Book Club Questions for That Summer by Jennifer Weiner

by Heather Caliendo
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Book club questions for That Summer by Jennifer Weiner takes a closer look at this complex novel. There will be spoilers so for more context about the book, check out my review first.

Whew. I had a lot of thoughts about this one, which I covered in the review. I do believe the marketing was very misleading—this was not some light summer read. There should be trigger warnings so the reader knows exactly what the story is about. I don’t like that the publisher danced around the subject.

Definitely let me know if you had expected more of a beach read rather than a story that covers the #metoo movement. That’s not to say I didn’t feel the story was impactful and handled with care but again, the marketing really failed with this one.

Let me know your thoughts about this!

The Synopsis

Daisy Shoemaker can’t sleep. With a thriving cooking business, full schedule of volunteer work, and a beautiful home in the Philadelphia suburbs, she should be content. But her teenage daughter can be a handful, her husband can be distant, her work can feel trivial, and she has lots of acquaintances, but no real friends. Still, Daisy knows she’s got it good. So why is she up all night?

While Daisy tries to identify the root of her dissatisfaction, she’s also receiving misdirected emails meant for a woman named Diana Starling, whose email address is just one punctuation mark away from her own. While Daisy’s driving carpools, Diana is chairing meetings. While Daisy’s making dinner, Diana’s making plans to reorganize corporations. Diana’s glamorous, sophisticated, single-lady life is miles away from Daisy’s simpler existence. When an apology leads to an invitation, the two women meet and become friends. But, as they get closer, we learn that their connection was not completely accidental. Who IS this other woman, and what does she want with Daisy?

From the manicured Main Line of Philadelphia to the wild landscape of the Outer Cape, written with Jennifer Weiner’s signature wit and sharp observations, That Summer is a story about surviving our pasts, confronting our futures, and the sustaining bonds of friendship.

Book Club Questions for That Summer

  1. The above synopsis hints that there’s more going on in this story than just a case of mistaken identity over email but it doesn’t give much more than that. Did you expect That Summer to be more of a lighter book?
  2. This one is positioned as a beach read—what’s your opinion of a good beach read type story?
  3. Do you feel the focus on the #metoo movement in this novel was handled in an impactful way?
  4. We meet Daisy when she’s at a bit of a standstill. Her cooking business is doing ok (maybe not so thriving like the synopsis says), she’s having trouble connecting with her eccentric teenager daughter (Beatrice) and her husband Hal is more aloof than not. Have you ever had a time in your life where you feel like you’re stuck in a rut?
  5. If you got seemingly mistaken emails like Daisy did, how would you have handled it?
  6. Why was Daisy so eager to meet Diana?
  7. The two start an unlikely friendship—despite the fact that Diana is completely lying to Daisy about her true intentions. What did you make of this friendship?
  8. In the prologue, we meet teenage Diana as she’s excited to go to a party with the older boy she has a crush on. We eventually find out that she was raped by this boy at the party and it turns out to be Hal. What did you think when you realized that boy was the adult Hal?
  9. The real-life #metoo movement makes its way to the book with references to Harvey Weinstein, Matt Lauer, etc. The coverage of the #metoo movement inspired Diana to confront Hal, Danny and Brad. Let’s talk about Diana’s need to confront these men in order to get some type of closure and hold them accountable.
  10. She first meets with Brad where he admits his part in the assault was wrong. He then commits suicide and Diana blames herself. What are your thoughts on this?
  11. Daisy’s real name is Diana but Hal asks her to go by Daisy. At the time, Daisy thinks it’s just a cute, romantic gesture. But we know it’s because Hal is fully aware of what he did to Diana. Do you believe Daisy was pretty naive about all things Hal? Why didn’t she question his actions more?
  12. Eventually everything comes to the head and Daisy learns the truth about Hal and her brother Danny. First, will she ever forgive Danny?
  13. Why do you think Jennifer Weiner included that chapter with Hal’s perspective?
  14. The epilogue leaves plenty of questions unanswered—mainly between Hal and Daisy. Will Daisy divorce him? What did you think about the fact that Hal didn’t seem to face much consequences for his horrible act?

More Recommendations

Hope you enjoyed book club questions for That Summer! Here are some more recommendations and links to book club questions.

Mrs. Everything by Jennifer Weiner

Mrs. Everything by Jennifer Weiner is another impactful novel. It’s more of a literary style than straight up women’s fiction.

Jo and Bethie Kaufman were born into a world full of promise.

Growing up in 1950s Detroit, they live in a perfect “Dick and Jane” house, where their roles in the family are clearly defined. Jo is the tomboy, the bookish rebel with a passion to make the world more fair; Bethie is the pretty, feminine good girl, a would-be star who enjoys the power her beauty confers and dreams of a traditional life.

But the truth ends up looking different from what the girls imagined. Jo and Bethie survive traumas and tragedies. As their lives unfold against the background of free love and Vietnam, Woodstock and women’s lib, Bethie becomes an adventure-loving wild child who dives headlong into the counterculture and is up for anything (except settling down). Meanwhile, Jo becomes a proper young mother in Connecticut, a witness to the changing world instead of a participant. Neither woman inhabits the world she dreams of, nor has a life that feels authentic or brings her joy. Is it too late for the women to finally stake a claim on happily ever after?

In “her most sprawling and intensely personal novel to date” (Entertainment Weekly), Jennifer Weiner tells a “simply unputdownable” (Good Housekeeping) story of two sisters who, with their different dreams and different paths, offer answers to the question: How should a woman be in the world?

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


The Last Thing He Told Me by Laura Dave

Ooo I really enjoyed The Last Thing He Told Me by Laura Dave! A very intriguing read.

Before Owen Michaels disappears, he smuggles a note to his beloved wife of one year: Protect her. Despite her confusion and fear, Hannah Hall knows exactly to whom the note refers—Owen’s sixteen-year-old daughter, Bailey. Bailey, who lost her mother tragically as a child. Bailey, who wants absolutely nothing to do with her new stepmother.

As Hannah’s increasingly desperate calls to Owen go unanswered, as the FBI arrests Owen’s boss, as a US marshal and federal agents arrive at her Sausalito home unannounced, Hannah quickly realizes her husband isn’t who he said he was. And that Bailey just may hold the key to figuring out Owen’s true identity—and why he really disappeared.

Hannah and Bailey set out to discover the truth. But as they start putting together the pieces of Owen’s past, they soon realize they’re also building a new future—one neither of them could have anticipated.

With its breakneck pacing, dizzying plot twists, and evocative family drama, The Last Thing He Told Me is a riveting mystery, certain to shock you with its final, heartbreaking turn.

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

Happy reading!

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