Gather initial thoughts and broad opinions about the book.

1. Play with Me blends screwball comedy with serious explorations of grief and trauma. How effective did you find this mix of tones? Did the humor enhance or detract from the emotional depth of Jennie’s and Garrett’s stories for you?

2. What was your initial impression of Jennie and Garrett? Did your feelings about them change as you learned more about their pasts and witnessed their relationship develop?

3. This book is part of the Playing for Keeps series, where each book focuses on a different couple within the same friend group. How did you feel this interconnected structure worked? For those who have read other series with a similar format, like Julia Quinn’s Bridgerton series (including The Duke and I and Romancing Mr. Bridgerton), how did this experience compare?

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

1. Has there been a time in your life when you felt you had to be inauthentic to protect yourself, as Jennie does with her sarcasm or Garrett with his quietness? How did that experience shape your interactions with others?

2. Jennie’s dream evolves from wanting a prestigious job in Toronto to opening her own studio in Vancouver. Think about a time when your own personal or professional goals shifted. What prompted that change, and how did it affect your sense of identity or happiness?

3. How does Garrett’s journey of finding his voice resonate with the ways people learn to express themselves over time? In what ways have childhood or family dynamics influenced your own communication style as an adult? 

4. Emily evolves from a perceived rival into a genuine friend for Jennie. Think about a time you formed an unexpected friendship. What circumstances brought you together, and what did you learn from that connection?

5. The story emphasizes the importance of a “chosen family” through characters like Cara, Olivia, and Adam. What role do supportive friendships play in your own life? How does the book’s depiction of this found family compare to your own experiences?

6. Princess Bubblegum is a cherished object that represents Jennie’s connection to her late father. Do you have a sentimental object that holds a powerful memory or connection for you? What makes it so meaningful?

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

1. How does the intense, hypermasculine world of professional hockey shape the characters’ behaviors and conflicts? In what ways does the novel challenge or reinforce stereotypes associated with athletes and sports culture?

2. Jennie’s trauma stems from having an intimate video taken and shared without her consent. How does the book’s portrayal of this experience and its long-lasting effects speak to contemporary conversations about digital privacy, consent, and cyberbullying?

3. Carter’s identity is tied to his role as his sister’s protector, which becomes a major source of conflict. What does the novel suggest about the complexities of familial responsibility and the challenges of letting go of traditional protective roles?

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

1. How does the alternating first-person narration between Jennie and Garrett influence your understanding of their relationship? What specific insights do you gain from seeing events from both perspectives that a single narrator couldn’t provide?

2. How does the author use the single word “Sunshine” to chart the entire emotional arc of Garrett and Jennie’s relationship, from sarcasm to love?

3. What is the role of Disney movies and songs in the story? How do these moments of vulnerability contrast with the tough exteriors the characters try to maintain?

4. Carter Beckett is a major obstacle to the central romance. In what ways does his overprotective and controlling nature serve as a foil to Garrett’s approach to Jennie? How does this juxtaposition develop Garrett’s character?

5. For readers familiar with Becka Mack’s other work, particularly the first book in the series, Consider Me, how does Garrett and Jennie’s story compare to Carter and Olivia’s? What thematic or structural similarities and differences did you notice?

6. Jennie’s sex toys serve multiple functions in the plot. How does their meaning and purpose in the novel evolve over time?

Encourage imaginative and creative connections to the book.

1. If you were to create a playlist for this book, what three songs would you choose to represent key moments in Jennie and Garrett’s relationship? What makes each song a perfect fit for a particular scene or emotional turning point?

2. Imagine you are designing the set for a film adaptation of Play with Me. What specific details would you include in Jennie’s condo and Garrett’s penthouse to visually represent their personalities and their emotional journeys?

3. The story ends with Carter comically interrupting Jennie and Garrett. Write a brief scene depicting the very next conversation between Carter and Garrett. How would they address the recurring awkwardness, and what would it reveal about their new dynamic?