1. Why do you think the author chose to tell parts of the story through pages of Franny's Filofax planner? What elements does it add to the novel?
2. Is setting a deadline on your dream a good idea? Or is it unrealistic? Do you think it ultimately helped or hindered Franny's career?
3. Although he only appears as a recorded voice on the answering machine, Clark plays an important role in the story. What does his and Franny's back-up plan represent? What does his engagement force Franny to do?
4. For parts of the novel, Franny adapts to a situation by playing a character she is not. When is she being true to herself? When is she most happy?
5. Why didn't Franny sign with Barney Sparks? What would you have done in her position?
6. Franny appreciates the bridge on the D train because it helps her put things in perspective. Do you have a D train bridge in your life? What is it?
7. Do you agree with Franny's interpretation of love triangles on page 281?
8. Penelope and Franny have an interesting relationship throughout the novel. In what ways does it change? What does Penelope help Franny understand?
9. On page 307, the taxi driver remarks, "How'd it get this far and not go pop?" Why does this resonate with Franny? What could it represent in her life?
10. What does everyone else see in Franny that she doesn't see for herself?
11. On page 335, Franny's father tells her, "Imagine the best for yourself now and then, won't you, hon?" Discuss the importance of having a positive attitude, and how this changes for Franny.
12. The characters throughout the novel have their own individual takes on authenticity. What does it mean to James? How is that different from what it means to Dan, Franny, or Penny? VVhich definition do you agree with? Is it possible to be authentic in an industry that is in itself an artificial craft?
13. How has Franny changed by the end of the novel? What were her most transforming moments? Who most strongly influenced her?
14. Of all the themes in the novel--dreams, hope, friendship, believing in yourself, etc.--which did you find the most compelling? What do you think is the takeaway lesson of the book?