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Book Club Questions for The East End by Jason Allen

Book Club Questions for The East End by Jason Allen

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The East End by Jason Allen highlights the socio-economic divide in the Hamptons, but also how the basic human need for connection and trust can transcend class differences. The following book club questions will have spoilers so if you haven’t read the novel yet, check out my spoiler-free review first. 

Corey Halpern, a local high schooler with a troubled home life, is desperate to leave the Hamptons and start anew somewhere else. His last summer before college, he settles for the escapism he finds in sneaking into neighboring mansions.

One night just before Memorial Day weekend, he breaks in to the wrong home at the wrong time: the Sheffield estate, where he and his mother, Gina, work. Under the cover of darkness, Leo Sheffield—a billionaire CEO, patriarch and the owner of the vast lakeside manor—arrives unexpectedly with a companion. After a shocking poolside accident, everything depends on Leo burying the truth before his family and friends arrive for the holiday weekend. Unfortunately for him, Corey saw what happened, as did other eyes in the shadows.

Secrecy, obsession and desperation dictate each character’s path in this spectacular debut. In a race against time, each critical moment holds life in the balance as Corey, Gina and Leo approach a common breaking point.

Let’s get into the discussion questions

  • Why do you think Corey broke into the various mansions? What was he really doing there? Why did he finally decide to go to the Sheffield estate?
  • Despite knowing that his wife is throwing a huge get together for Memorial Day weekend, Leo still brings his lover Henry back to his Hamptons home. Why did Leo bring Henry there?
  • Henry dies from an accidental overdose and both Corey and Angelique witnessed what happened. Why didn’t they go to the police? Are you surprised that Angelique trusted Corey throughout the whole experience?
  • Instead of facing consequences, Leo decided to keep Henry’s body buried on his property until he can figure out the next steps. Why do you think he wouldn’t face the consequences? What would have happened if he had gone to the police?
  • Corey’s mother Gina is trying to finalize a divorce to her abusive ex. She’s also dealing with her own alcohol and drug addiction. What were your thoughts on Gina and the descriptions of an addict? Do you think Gina will be able to get sober?
  • Despite his many flaws, Leo feels somewhat protective of Gina as she’s helped him many times in the past. Why do you think he told her the truth about Henry? Why did he trust her?
  • How would have Leo and Henry’s story played out differently if Leo allowed himself to live openly as a gay man? Why did he remain married to his wife even after the kids were grown?
  • What did you think about the descriptions of the differences between the economic classes in the Hamptons?
  • Let’s talk the ending—Leo’s fate and Ray becoming the fall guy for Henry’s death. What did you think about all of that?
  • What happens next for Corey, Angelique and Gina?

Additional recommendations

Here’s some other thought-provoking book recommendations.

Little Fires Everywhere by Celeste Ng is an impactful story about class, privilege and race.

In Shaker Heights, a placid, progressive suburb of Cleveland, everything is planned – from the layout of the winding roads, to the colors of the houses, to the successful lives its residents will go on to lead. And no one embodies this spirit more than Elena Richardson, whose guiding principle is playing by the rules.

Enter Mia Warren – an enigmatic artist and single mother – who arrives in this idyllic bubble with her teenaged daughter Pearl, and rents a house from the Richardsons. Soon Mia and Pearl become more than tenants: all four Richardson children are drawn to the mother-daughter pair. But Mia carries with her a mysterious past and a disregard for the status quo that threatens to upend this carefully ordered community.

When old family friends of the Richardsons attempt to adopt a Chinese-American baby, a custody battle erupts that dramatically divides the town–and puts Mia and Elena on opposing sides.  Suspicious of Mia and her motives, Elena is determined to uncover the secrets in Mia’s past. But her obsession will come at unexpected and devastating costs.

You can order the book on Amazon here. Find my discussion questions here.

The Lost Night by Andrea Bartz is a thrilling mystery full of depth and suspense.

In 2009, Edie had New York’s social world in her thrall. Mercurial and beguiling, she was the shining star of a group of recent graduates living in a Brooklyn loft and treating New York like their playground. When Edie’s body was found near a suicide note at the end of a long, drunken night, no one could believe it. Grief, shock, and resentment scattered the group and brought the era to an abrupt end.

A decade later, Lindsay has come a long way from the drug-addled world of Calhoun Lofts. She has devoted best friends, a cozy apartment, and a thriving career as a magazine’s head fact-checker. But when a chance reunion leads Lindsay to discover an unsettling video from that hazy night, she starts to wonder if Edie was actually murdered—and, worse, if she herself was involved. As she rifles through those months in 2009—combing through case files, old technology, and her fractured memories—Lindsay is forced to confront the demons of her own violent history to bring the truth to light.

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

Happy reading!

Feel free to discuss The East End below!