Pineapple Street
by Jenny Jackson
Discussion Questions:
1. The Stockton family is both a typical and extremely unusual American family. Are there ways in which you relate to them, and others in which find them entirely unrelatable?

2. The novel is set in the small neighborhood of Brooklyn Heights, offering historical, architectural, and cultural details about the community. How does the setting shape the characters in this novel?

3. How would you characterize each sibling's relationship with the generational wealth they were born into? Georgiana is the baby of the family, ten years younger than her siblings. Does Georgiana's age alter her attitudes about wealth?

4. Brady claims to be in love with Georgiana. Do you believe him? Do you think his treatment of Georgiana was despicable, or were his intentions good?

5. Georgiana has two very different love interests, Brady and Curtis. Compare and contrast the two men. What does she get from each of them?

6. Darley left the workforce to raise her two children but feels deeply conflicted about her identity as a stay-at-home mom. Why does Darley's background make this especially fraught for her? How does she have it easier than other parents?

7. Darley keeps Malcolm's firing a secret from the Stocktons. Is this an act of love, or a betrayal of Malcolm-or both? Is Darley a good ally?

8. In the opening chapter, Sasha is mistaken for a server at the housewarming party, which makes her feel further out of place among her in-laws and their guests. At what other points in the novel is it made clear that Sasha is an outsider? Do you think Sasha will eventually gain an intuitive understanding of how the Stocktons dress and act? Could you change your instincts in a circumstance like that?

9. Sasha finally asks Cord to put her first, to put her needs before those of his family. Is she holding him accountable enough? Do you think Cord has been fair to Sasha?

10. What does Mullin represent for Sasha? What did she learn from that relationship? How did Mullin set her up to look for the wrong things in a marriage?

11. What does the house on Pineapple Street represent for the characters in this book? Does it have a different meaning to each of them?

12. Darley says she is an orange, Cord is a pineapple, and Georgiana is a cranberry. Which fruit would you characterize Sasha as? Which fruit would you be?

Discussion Questions by the publisher

Book Club Talking Points:
A book about old money and class, the rules of being very wealthy, and the problems of "fitting in" if you are not born into old money. It also explores the concepts of change and facing challenges - which are universal.


PbrHome - totes, wine bags, pillows for the book lover
Go There Now
More Reading Suggestions
Popular Books
If you have a passion for reading and, like most, have no time to find the right book, browse the most popular books trending right now. They are all page-turners, and they all let you escape from reality.

Popular Book-  The Song of Achilles by Madeline Miller
The Song of Achilles
By Madeline Miller
A tale of gods, kings, immortal fame, and the human heart, THE SONG OF ACHILLES is a dazzling literary feat that brilliantly reimagines Homer's enduring masterwork, The Iliad. An action-packed adventure, an epic love story, a marvelously...More


Popular Book-The Seven Husbands of Evelyn Hugo by Taylor Jenkins Reid
The Seven Husbands of Evelyn Hugo
by Taylor Jenkins Reid
In this entrancing novel "that speaks to the Marilyn Monroe and Elizabeth Taylor in us all" (Kirkus Reviews), a legendary film actress reflects on her relentless rise to the top and the risks she took, the...More


Popular The Silent Patient by Alex Michaelides
The Silent Patient
by Alex Michaelides
The Silent Patient is a shocking psychological thriller of a woman's act of violence against her husband-and of the therapist obsessed with uncovering her motive. Alicia Berenson's life is seemingly perfect. A famous painter...More


Popular Book- Where the Crawdads Sing by Delia Owens
Circe
By Madeline Miller
In the house of Helios, god of the sun and mightiest of the Titans, a daughter is born. But Circe is a strange child-not powerful, like her father, nor viciously alluring like her mother. Turning to the world of mortals for ...More


Popular Book- The Unhoneymooners by Christina Lauren
The Unhoneymooners
By Christina Lauren
AFor two sworn enemies, anything can happen during the Hawaiian trip of a lifetime-maybe even love-in this romantic comedy from the New York Times bestselling authors of Roomies. Olive Torres is used to being the unlucky ...More


Visit Our Blog
Browse A Little
PBR book reviews and Reading guides for book clubs
Visit out Etsy Shop
10 Books I Can't Stop Recommending