1. Is Paul a sympathetic character in any way? How would the novel be different if told from his perspective? Sophie tells her sister Delia on page that Natalie suits Paul "in every way better than I do." Is Paul the real villain of the piece, or simply a mixed-up guy who realizes that he has made a mistake fairly early in his marriage?

2. The book presents a "glamorous and super-competent" career woman figure (Sophie's friend Marta) and an "office schemer" -- the pert, and conniving Natalie. How are Natalie and Marta foils for Sophie and Sophie's approach to career and romance? How are Marta and Sophie's sister Delia foils for each other?

3. How does Sophie's search for a true vocation relate to her search for real love? Does Sophie's search for meaningful work propel her relationship with Ned, or vice versa?

4. Did you feel regret when Sophie turns down a second chance at love with Rory? Sophie says, "I could picture the night [with Rory], how good it would be. I just couldn't see farther....I could not picture SETTING OUT with Rory." What does Sophie mean by this observation? What do you think are Rory's true feelings for Sophie?

5. Pepper Stoddard is a classic figure of comedy: the difficult mother-in-law. Is Pepper believable, and could Sophie have handled her more adroitly for a different result? Do you foresee Natalie getting along with Pepper more amicably than Sophie has, or would Pepper be critical of ANY daughter-in-law?

6. At what point in the book does Ned realize his feelings for Sophie? Why doesn't Ned declare himself sooner?

7. Sophie's feelings about the city of Portland, Maine, change over the course of the book. At the end of the novel, what image of the city is the reader left with? Is the city meant to be portrayed as a true-to-life locale, or should it be seen by the reader as more of a reflection of Sophie's mental and emotional state?

8. How does Donald help Sophie take a stand for herself? Did you feel Donald grew and changed through the course of the novel or is it Sophie's reaction to Donald that changed?