1. Which of the “Single Girls” did you most identify with, and why?

2. The novel explores what it meant to be a “single girl” in a changing America. How did each woman define, discover or pursue freedom differently?

3. Did the book change your perception of the 1960s as a glamorous decade? Why or why not?

4. Which moments best illustrated the subtle ways women were underestimated or controlled? And were there scenes that made you reconsider how far women have or haven’t come since then?

5. The novel often shows women doing the work while men receive the recognition. Do you think that dynamic has changed today?

6. Did the romantic relationships in the book feel empowering, limiting, transactional or something more complicated?

7. The author has described the setup of the novel as “Helen being like the sun and the other single girls like planets revolving around her.” How did you interpret Helen’s influence on the characters?

8. The novel also introduces a series of “single girls” who briefly intersect with the main story, including Nikki, the Park Avenue Girl; Nadine, the actress who unexpectedly appears at David’s home; and Ursula, who is making a quiet but radical choice for her life. What do these characters add to the narrative, and why do you think the author included them?

9. Why do you think the “Cosmo girl” became such a powerful cultural archetype?

10. How does the novel compare with stories like “Mad Men,” The Devil Wears Prada or Valley of the Dolls?

11. Do you think we leave Helen in a place where she is truly “liberated” from her past, or will it continue to hold the same power over her?

12. Finally, what do you think the candy symbolized? And why do you think the author chose to focus on the famous Delacroix painting, Liberty Leading the People?

And just for fun…

1. Are you a mouseburger? Why or why not?

2. Have you ever soaked in a champagne-glass hot tub? If not, would you want to?

3. Which character do you think would have the strongest social media presence today --- and what would her Instagram or TikTok look like?

4. If the novel were adapted into a television series, who would you cast?

5. Did you take the Cosmo coverline quiz? Results?

6. What moment most surprised you, made you laugh, or stayed with you emotionally?

7. If you could ask John Searles one question about the book, what would it be?