Betting on You

Gather initial thoughts and broad opinions about the book.

1. What were your overall impressions of Betting on You? Did it meet your expectations?

2. Which parts of the book resonated with you most strongly, and which parts (if any) fell flat?

3. How does Betting on You compare to other romantic comedies you’ve read, especially those centered on teen protagonists and themes of family, like What Happened to Goodbye by Sarah Dessen or The Cupcake Queen by Heather Hepler?

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

1. Bailey and Charlie both struggle with change after their parents’ divorces. Have you ever experienced a time in your life when change felt overwhelming or destabilizing? How did you respond?

2. Bailey feels homesick not for a place but for a version of her life that no longer exists. Can you relate to that kind of nostalgic grief?

3. Charlie uses sarcasm and games to avoid dealing with emotional vulnerability. Do you think humor can be effectively used as a defense mechanism in real life? What coping strategies do you use in your own life?

4. Have you ever feared losing a friendship because of growing romantic feelings? Did the book’s depiction of this situation feel realistic or relatable to you?

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

1. How does the novel portray the emotional aftermath of divorce for teens? Do you think the story reflects real-life issues that children of divorce face?

2. The book indirectly critiques how adults sometimes underestimate the emotional impact of their decisions on their kids. Do you think this is common in real life? Why or why not?

3. Bailey and Charlie are faced with complex, adult situations like divorce and family changes. What does the novel suggest about how teens are expected to “mature” quickly in response to adult problems? How does it enter into contemporary conversation on this topic?

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

1. How did the dual-point-of-view narrative style impact your understanding of Bailey and Charlie’s characters? Did you feel closer to one than the other?

2. Analyze the use of games in the novel—not just literal games but emotional games as well. What do they reveal about the characters’ desire to escape or control their realities?

3. What role does Planet Funnn play as a setting? How does it contrast with the characters’ inner lives?

4. How does Painter use humor to address heavier topics like abandonment, anxiety, and fear?

Encourage imaginative and creative connections to the book.

1. Imagine if Charlie had responded to Bailey’s text messages instead of avoiding her after their intimate night at his apartment. What would he have said to comfort her? How would this have impacted the trajectory of their relationship?

2. Choose a character (Bailey, Charlie, or even Nekesa) and imagine their Instagram feed. What kind of photos, captions, and stories would they post during the events of the novel?

3. Imagine that Charlie, as he is at the beginning of the novel, has been hired to write the script for a romantic comedy—except he hates romantic comedies and believes that relationships are doomed. What’s the title? What’s the plot? Who are the characters? How does it end?