How to Kill a Guy in Ten Dates

Shailee Thompson

How to Kill a Guy in Ten Dates

Shailee Thompson
55 pages1-hour read
Fiction
Novel
Adult
Published in 2026

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Book Club Questions

Content Warning: This section of the guide references graphic violence and death.

General Impressions

Gather initial thoughts and broad opinions about the book.


1. The story draws on conventions from slasher films like Scream and Psycho while its title and chapter epigraphs are plays on rom-coms like How to Lose a Guy in 10 Days, When Harry Met Sally, and Love and Basketball. What aspects of the blend worked best or felt the most surprising to you?


2. Which scene or image from the massacre at Serendipity struck you the most forcefully, and why?


3. How satisfied were you with the novel’s ending and the epilogue? Did it feel like a fitting conclusion to Jamie’s ordeal?

Personal Reflection and Connection

Encourage readers to connect the book’s themes and characters with their personal experiences.


1. Jamie relies on her “How to Survive a Slasher” poster to make sense of the chaos around her. Think about a time you’ve faced a stressful or confusing situation. Did you find yourself looking for a set of rules or a familiar framework to guide you?


2. The characters are driven to the speed-dating event in part by dating app fatigue and a desire for more authentic connection. Have you or others you know experienced challenges dating in the digital age? How did the novel’s portrayal of the search for intimacy resonate with your experiences?


3. Jamie and Laurie’s friendship is a key factor in their survival. Do you have a friend whose support allows you to do things that might otherwise feel impossible?


4. In the novel’s climax, Jamie embodies two very different archetypes—the Leading Lady and the Final Girl. Which archetype is most like your personality?

Societal and Cultural Context

Examine the book’s relevance to societal issues, historical events, or cultural themes.


1. John believes he is owed a perfect love story—a belief he uses to justify extreme violence. Where do we see cultural narratives that celebrate obsessive male pursuit as romantic? In what ways does this novel serve as a critique of that trope?


2. What commentary do you think the author is making about modern anxieties surrounding vulnerability and personal safety in the search for a romantic partner? How does the “no-device” policy at the event contribute to this commentary?


3. When Wes reveals that he is a police officer, it fractures the group’s trust. What does the novel suggest about our cultural expectations of law enforcement and other authority figures in a crisis? How does the novel subvert the classic “hero cop” archetype?

Literary Analysis

Dive into the book’s structure, characters, themes, and symbolism.


1. The novel is a piece of metafiction, constantly drawing attention to its own use of genre conventions. How did Jamie’s academic narration and her knowledge of slasher rules affect your experience as a reader?


2. What makes the killer’s pink heart-eyed mask such a dominant symbol for the novel’s themes? How does it capture the fusion of romance and terror that drives the story?


3. John is meticulously crafted as an endearing, “[l]ate eighties Bill Pullman cute” romantic lead before his reveal as a killer (27). Why does the author rely on such specific movie references to create a concrete image? Does this reference risk alienating readers who are unfamiliar with the topic?


4. Jamie connects with both John and Wes over classic romantic comedies like While You Were Sleeping and Miss Congeniality. How does the novel use these specific film references to build, and later subvert, expectations about who the romantic hero should be?


5. How does the physical setting of the Serendipity nightclub amplify the novel’s horror and suspense and reflect the psychological entrapment of the characters?

Creative Engagement

Encourage imaginative and creative connections to the book.


1. Design the “How to Survive a Slasher” poster that hangs in Jamie’s apartment. Based on the events of the book, what new “rule number eleven” would you add to the list?


2. If Laurie were to create her documentary about the Serendipity massacre, what would the film’s central message or argument be? Who would she interview, and what story would she be most focused on telling?


3. The epilogue gives us a snapshot of Jamie’s life eight months later. Write a short scene that takes place a year after that. What would Jamie, Wes, and Laurie be doing?

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