READERS GUIDE
Reader’s GuideThe Rom Con by Devon Daniels
Discussion Questions:
1. When we first meet Cassidy, she refuses to see Jack as anything more than her professional nemesis, but by the end of the book, she realizes that many of the assumptions she made about his character were wrong and that she’s found her match in the one she least expected. What factors or events do you think were most influential in changing her mind?
2. At first, Cassidy scoffs at the antiquated social customs of her grandmother’s generation, but she gradually comes to believe that much of the courtship advice has merit, even incorporating several of the suggestions into her relationship with Jack. Did any of Gran’s tips resonate with you, and if so, which ones?
3. Throughout the book, Cassidy struggles to accept Jack’s work and association with Brawler. Do you think it’s possible to compartmentalize negative feelings about a partner’s job, or is that type of conflict a relationship deal-breaker? Do you think Cassidy was right to judge Jack’s work harshly? Why or why not?
4. Cassidy and Christine have a strong sisterly bond, with Cassidy deeply valuing her older sibling’s advice. How do you think Christine’s opinion influenced Cassidy’s decision to take her relationship with Jack more seriously? How do you think Christine’s example helped encourage Cassidy to take more risks?
5. The book follows Cassidy on her journey from risk-averse to risk-taker in both her professional and personal life. What are some ways Cassidy grew and changed from the beginning of the story until the end? Would you describe yourself as a risk-taker or someone who plays it safe?
6. Cassidy opens up to Jack about feeling lonely and “left behind” as many of her friends get married and start families. Have you ever
dealt with feelings of insecurity about your peers’ personal or professional milestones, and if so, how did you navigate them?
7. Many women grew up reading magazines that published lists and quizzes similar to those mentioned in the book, like “125 Tips to Hook a Husband” or “Things to Do with Your Hands That Men Like.” Do you think these lists of tips are sexist and outdated, or do you think they
provide valuable advice? Has your opinion on this type of advice column changed over time?
8. One of the ways Cassidy attempts to behave like a stereotypical 1950s housewife is to cook Engagement Chicken. Have you ever done something similar to impress a potential partner? How do you think gender roles and responsibilities inside the home have shifted since the 1950s?
9. Many actresses from Hollywood’s “golden age” remain beloved icons and are as relevant in modern pop culture as they were eighty years ago, from Audrey Hepburn to Marilyn Monroe to Doris Day. Similarly, depictions of the archetypal 1950s housewife regularly pop up in contemporary books, films, and music. Why do you think people remain so captivated by this period in history and the concept of the perfect housewife? How have media depictions of wives and mothers evolved over time?
10. Cassidy enjoys a special relationship with her grandmother and treasures the extra time she’s able to spend with her. What do you think younger generations can gain from spending time with their elder relatives? What stories or family heirlooms have been passed down that hold special significance for you?
11. Fashion plays an important role in The Rom Con, with Cassidy’s wardrobe gradually morphing from the quintessential New York uniform of dark, sophisticated basics into the more colorful, whimsical, and feminine silhouettes of the fifties. How does Cassidy’s shift in style echo her personal and professional transformations?
12. In the epilogue, we see that Cassidy has been able to build a fulfilling home life with Jack while still achieving her professional dreams. What factors and decisions do you think contributed to her success in finding that balance? What obstacles do women typically encounter in their quest to “have it all”?
13. The contrast between the more formal and intentional courtship customs of the past and the more casual, convenience-based contemporary dating approach is a recurring theme in the book. What do you think are some pros and cons of modern dating culture versus old-fashioned, retro courtship?
14. The story’s setting plays a special role in The Rom Con, with scenes taking place at various famous New York City landmarks, from Arthur Ashe Stadium to Times Square to Central Park in the fall. What was your favorite scene or New York location to read about?
