentic to you?

How do the women reconcile their past mistakes or misunderstandings during the weekend?

What did you think about the pacing of the story? Did it keep you engaged?

Were there any plot twists or reveals that surprised you?

Did you find the ending satisfying? Why or why not?

Elin Hilderbrand often blends light and heavy themes. Did you think the balance worked well here?

If there were a sequel, what would you want to see happen with these characters?

Click here for a printable PDF of the The Five-Star Weekend discussion questions