1. Chase and Maisy’s relationship begins with a bit of conflict. How do their first impressions of each other shape (or mislead) their understanding of one another throughout the novel?

2. Chase insists that his mother’s death doesn’t affect him, yet his actions suggest otherwise. How does the novel explore unresolved grief? What ultimately allows Chase to begin healing?

3. Maisy challenges Chase to “pay it forward.” How does this simple idea transform him? Which of his acts of generosity feels most meaningful to you --- and why?

4. Family plays a central role in this story --- from Maisy’s close-knit household to Chase’s emotionally distant upbringing. How do their different family experiences shape their views on love and commitment?

5. Chase initially equates strength with control and independence. How does his understanding of vulnerability evolve? What moments mark a turning point for him?

6. Maisy’s mother and grandmother consistently express faith that “God will provide.” How does faith influence the characters’ decisions and perspectives during times of crisis?

7. Michelle’s story (Chase’s mother) reveals redemption later in life. How does her journey parallel or influence Chase’s own transformation?

8. Maisy struggles with her belief that love alone isn’t enough. What does the novel ultimately suggest about love versus practicality?

9. Several side characters experience change because of Chase and Maisy’s influence. Which secondary character’s arc resonated most with you?

10. If you could ask Debbie Macomber one thing about CHASING THE CLOUDS AWAY, what would it be?