1. Small towns like Calcasset, Maine, can be wonderful—Evvie has a strong support network, community traditions, stability—but there can also be downsides. After her husband’s death, Evvie keeps secret her previous plans to leave him. Why do you think she does this? Have you ever found it difficult to voice an ugly truth?
2. What does Dean’s unexpected and inexplicable inability to pitch a baseball mean to you? Have you ever found yourself in a situation where you haven’t been able to perform as you would like to?
3. Evvie and Dean are both thrown huge curve balls—Evvie loses her husband, Dean his livelihood. Do you think they handle the changes in their lives well?
4. Andy and Evvie are close friends with no romantic interest in each other—but things get complicated when Andy starts dating Monica. Have you ever had to balance a relationship and a close friendship?
5. Do you think that balance is further complicated if that friend is a member of the opposite sex? Is this an experience you can relate to?
6. As Evvie and Dean become closer, Evvie reveals more about her marriage. What does she come to understand about her marriage to Tim by the end of the book, and how does this new understanding change her?
7. Evvie finds it difficult to rely on others or to ask for help. Can you relate? Do you find it hard to depend on other people for emotional or practical support?
8. Why does Evvie decide to take a break from speaking to her mother? Do you think she makes the right decision?
9. Evvie, Andy, and Dean are all struggling with different forms of grief. What is each character grieving and how do they find ways to heal?
10. Why do you think Evvie puts off contacting Nona about her job proposition? Why do you think she finally does call Nona back? Have you ever put off an opportunity? What made you finally take the plunge?
Do you think Evvie successfully “starts over” by the end of the novel? How does she change from the beginning to the end of the book?
12. What actors would you cast in a film version of Evvie Drake Starts Over?