1. How has Carrie’s past affected her decisions and ability to choose a life path? Which characteristics does Carrie share with Rose, and how are they different from each other?

2. Shaffer is known for creating well-developed, convincing female characters. Which of these women did you most identify with? Sympathize with? Disagree with?

3. Carrie’s best friend, Zoe, states that Carrie has “mommy issues.” Why do you think mother-daughter relationships are often so complicated? How do you feel about the way Rose raised her daughter?

4. Why does Rose hold back so much family history from her daughter? How does Carrie’s eventual discovery of what happened affect how she perceives her mother?

5. Rose is a complicated, dualistic character with a love-hate relationship with wealth and fame; she is constantly telling Carrie to be wary of one’s ego. What, in your opinion, made Rose shun her lifestyle after Bobbie’s death? Do you think her choices made her happy?

6. What do you make of Rose’s multiple copies of the same dress? What was her reasoning behind this?

7. How does Mifalda change over the course of the novel? How do you think she came to her decision regarding Lu and her new baby, and could you imagine doing the same thing in her position?

8. How do you feel about Lu’s picking career over family? What other sacrifices do the women in Serendipity make in their lives? What betrayals do they make?

9. What attracts Rose so deeply to Bobbie Manning? How would you characterize their relationship, and in which ways does it change over time? Why does she go to such great lengths for him? On a similar note, what attracts Carrie to Howie?

10. How does Shaffer use ice skating as a symbol, for both Mifalda and Rose?

11. Carrie asks herself “Why do I always feel like I’m settling for an empty basket when I want one that’s full? Why can’t I let myself be happy?” What do you think the answers to these questions are, and how do you envision her future at the end of the book?

12. “Mama, Lu, and Rose,” Carrie’s uncle Paulie states, “standing in a line. Three young girls, handing down all the good and bad from one generation to the next. They couldn’t get away from each other.” What did each woman pass down to her daughter? What role does family legacy play in this novel, and is it portrayed positively or negatively?

13. One of this novel’s themes is that women can’t do it all --- career, family, love --- successfully. Today, many women seem to be revisiting this idea. Do women have to choose their priorities? What about men?

14. If you were casting the movie Serendipity, whom would you pick for actors?