1. Why do you think this novel is entitled The Big Beautiful? What do you think “the big beautiful” refers to?
2. Do you think one can be too old for romance? If you were Doris’s age, with her health, would you be open to a new courtship? Is it her self-consciousness about her illness or something else that holds her back?
3. Each month starts with a literary quote about love. How do the quotes connect to what happens in the section of the story that follows?
4. There are three generations in this novel. Are they different in how they perceive love? What are the similarities that tie the many different characters together?
5. Evelyn sums up the novel as being about late bloomers and second chances. How is this theme reflected in the characters, and their relationships with each other and their town? In the landscape of their town?
6. Cassandra and May both say they wouldn’t give anything to go back in time. Cassandra is happy she is past Annie Laurie’s age and May is happy she is past Cassandra’s age. Would you go back to a certain age if you could? If so, what age and why?
7. What role do you think the ocean plays in relation to the characters? Is it seen as friend or foe? Doris hates it. The rest of the O’Neal family would never want to be away from it. Do you think the ocean is a strong character in this novel?
8. Annie Laurie twice almost drowned in the ocean, first as a little girl and then on the boat with Dennis and Hector. What did she learn from those two experiences? What does the ocean represent to her?
9. Throughout the novel Cassandra references romance novels and movies. Do you think Cassandra is too wrapped up in the ideal? Does this help her to see what she wants? Are men as susceptible to the allure of romance as women?
10. Cassandra gets close with Annie Laurie. Do you think Cassandra was responsible in pursuing this friendship knowing she was leaving in a few months? Do you think Doris was right in lecturing Cassandra about her relationship?
11. Why do you think Cassandra is so drawn to Hector? Why does she keep dating Dennis? Did she rush too quickly from one man to another? Would she have been better off taking more time for herself?
12. All of the characters want love. And they all run from it. Cassandra avoids Hector. Annie Laurie avoids Jim. Evelyn avoids her family. Why do you think this is?
13. Would you rather have love or romance? Are the two separate as May says? Can romance have different definitions for different people, just as love does?
14. Why do you think Dennis changes his life? Does he do it for Cassandra or for himself? Do you think it is good to change for love? How do Dennis and Cassandra act as catalysts in each other’s lives?
15. Do you think Cassandra is Hector’s hero or Hector is Cassandra’s hero? If so, what are they saving each other from? Is it possible to be your own hero, or do you need relationships?
16. It is said that geographical cures don’t really work because no matter where you go, there you are. How does this theory play out in Cassandra’s story?
17. What does the story say about different definitions of motherhood? Of family?