Where the Grass Is Green and the Girls Are Pretty Reading Guide

1. Which character did you most like or relate to in this novel and why? Also: who did you relate to the least and why?
2. At its core, Where the Grass is Green and the Girls are Pretty is about family. Although families can be strong and uplifting support systems, Peyton's actions negatively affect several of her family members. How does the novel reconcile their conflicts?
3. The author's close relationship with her sister inspired her to write a novel that delves into that dynamic. Do you have a sister or a close friend who you thought of while reading? In what ways is your relationship similar to Peyton and Skye's? How is it different? What were your favorite scenes between them?
4. Skye graduated from a private liberal arts school, Amherst College, and Peyton graduated from a branch campus of Penn State after completing a year of community college. Regardless of the stereotypes associated with each of these undergraduate schools, Peyton becomes a renowned news anchor. Do you think she was at a disadvantage having gone to a less prestigious school than her sister? Why or why not? Why was Peyton so adamant that Max, who wanted to attend film school, go to a prestigious Ivy League school?
5. To what extent do you think Peyton committed admissions fraud for Max's happiness as opposed to her own? Why do you think that?
6. The need to keep up appearances is a common theme: Peyton's obsession with her appearance, Jim "arranging his face into an impressive façade of empathy", the waiter in the restaurant in the opening scene putting on a "bad fake French accent," Henry rescinding his offer due to "the appearance of impropriety." In what other ways do the characters wear masks and why? In what ways have you experienced this in your life?
7. Why do you think the author decided to include Max's perspective in the book? Did her viewpoint alter your perception of her mother, Peyton? Of her Aunt Skye?
8. Lauren Weisberger is known for her social satire and wit. Were there any scenes that provided comic relief? Did you enjoy her social commentary on her fictional upper-class suburb? Why or why not?
9. Skye states she moved to Paradise for the great public schools but laments the lack of opportunity to connect with "all different kids, from so many varied backgrounds and perspectives." What are the trade-offs of living in a suburb like Paradise rather than in a more economically and socially diverse city?
10. Skye keeps secrets from Gabe (e.g., her debt and the possibility for adoption) and Peyton keeps secrets from Isaac (e.g., committing admissions fraud). In your opinion, is it ever okay to keep secrets from partners?
11. Peyton's and Isaac's affairs get played out in the "court of public opinion." Do you think it is fair that celebrities receive this level of scrutiny outside of the legal system? Why or why not?
12. Do you think Peyton made the right choice in turning herself in? Why or why not? Should she should have turned herself in much sooner?
13. Do you think Peyton is ultimately a good person? Are the sum of your actions what make you a good person? Can one action define you forever?
14. At the end of the novel Peyton finally realizes "how wrong it [her crime] was, on every level." What do you think helped lead her to this realization? Were you surprised by the ending?
15. If Where the Grass is Green and the Girls Are Pretty were made into a movie or TV series, which actors would you cast in the lead roles? Did you get the reference to a popular 80s song that inspired the title and the name of the town?

Unless otherwise stated, this discussion guide is reprinted with the permission of Kids@Random. Any page references refer to a USA edition of the book, usually the trade paperback version, and may vary in other editions.