Analyze some of the songs that the main characters include on their CDs, mixtapes, and playlists. How do these lyrics shape the mood or reflect the characters’ situations?

Citing specific evidence from the text, analyze how Tomforde uses structural and narrative techniques to create suspense, heighten romantic tension, and advance characterization.

In what ways does Rewind It Back align with the conventions of the romance genre, particularly the sports romance and “second chance” subgenres? In what ways does Tomforde subvert generic conventions, and how do these authorial decisions impact the novel’s overall meaning?

Contrast the function of the “found family” of friends with the biological families of Rio and Hallie. How does the friend group support the novel’s structure and themes?

Select two secondary male characters who provide alternative models of masculinity that challenge the toxic example set by Rio’s father and the stereotype of the hypermasculine athlete. How do these supporting characters advance Rio’s growth and Tomforde’s message?

As the final book in the Windy City series, Rewind It Back functions as both a self-contained romance and a conclusion for a larger ensemble. In what ways does the presence of established couples from previous books enhance the central love story?

How does the novel compare to other sports romances, such as Elle Kennedy’s The Graham Effect or Rachel Reid’s Role Model? How do the different authors use the realm of professional sports to explore concepts like identity, healing, and family?

How does the novel’s use of contrasting public and private settings highlight the tension in Rio’s life, and how does Hallie’s work as an interior designer literally and figuratively reshape Rio’s private world?