Gather initial thoughts and broad opinions about the book.

1. The novel’s title, Tropesick, immediately signals its self-aware approach to romance conventions. How did this metafictional premise shape your initial expectations for the story? Did you find the blending of a sincere romance with a commentary on its own genre effective?

2. What was your reaction to the supernatural twist revealing Meredith as a ghost? Did this element enhance the story for you, or did you find it jarring in an otherwise contemporary romance?

3. The guide notes a trend in novels featuring author protagonists, like Emily Henry’s Beach Read, which is mentioned in the story. How do you think Tropesick fits within this subgenre? In what ways does it use the “author” character differently or similarly to other books you’ve read?

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

1. How does Katie’s use of a “sunshine” personality as a shield against trauma resonate with you? Think about a time you might have presented a certain persona to the world to protect yourself.

2. For Katie and Tyler, their shared passion for writing becomes the only safe space to reconnect. Have you ever found that a shared project or creative interest helped you build or repair a bond with someone? What is it about creating something together that can foster connection?

3. How does Tyler’s journey to forgive himself and rewrite the “false narrative” that he is broken challenge your own negative self-perceptions?

4. The novel explores how anniversaries and rituals can keep grief active. Tyler’s annual tradition of honoring Mikey is a private act of penance until he shares it with Katie. How do you think personal or cultural rituals help people navigate loss and memory?

5. Meredith warns Tyler not to let a great love get away because of fear, as she did. Think about a moment when fear might have held you back from an opportunity or connection. How do the characters’ choices about facing their fears connect with your own experiences?

6. How do you feel about the idea of a “second chance” in relationships, which is so central to this novel? Do you believe it’s possible to truly start over, or does the past always remain a part of the present?

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

1. The novel grounds Mikey’s story in the real-world American opioid crisis, tracing his addiction back to a sports injury. How did this specific context affect your understanding of the Caruso family’s tragedy and Tyler’s guilt? What does the book suggest about how a widespread public health issue can cause such private devastation?

2. What questions did Tropesick raise for you about authorship and creativity after pulling back the curtain on the commercial practice of ghostwriting?

3. The story is deeply engaged with the romance tropes popularized on platforms like #BookTok. Do you see the novel as a celebration of these tropes, a critique of their formulaic nature, or something more complex? How does it comment on the way readers now engage with and categorize books?

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

1. How did you interpret Meredith Bradford’s motivations for orchestrating Katie and Tyler’s reunion? Is she a mentor, a manipulator, or a tragic ghost, and does her intervention undermine the authenticity of their love story?

2. What is the significance of the carriage house as a symbol in the novel? How does its meaning evolve from a forbidden writing studio to the place where Tyler discovers the “plot wall” and the truth about their story?

3. In what specific ways do the pink walkie-talkies, as a symbol, allow Katie and Tyler to rebuild intimacy when face-to-face communication is too difficult?

4. How did the narrative structure, which alternates between the present day, flashbacks, and fictional interludes, impact your reading experience and understanding of the characters’ history?

5. Carolyn Caruso functions as the story’s primary antagonist. Do you see her as a purely villainous figure, or does the novel allow for a more complicated understanding of her actions, which are driven by all-consuming grief?

Encourage imaginative and creative connections to the book.

1. Imagine you are adapting Tropesick into a movie. Which scene do you think would be the most challenging to translate to the screen, and how would you approach it? Who would you cast in the lead roles of Katie, Tyler, and Meredith?

2. What would Katie and Tyler’s lives look like in a short epilogue set five years after the book ends? Are they still writing together, and how has their relationship with Katie’s family evolved?

3. At the end of the book, Katie and Tyler find the finished manuscript of Tropesick with a final note from Meredith. If you could have added one last piece of advice or one final observation to her note, what would it have been?