Do you prefer breakup songs or love songs? Why?
While Riley is living out her dreams, she faces stress, insecurity, and loneliness. Do you sympathize with her struggles and the price of stardom?
Max closely associates memories with songs. Do you experience this as well? Why does music endure over our lifetime?
Until the end of the novel, Riley believes her best art comes from her pain. Do you think this is true of other artists? Do we as a society look upon art about suffering as somehow deeper or more meaningful than art about joy?
Max chooses family over trying out a dream he doesn’t know if he wants. Was it the right choice?
Which musicians do you think served as inspiration for the character of Riley Wynn? Do you think they feel similar expectations and pressures as Riley in the book?
Do couples need to have a common dream—not necessarily professional, but something beyond love and attraction—that puts them on the same path in life?
Riley is criticized for writing about her ex-boyfriends. While Max is uncomfortable with it at times, he always recognizes that it is her prerogative to write about her own life. Do you agree?
How do you think the journey of self-discovery of Riley’s mom, Carrie, on the tour affects Riley’s growth? Did you like their mother-daughter relationship?
Riley believes in taking inspiration from her heartache because in some ways it gives purpose to her pain, like turning lemons into lemonade. Do you agree this is something we should always try to do?