The Love Wager

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

1. How does The Love Wager compare to other romantic comedies you’ve seen or watched? What are some of the conventions you think are most successful?

2. How did you respond to Jack and Hallie’s fear that introducing sexual intimacy would ruin their friendship? Do you think men and women can be good friends?

3. What about Jack and Hallie’s adventures in dating resonated with you? Have you ever used an app or a different kind of matchmaking service to find dates?

4. What are your thoughts on the friends-to-lovers trope in romance novels? How does Painter’s use of this convention compare to that of other novels, like Addicted to You (2013) by Becca and Krista Richie or Hook, Line, and Sinker (2022) by Tessa Bailey?

5. What do you make of the fact that Jack and Hallie’s connection began as casual sex, then moved to platonic friendship? Do you know of any relationships like this that have been successful? Do you find the premise realistic?

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

1. How well do you think this book represents what modern dating is like? What adjustments might Painter have made to suit her story?

2. What influence do you think texting and app messaging have on in-real-life relationships? How important are these methods to modern communication?

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

1. What did you think of the allusions to Jane Austen’s Pride and Prejudice and its film adaptations? What context did that add to Jack and Hallie’s relationship?

2. Discuss the role of the secondary and supporting characters as personal mentors and advocates for the romance. You may wish to focus on a specific foil, like Ben or Alex for Jack and Ruthie for Hallie.

3. How do Jack and Hallie mature independently, and how does that growing maturity make them more suited as romantic partners?

4. Discuss the humorous tone and comedic moments in the book. How do those work to develop the romance?

5. What do you think of the fake relationship trope? What does it allow the characters to express about their real feelings that they don’t feel free to say otherwise?