Gather initial thoughts and broad opinions about the book.

1. How does In Her Own League compare to other contemporary sports romances you may have read? What common tropes or themes did you spot?

2. Discuss who your favorite and least favorite characters are.

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

1. Reese and Emmett feel conflicted for most of the novel because of how their personal desires conflict with their professional obligations. Have you ever felt torn between following your heart and living up to the expectations placed on you, either personally or professionally? What did you ultimately decide to do, and why?

2. Reese faces a lot of pushback from others when she first takes over the team. Have you ever felt out-of-place or as though you didn’t belong somewhere simply because of the way others treated you? How did you resolve the situation?

3. Reese has her safe space in the dugout where she goes to hide and reflect. Do you have a safe space you retreat to in emotional or stressful periods? What makes this space ideal for you?

4. Milo feels a lot of pressure during his first game, and performs poorly as a result. Have you ever found yourself wrestling with stress or nerves when confronting a new challenge? Did you succeed or fail, and what did you learn from that experience?

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

1. How do the double standards and unfair treatment that Reese faces as a woman in a male-dominated field reflect the current social realities faced in our own world?

2. Consider how masculinity is portrayed through the male characters in the novel. In what ways does the book reinforce or challenge current ideas of masculinity, particularly in relation to emotional vulnerability and/or support for women’s success?

3. How does the novel portray the balance between personal fulfillment and professional success? How might that reflect current attitudes and debates around what women are “allowed” to prioritize?

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

1. How does the author’s use of dual perspectives impact the narration and characterization in the text? What do these dual perspectives reveal about the similarities and differences between Reese and Emmett?

2. Analyze the depiction of family ties in the book, such as Reese’s bond with Arthur, Emmett and Miller’s dynamic, or the “found family” in the baseball team. What does the novel suggest about the nature and role of family ties in individual lives?

3. The media is a constant external pressure in the characters’ lives, often shaping narratives about Reese and the team, whether true or false. How does the novel explore the idea of narrative, persona, and/or public perception? 

4. Compare and contrast In Her Own League with another novel from the Windy City series. What key themes and ideas do both texts explore? How are they different or similar in their handling of the contemporary sports romance genre?

Encourage imaginative and creative connections to the book.

1. Imagine another spinoff possibility for the series. Which side character that you’ve met either in this novel or elsewhere throughout the Windy City series would make a good story? What tropes would their romance entail? What kind of person would their ideal love interest be?

2. If you were one of the advisory board members, how would you have handled the meetings throughout the novel? What alternate suggestions would you have made to Reese to help her strengthen her franchise?