Mile High (Windy City, #1)

How does Zanders’s childhood trauma continue to impact him in the present? Compare his childhood dynamics with his present-day relationships with his sister, mother, and father. What issues is Zanders holding onto, and how does his bitterness impact his choices?

How do Stevie Shay’s relationships with her mother and her ex-boyfriend Brett warp her sense of self? Why does Stevie allow their opinions to impact her self-esteem?

Compare and contrast Zanders and Stevie. How do their parallels and disparities help them to create a balanced relationship?

The novel makes free use of several common tropes of the romance genre, including a mild version of the enemies-to-lovers trope. What other common patterns do you notice in the plot, and how does the author work to add creative twists to these dynamics?

Eli and Logan Maddison primarily serve as a support system for Zanders, but they also arguably serve as role models. Consider their own relationship history and evolution, and analyze at least three scenes in which they encourage Zanders to make positive changes in his life.

How does Zanders and Stevie’s love for one another transform both of them as individuals? Consider how the characters see themselves at the novel’s start compared to at the novel’s end.

How does Zanders and Stevie’s breakup force them to address their own issues head-on?

Compare and contrast Zanders and Stevie’s respective relationships with Active Minds of Chicago and Senior Dogs of Chicago. How do these organizations act as symbolic representations of the characters’ true selves?