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Book Club Questions for 28 Summers by Elin Hilderbrand

Book Club Questions for 28 Summers by Elin Hilderbrand

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Book club questions for 28 Summers by Elin Hilderbrand takes a closer look at this bittersweet novel. For more context about the story, check out my spoiler-free review

This was my first Elin Hilderbrand book. I loved the setting and enjoyed her writing. But as I mentioned in my review, I did have some issues with the storyline. There’s a ton going on in this one and I didn’t always buy the reasons why Jake and Mallory couldn’t be together. I’m very curious to hear what you all thought of this! I will say, there’s a ton to unpack in this story. 

That said, the Nantucket storyline = amazing!! One of my favorite settings I’ve read in a long time. Even though I didn’t love this one, I will read her stories in the future for the setting alone. 


When Mallory Blessing’s son, Link, receives deathbed instructions from his mother to call a number on a slip of paper in her desk drawer, he’s not sure what to expect. But he certainly does not expect Jake McCloud to answer. It’s the late spring of 2020 and Jake’s wife, Ursula DeGournsey, is the frontrunner in the upcoming Presidential election.

There must be a mistake, Link thinks. How do Mallory and Jake know each other?

Flash back to the sweet summer of 1993: Mallory has just inherited a beachfront cottage on Nantucket from her aunt, and she agrees to host her brother’s bachelor party. Cooper’s friend from college, Jake McCloud, attends, and Jake and Mallory form a bond that will persevere — through marriage, children, and Ursula’s stratospheric political rise — until Mallory learns she’s dying.

Based on the classic film Same Time Next Year (which Mallory and Jake watch every summer), 28 Summers explores the agony and romance of a one-weekend-per-year affair and the dramatic ways this relationship complicates and enriches their lives, and the lives of the people they love.

Book Club Questions for 28 Summers

  • 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?

More recommendations 

Hope you enjoyed book club questions for 28 Summers! Here are some more recommendations along with links to book club questions. 

Big Summer by Jennifer Weiner 

Big Summer by Jennifer Weiner is such an entertaining story!

Six years after the fight that ended their friendship, Daphne Berg is shocked when Drue Cavanaugh walks back into her life, looking as lovely and successful as ever, with a massive favor to ask. Daphne hasn’t spoken one word to Drue in all this time—she doesn’t even hate-follow her ex-best friend on social media—so when Drue asks if she will be her maid-of-honor at the society wedding of the summer, Daphne is rightfully speechless.

Drue was always the one who had everything—except the ability to hold onto friends. Meanwhile, Daphne’s no longer the same self-effacing sidekick she was back in high school. She’s built a life that she loves, including a growing career as a plus-size Instagram influencer. Letting glamorous, seductive Drue back into her life is risky, but it comes with an invitation to spend a weekend in a waterfront Cape Cod mansion. When Drue begs and pleads and dangles the prospect of cute single guys, Daphne finds herself powerless as ever to resist her friend’s siren song.

A sparkling novel about the complexities of female relationships, the pitfalls of living out loud and online, and the resilience of the human heart, Big Summer is a witty, moving story about family, friendship, and figuring out what matters most.

You can order the book on Amazon here. Check out my book club questions here

Beach Read by Emily Henry

Beach Read by Emily Henry is another perfect one to read this summer!

Augustus Everett is an acclaimed author of literary fiction. January Andrews writes bestselling romance. When she pens a happily ever after, he kills off his entire cast.

They’re polar opposites.

In fact, the only thing they have in common is that for the next three months, they’re living in neighboring beach houses, broke, and bogged down with writer’s block.

Until, one hazy evening, one thing leads to another and they strike a deal designed to force them out of their creative ruts: Augustus will spend the summer writing something happy, and January will pen the next Great American Novel. She’ll take him on field trips worthy of any rom-com montage, and he’ll take her to interview surviving members of a backwoods death cult (obviously). Everyone will finish a book and no one will fall in love. Really.

You can order the book on Amazon here. Check out my book club questions here