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That Summer Book Club Questions

With such a complex and layered story, there are a lot of discussion options for That Summer book club questions.

Picking up what I thought was a New York Times recommended light-hearted beach read, I was definitely surprised once I actually started the book.

While it is well written and cleverly laid out, this novel is actually a “real” world tale of how the #metoo movement caused old stories to surface.

Once I got over the fact the book was wildly different than what I was expecting, I really enjoyed it. 

That Summer Book Club Questions

Another Timely Novel from Jennifer Weiner

Written by the author of Big Summer, Jennifer Weiner, this novel tells the story of two Dianas linked together through fate and history.

Our main characters Diana Starling and Diana/ Daisy Shoemaker become acquainted for the first time over a cute mix-up over an email address. The two women meet and stories are exchanged.

Daisy shares how despite having a lot of the trappings of success (a handsome husband, a beautiful home, a thriving cooking business, and a spirited teenage daughter), she may not be totally happy.

Diana doesn’t share how she orchestrated the whole meeting because of who Daisy’s husband is.

woman staring out the window for That Summer Book Club Questions
Source: Unsplash

The novel is full of plot twists and complex questions that deserve to be thought through.

Whether you are looking for more additions to your summer book club, or just want to drill into some of the more intense themes on your own, these That Summer book club discussion questions will help you focus on the most interesting points.

Enjoy this reading group guide!

That Summer Book Club Questions

1. That Summer contains an epic prologue detailing everything that happens to Diana the summer she works as a Mother’s Helper in Cape Cod, right up until the moment she has a drink at the “end of summer” bonfire. 

Just from this beginning, what did you get the sense the rest of the book would be about? How close were your expectations to reality? 

end of summer bonfire from That Summer
Source: Unsplash

2. This is the second book by Jennifer Weiner that some readers have found to be very different than what it was positioned as with its marketing.

Another of her works, Big Summer, seems like a body-positive story until it turns into a who-dun-it murder mystery.

Did you start the book thinking it was a light-hearted story? Did that color your impressions or enjoyment of the book at all?

3. If you had mistakenly been getting emails from someone else with the same name as you, would you have handled things the same way Daisy did? What might you have done differently?



4. When the two Dianas finally meet, “Daisy” tells her new acquaintance a lot of details about her life. What do you think made Daisy open up so quickly to a stranger?

5. Daisy calls making a friend as a woman in her middle age the closest thing they have to falling in love. Do you agree with that idea? 

Do you think it’s actually harder to make friends as an adult? Why?

Wine cheers That Summer Book Club Questions
Source Unsplash

6. A lot is made of out the fact Daisy leaves school to marry Hal at a very young age. Do you think attitudes towards marriage have changed much over the years? 

Daisy says she was looking for love and security. Is that still the main reason you hear for marriage these days?

7. Diana starts to really like Daisy and almost tells her about her assault before she is interrupted by a phone call. 

Do you think the story might have unfolded differently if Diana had been able to confide in Daisy at that moment?

8. When everything comes out, Daisy realizes her brother Daniel knew about Hal’s past and let her marry him anyways. Even her mother knew about Hal’s past.

How did you react when you found out these additional facts about Daisy’s family? Did any of the excuses they gave her hold up for you?

9. During the whole book, Michael has been a source of support and comfort to Diana, encouraging her to find closure if she can. Do you think his encouragement ultimately helped or hurt her?

10. This book mentions real-life cases that came about during the #metoo movement. 

Did anything about how Jennifer Weiner presents them make you think more closely about those real-life events?

Diana is a fictional character, but how do you think they must have impacted other victims like Diana?

Man on trial That Summer Book Club Questions
Source: Unsplash

11. The end of the book presents two possible realities. An imaginary one where Hal slips and dies on the deck, and the one where Daisy asks for a divorce. 

Are you satisfied with the ending that is the “real” one? Was justice is served for Diana and Daisy?

12. The book presents different viewpoints from the various characters. Is there anyone in the book you think is deserving of a second chance? Why or why not?

13. After finishing the book, how was your overall mood? Did the book stick with you, or were you able to move on from it fairly quickly?

14. What ultimately surprised you the most about the book? What felt the most formulaic?

15. Did That Summer make you want to look up more books by Jennifer Weiner? What or why not?

Get a copy of these book club questions as a PDF below.


Don’t have a book club yet? Why not start your own! Check out my article on How to Form a Book Club for tips on creating the ideal club for your lifestyle.


Did you read That Summer by Jennifer Weiner for your book club? What did you think?

Leave me a comment below about how the questions and book worked for you!