Problematic Summer Romance

Gather initial thoughts and broad opinions about the book.

1. Discuss what you liked most and least about Ali Hazelwood’s approach to the age-gap trope, particularly through Maya’s and Conor’s character arcs.

2. Compare this book to Hazelwood’s debut novel The Love Hypothesis. How do the books handle age gaps and the difficult pasts of the characters? Discuss how the settings (academia versus vacation) influence the progression of the romance.

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

1. Reflect on your response to the 15-year age gap between Maya and Conor. Why did you react this way? Did your reaction change over the course of the book?

2. Discuss your memories or expectations of being Maya’s and Conor’s ages (23 and 38, respectively). Do their experiences and the pressures they face align with what you remember/believe based on societal understanding?

3. Have you ever experienced a whirlwind summer romance or fling? How was it similar to and different from Maya and Conor’s experience in Sicily? If you haven’t experienced a summer romance, did Problematic Summer Romance validate or challenge your ideas of what such romances are like?

4. In Chapter 39, Maya and Conor debate how starting a romantic relationship is approached in America versus Europe. Which of their views aligns more closely with your views on dating and romance? Which of their approaches makes more sense to you? Why?

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

1. Analyze how Problematic Summer Romance comments on age gaps in romantic relationships. Discuss how such romances are viewed, why they are viewed that way, and what factors change how age gaps are externally understood.

2. Discuss the influence of Taormina and Mount Etna on the relationships in the story, both romantic and familial. How might the book have been different without the forced proximity of the wedding party or the environmental factors that influence the plot (such as Mount Etna’s eruption)?

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

1. Analyze Hazelwood’s use of the alternating timeline to build out Maya and Conor’s relationship. Did the back-and-forth add or detract from the tension?

2. Discuss Hazelwood’s choice to include a cast of quirky side characters. Do characters like Nyota and Minami round out the story or detract from the main romantic focus?

3. Explore how Taormina’s beauty enhances the romantic feel of the book, as well as the symbolism of the group being there for a wedding.

4. Compare and contrast Taormina and Scotland as symbols of where Maya and Conor’s relationship is during the book’s two timelines. Would the book have worked if the flashbacks were in Taormina and the main story was in Scotland?

Encourage imaginative and creative connections to the book.

1. If this book were adapted into a movie, who would you cast as Maya and Conor? Considering how age plays a hand in which parts men and women are cast in, do you think a Hollywood casting director would choose either of the people you picked?

2. Create a fictional travelogue for either Maya or Conor’s trip to Sicily. Discuss why you included what you did for each day of the trip and why that event is thematically symbolic to the story.