Printable: Book Club Questions for 28 Summers by Elin Hilderbrand

Both the synopsis and the first chapter “spoil” the story with the fact that Mallory is dying. And that her and Jake never truly got together (other than the one-weekend-per-year affair). What do you think about the story choice to give away the ending and be upfront that Mallory will pass away? Did that impact how you read the story?
What were your initial thoughts about the dynamic between Mallory and Jake? Why did they decide to meet once a year in Nantucket?
Why do you think Mallory and Jake never tried to be together? Do you think their relationship would have worked out if they gave it a try?
Jake has been with Ursula for a long time. And he feels connected to Ursula due to her close friendship with his sister who passed away young. What did you think about their relationship? Did it make sense to you or was it perplexing? Why do you think Jake couldn’t bring himself to break up with Ursula for Mallory?
Mallory is in love with Jake and because of that, every relationship she tries always ends in her breaking it off before the weekend with Jake. What did you think about Mallory’s decision making? Did you wish she would have broke up with Jake?
We follow Ursula’s career trajectory pretty closely. Were you engaged with her storyline or did you not really care for her? Did she truly love Jake? What did you think about the addition of all the politics?
Each section starts off with what everyone was talking about that year. Did you like that addition?
Let’s talk about Leland’s Letter where she wrote about Mallory and Jake’s relationship. What did you think about Mallory and Leland’s friendship overall?
Mallory and Fray hook up at Cooper’s wedding and she ends up getting pregnant with Link. What did you think about that?
When Ursula decides to run for president, she comes to Nantucket and asks (pretty much demands) Mallory to stop seeing Jake. What did you think about this scene? Why did Mallory eventually agree to stop seeing him?
What did you think about the ending? Was it enough closure for you? Why or why not?
Do you think that Link and Jake’s daughter Bess will get together?