Gather initial thoughts and broad opinions about the book.

1. The novel blends a high-stakes sports setting and a cozy found family story with heavier themes of grief and parental anxiety. Did you find this combination effective in creating a compelling romance? What aspects of the story resonated most strongly with you and why?

2. How did you find Caught Up compared to other books in the Windy City series, like Mile High or The Right Move, if you’ve read them? In what ways does this story feel unique within the interconnected universe Tomforde has created? If this was your first book in the series, did it make you want to read the others?

3. What scene or moment has stayed with you most vividly after finishing the book?

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

1. Miller’s professional success leads to a creative crisis where she feels overwhelmed by pressure. Have you ever experienced a time when achieving a goal brought unexpected stress? Within your own life, what brings you joy and fulfillment, and how do you rejuvenate yourself when you experience burnout? 

2. Ryan, Indy, Zanders, Stevie, and Rio become a found family for Kai and Miller. Who’s part of your chosen family? Consider sharing a story about what brought you together.

3. Miller greatly looks up to Monty, who adopted her when she was five. Who’s someone who has made a positive difference in your life during a difficult time? How have they shaped you?

4. Miller identifies as a “runner,” someone who leaves situations before they can become too attached or painful, while Kai openly expresses his feelings and desires commitment. Which of these perspectives do you relate to more and why?

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

1. In what ways does Kai’s character challenge traditional ideas of masculinity? How does the novel’s portrayal contribute to conversations about modern fatherhood?

2. The demanding schedule of Major League Baseball is a major source of conflict for Kai. What does this portrayal reveal about the personal costs that often accompany elite professional careers, both in sports and other fields?

3. What does the novel seem to suggest about modern “hustle culture” through Miller’s experience in the high-end culinary world? How does her ultimate choice to open a small, local bakery serve as a commentary on different definitions of success?

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

1. What is the significance of Kai’s kitchen in the novel? How does it transform from a sterile, unused space into the emotional heart of their home as the story progresses?

2. How does the motif of baking chart Miller’s emotional journey? Consider the difference between her failed, high-pressure desserts and the simple recipes she bakes with Max.

3. The story is told from the dual perspectives of Kai and Miller. How did having insight into both of their internal thoughts and insecurities affect your understanding of their relationship, especially during moments of miscommunication?

4. How does Isaiah’s carefree, playboy persona serve as a foil to Kai, highlighting the profound changes Kai has undergone since becoming a father?

5. In what ways does the meaning of the baseball field evolve as a motif of The Conflict Between Professional Ambition and Personal Fulfillment? How does it shift from a space representing the tension between his career and family to one where those two worlds can successfully merge?

Encourage imaginative and creative connections to the book.

1. Miller’s final magazine spread includes recipes that are deeply personal, like a tiramisu in honor of Kai’s late mother. If you had to choose three recipes to tell your own life story, what would they be and why?

2. Imagine you are part of Kai’s close-knit friend group and are present at the Sunday family dinners. What advice would you give Kai about his feelings for Miller during the summer? What might you say to Miller to encourage her to stay?