The following version of this book was used to create the guide: Jackson, Jenny. Pineapple Street. Viking, 2023.

Jenny Jackson’s third person limited narrative, Pineapple Street, follows the lives of three women in the Stockton family as they navigate life in the upper echelon of Brooklyn society. At the outset of the novel, Sasha struggled to fit in with her husband’s family. While they lived in Cord’s childhood home, the limestone was still cluttered with his parent’s belongings. Georgiana and Darley tolerated Sasha’s presence, but they privately called her the Gold Digger. They laughed at Sasha inability to dress for social functions and did not make eye contact with her in conversation. Georgiana, the youngest Stockton, worked for a nonprofit organization and had a crush on her coworker, Brady. They began to banter at the office, and he invited her to play tennis. Their friendship soon turned into a friends-with-benefits relationship, though Georgiana was privately in love with him. Meanwhile, Darley was a stay at home mom who quit her career to raise her family full time. When she learned that Malcolm was fired from his job, she began to worry about money for the first time in her life. When she and Malcolm married, she signed her trust fund to her children because she did not want to ask her fiancé to sign a prenup.

As she worried about telling her parents that her husband was unemployed, Darley began to spend more time with Sasha. They met up in the park and chatted over lunch. While Darley was suspicious of her sister-in-law, she felt comfortable around her as they spent more time together and confided to her about Malcolm’s work situation. When Georgiana discovered that Brady was married, she pretended to call off their affair, but secretly kept sleeping with him. She was devastated when he died in a plane crash and unsure who she could turn to. When she told Sasha about her heartbreak, she made her promise not to tell the other Stocktons. At a cousin’s wedding, Sasha overheard her sisters-in-law talking with Bubbles who revealed that they always call Sasha the Gold Digger. She resolved to stop trying to befriend them and win their approval. As Georgiana coped with her heartbreak, she began to drink more and take Valium. At a party with her friends, she kissed her former classmate Cutis McCoy. Shortly after, her mother showed her an interview with Curtis in which he talked about liquidating his trust fund and donating the money to charity. When Georgiana was visibly drunk at a family gathering, she told her family to ask Sasha about it. Sasha revealed that Georgiana had been sleeping with her, now deceased, married coworker. The Stocktons blamed Sasha for keeping Georgiana’s heartbreak a secret and Cord shut himself in the bedroom to have private conversations with his family.

Sasha felt more isolated and decided to visit her family in Rhode Island when she learned that her father was in the hospital. When Darley visited her brother at Pineapple Street, he was having the family’s belongings removed to please Sasha and told his sister about Sasha’s father. Darley sent an extravagant floral arrangement to Sasha and apologized for calling her a gold digger. After Georgiana began to spend more time with Curtis, she started to question her own privilege and formed a plan to donate her own trust fund to not-for-profits. At the close of the novel, Darley and Malcolm moved into the Pineapple Street home, Cord promised to defend Sasha around his family and Georgiana was dating Curtis and starting a fund to provide reproductive health care to women in Pakistan.