Gather initial thoughts and broad opinions about the book.

1. Rewind It Back is the final installment of the Windy City series. For those who have read other books in the series, how did this story feel as a conclusion to the friend group’s journey, and did it meet your expectations for Rio’s story?

2. What was your immediate reaction to the reunion between Rio and Hallie at the hockey game? How did that encounter shape your feelings about their chances for reconciliation as you continued reading?

3. Consider the blend of sports drama and second-chance romance in the novel. Did you find one aspect more compelling than the other? How well do you think the author balanced the pressures of Rio’s professional life with the emotional weight of his past?

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

1. The tradition of making mixtapes is central to Rio and Hallie’s bond. Think about how you preserve important memories in your own life. Do you have a special object or ritual that helps you “rewind it back” to a meaningful time?

2. Hallie makes immense sacrifices to become her father’s caregiver. Have you ever had to balance your personal goals with the needs of your family or loved ones? How did you navigate that responsibility?

3. Rio’s found family of friends provides the unconditional support he needs to heal and grow. Withing your own life, who is part of your chosen family? Consider sharing a story about an experience that brought you together or that showed you how much these individuals mean to you.

4. Over the course of the novel. Mia journeys from bitterness to forgiveness. Have you ever had an experience where learning new information completely changed your perspective on a past event or a person?

5. Both Rio and Hallie feel defined by the choices they made as teenagers. In what ways do you see your younger self influencing the person you are today?

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

1. This book is part of the “BookTok” sports-romance phenomenon. In what ways does Rewind It Back reflect the popular elements of this subgenre, such as the driven athlete hero or the interconnected friend group? Why do you think these stories have become so popular?

2. What does the novel reveal about the immense financial and emotional burdens placed on young-adult caregivers? How does Hallie’s story comment on the societal systems meant to support families facing major illnesses?

3. Rio struggles with balancing the hyper-masculine image of a professional athlete with his deeply sentimental and vulnerable nature. What message do you think the novel sends about modern masculinity and the freedom for men to express loyalty and deep emotion?

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

1. How does the alternating use of past and present timelines shape your understanding of the characters’ motivations? Did you find that the flashbacks enriched the present-day narrative, or were they disruptive to the story’s flow?

2. The roof connecting the main characters’ childhood homes is a private sanctuary. How does the meaning of this space transform throughout the novel?

3. Discuss the novel’s antagonists, Steph Hart and Rio’s father. Though their affair happens largely off-page, their actions drive the main conflict. How effective are they as villains when they have such a limited presence in the story itself?

4. The “interconnected standalone” series model is very popular in contemporary romance. For readers familiar with this structure, how does Tomforde’s use of it in the Windy City series compare to other series, like those by Elle Kennedy? What do you see as the strengths of this format?

5. The full truth about Hallie’s sacrifices is revealed very late in the book. Do you think the pacing of this reveal was effective? How might your reading experience have changed if you had known the whole story from the beginning?

Encourage imaginative and creative connections to the book.

1. Hallie is an interior designer who transforms Rio’s house to reflect their shared past and future. If you were to design a room representing a significant relationship in your life, what key elements or objects would you include to tell its story?

2. Imagine you’re writing a scene from the perspective of a secondary character like Wren or Indy. What would they notice about Rio and Hallie’s dynamic during their reunion that the main characters might not see themselves?

3. Rio creates a new playlist to mark the important moments of their reconciliation. What three songs would you put on a playlist titled “Rewind It Back” to capture the essence of Rio and Hallie’s story, and what moment would each song represent?