1. Love Finds You in Holiday, Florida is a comedy. But underneath the laughter, what is the overall theme of the book?

2. Cassie has very definite roles within her various relationships. What are the contrasts between Cassie’s longtime role with Zan and her new role with Richard?

3. Cassie initially finds Richard somewhat irritating. Why do you think she is so resistant to Richard?

4. Does a person’s role within a marriage define who they are as a person? If so, why? And in what ways?

5. The story opens with Cassie reacting to Zan placing two plastic pink flamingos in their front yard. What do those silly flamingos represent in this story?

6. Richard’s behavior is often scrutinized and misunderstood. How did you feel about the misconceptions people had about Richard’s intentions?

7. Every chapter of the book begins with a crossword puzzle clue. What do those clues represent?

8. Have you ever felt as if you were defined by certain adjectives (i.e., stubborn, nurturing, beautiful)? If so, do you feel the pressure to live up to those definitions?

9. How did you feel about the Surprise Yourself scripture cards? What do you think Cassie learned from them?

10. In the context of her relationship with Millicent, how did Cassie change during her time in Holiday?

11. How did Cassie’s relationship with the Lord develop over the course of the story?

12. What did Zan’s dog Sophie represent throughout the book?

13. What similarities can be drawn between the refurbishing of the Holiday house and Cassie’s journey?

14. When the story concluded, what were your feelings about where this couple was headed? Where do you see them in five years?