For a printable version of The Side Project book club questions click here.
- Rylee is torn between pursuing her dreams and caring for her brother. How does the novel portray this tension between ambition and obligation? Have you ever felt similarly torn between two paths?
- Carson and Rylee have very different memories of their high school relationship. What does this say about the subjectivity of memory in relationships? How does the past shape their present connection?
- The graduate writing class serves as a literal and symbolic space for reinvention. How do Rylee and Carson grow through their creative work—and how does fiction allow them to reveal truths they might not otherwise express?
- This book touches on themes of grief, especially through Rylee’s relationship with her late father. How does her father’s memory influence her decisions? What role do inherited dreams play in our lives?
- The “side project” starts as a no-strings arrangement. What makes this trope work so well here? Do you think either Rylee or Carson truly believed they could keep their emotions separate?
- Carson’s role as a single father adds depth to his character. How does this challenge typical romantic hero archetypes? In what ways does fatherhood shape his identity and his choices?
- There’s a meta-layer to the story, as characters write fiction within the novel. Did this element enhance your reading experience? What do you think Laurel Osterkamp is saying about the act of writing itself?
- How do setting and community shape the narrative? Would this story have worked the same way in a big city, or is the small-town environment essential to the plot and emotional tone?
- Both characters are vulnerable in different ways. What does the novel say about emotional bravery? Who do you think grows more over the course of the book—Rylee or Carson?
- If you were in a writing class with these characters, whose story would you want to read? Did the snippets of writing reveal more about them than their conversations did?