What issues are raised by Mali's sudden appearance at Casey's apartment?
Casey agrees to let Mali spend a night with her, believing it's a way to keep an eye on her. Do you think Casey made the right decision? Why or why not? How would you handle this situation?
Casey believes women love men who aren't available because it makes the chase more challenging. Do you agree? Have you ever encountered a woman who seems interested in your significant other despite your presence by his side? How does this affect the notion of sisterhood?
Casey begins to realize winning John Paul has become more important than being with him. What role do you think he plays in the book? What role does the young firefighter Josh play? Compare and contrast both men and their relationship to Casey.
Who is the insignificant other? Explain your choice.
How did the author utilize the urban environment in which Casey and her friends live in? Was this done effectively?
Early in the novel Casey tells Ariadne all of the strong women she admires are more messed up than she is. They aren't better at life, just better at hiding who they are. Have you ever discovered this to be true about someone you admire? How did you react to this realization?
Compare and contrast Casey and Ariadne's outlook on life. What role did Ariadne play in Casey's life?
Have you ever wondered about the private lives of your teachers or professors? Have you ever had romantic feelings for a professor or student? If so, how did you handle your feelings?
Casey has a wry sense of humor. Did you find her narrative funny? Ironic? What examples of humor did you come across in the novel?
Are group friendships harmful/helpful to relationships? How would you maintain a relationship so deeply rooted in group dynamics?
How do Mali, Polo, Gabriella and Ariadne represent womanhood collectively and individually?
Who do you think called Casey at the end of His Insignificant Other? Why did she choose not to answer the phone?
Do you think Casey should have chosen between Josh and John Paul? Were you happy with her decision to move on and start an independent life without a man? Discuss your answers.