1. The novel opens and closes with a first-person narrative by Carmen. Why do you think the author selected this character to frame the story? If you could change it, would you select another character, and if so, what would he or she say? Or do you think Carmen’s is the best viewpoint to begin and end the novel?
2. “For some reason our lives were marked by summers. . . . Summer was the time when our lives joined completely, when we all had our birthdays, when really important things happened” (p. 5). What is the significance of the Sisterhood’s first summer apart? Why is it so important that the four friends have individual adventures? Do you think they would have remained close if the Pants had not been a part of their lives?
3. Of the four girls, whom are you the most like? The most different from?
4. Epigraphs (short quotations) from a variety of sources—song lyrics, remarks by real-life personalities, fictitious sayings by the novel’s characters—are used to separate sections of the book. Which one is your favorite and why?
5. Carmen’s discovery of a new blond stepfamily comes as quite a shock. How could her father have better handled this news? Would it have made a difference to Carmen?
6. In the movie It’s a Wonderful Life, George Bailey sees what the world would have been like had he not been born. Author Ann Brashares has said that the character of Bailey was inspired by this film. How would Tibby’s life have been different if she had not met Bailey?
7. Lena is described as quite beautiful. How do you think this affects her friendships? Have you ever been friends with someone who is noticeably more or less attractive than you are? How did it make you feel?
8. Bridget feels powerful as she pursues Eric, but her actions leave her fragile and uncertain. Do you think that by the end of the story, Bridget is able to take back some of her power? Why or why not? What role do you think Bridget’s friends will play in her recovery?
9. In the novel, the Pants take on a life of their own. Each of the girls in turn feels loved and comforted by them, as if the Pants were a creature or a person. Do you believe that the Pants are really looking out for the girls? Or is what the girls sense a manifestation of their own emotions? Or is it some combination of the two?
10. Each of the girls is very different from her friends and has widely ranging talents: Lena is a painter, Tibby is a filmmaker, Bridget is an athlete. But their talents don’t define them so much as send them off in different directions. Carmen is more of an enigma; what would you say her talents are and where do they take her in the novel?
11. If you were given the Pants, what rule governing their use would be the hardest for you to keep? Rule 10 is “Remember: Pants = love. Love your pals. Love yourself” (p. 25). How is this rule observed by each member of the Sisterhood in the story? How is it broken?
12. In the epilogue (p. 293), Carmen says, “What happened in front of my friends felt real. What happened to me by myself felt partly dreamed, partly imagined, definitely shifted and warped by my own fears and wants.” Have you ever felt that way? How does it feel to see yourself reflected in other people?
13. The novel’s settings are varied—Baja California, Greece, South Carolina, and Maryland. By the end of the book, each of the girls has had a revelation that has a lot to do with where she has been. If you could spend a summer in one of these places, which would you choose? If you could spend a summer anywhere in the world, where would you go? Would you want your friends with you or would you rather travel solo?
14. What does Carmen mean when she says that she, Lena, Tibby, and Bridget are the real Septembers (p. 7)? What is it about their friendship that convinces Carmen they won’t drift apart the way their mothers did? Fast-forward ten years . . . do you think the Sisterhood will still be inseparable? What are the bonds that will help their friendship endure? Will the Pants still fit them? If not, will it matter?