Helplessly Hoping follows Dale Matthews, a 70s rock star turned solo artist, whose fame, ego, and addictions collide with love, responsibility, and the ghosts of his past. When his efficient but guarded assistant Nicki Barrons enters his life, a complicated relationship unfolds against the backdrop of fame, desire, and the challenges of adulthood. With themes of identity, addiction, love, and the cost of success, this novel makes for a raw and emotional book club discussion.
Discussion Questions
- Dale begins the novel confident in his rock star persona but conflicted in his personal life. How did you see him evolve—or resist change—through the course of the story?
- Nicki is introduced as distant and professional. How does her presence challenge Dale, both personally and professionally?
- The book weaves in postpartum depression, addiction, and strained relationships. Which of these struggles resonated most strongly with you, and why?
- The story explores the tension between personal happiness and professional success. Do you think Dale can ever have both?
- How did secondary characters like Dale’s bandmates, exes, and old friends shape the pressures Dale and Nicki faced?
- How did the novel portray Nicki’s struggle with postpartum depression? Did it give you clarity into her experience?
- In what ways did Nicki’s independence conflict with or support her relationship with Dale?
- Looking back, what moments made you most connect with Nicki as a character?
- If Helplessly Hoping were adapted into a film or limited series, who would you cast as Dale and Nicki?
Enhance Your Book Club Night
- Curate a playlist of 70s rock anthems and deep cuts (Crosby, Stills & Nash, Eagles, Fleetwood Mac, America or check out my Spotify Helplessly Hoping playlist curated specifically for my novel).
- Pair with wine, cocktails, or comfort food that feels at home in a backstage greenroom.
- Share your reflections with me on Instagram (@heatherjbennett_original) — I’d love to see your book club in action!
Invite the Author
Want to bring the conversation to life? I’d love to join your book club meeting — either in person (if you’re local to the Dallas/Fort Worth area) or virtually via Zoom. We can talk about the writing process, the 70s rock inspiration behind Helplessly Hoping, and answer any questions you have about Dale, Nicki, and the world of the book.
To set up a visit, just fill out the form on my Linktree and I’ll get back to you!
