The Five-Star Weekend

Hollis’s vision of a relaxing, indulgent weekend to battle her grief does not go according to plan. In what ways do the various crises from the weekend help Hollis to grow and move forward? How might a perfect, drama-free, five-star weekend have hindered Hollis’s journey to finding peace?

Cameos of Nantucket locals appear throughout the novel as they admire and gossip about Hollis and the five-star weekend. Why did Hilderbrand include these characters? What perspective do they add?

Compare Caroline’s affair with Isaac to her fling with Dylan. How do these relationships add to the novel’s themes, particularly The Supportive Nature of Friendship?

How do Hollis, Dru-Ann, and Caroline use social media? In what ways does social media work to their advantage? In what ways are they harmed? How do Hollis’s and Dru-Ann’s understanding and use of social media contrast with the ways Caroline and the social media influencers understand and use social media?

In considering what she will miss if she dies from cancer, Tatum realizes Nantucket is one of the greatest loves of her life. Is it possible to love a location as much as a person? Why or why not?

Picture Hollis’s life as if she stayed with Jack and never left Nantucket. Would she be happy? Why or why not?

Dru-Ann, Brooke, and Tatum celebrate growth and happy endings as the weekend concludes. What did Gigi gain from the weekend? Support your answer with evidence from the text.

The younger characters (i.e., Caroline, the social media influencers) learn valuable lessons and make significant changes by the novel’s end. How do the younger women influence the older characters (Hollis, Tatum, Brooke, Dru-Ann, and Gigi)?