1. Grace and Andrew are convinced their plan is the best plan. Have you ever felt that your partners’ goals clashed with your own?
  2. Fear is powerful and can motivate us or keep us stuck. How has it motivated you or kept you stuck?
  3. Andrew surprises Grace with his cooking skills. Have you ever had a date/partner cook a meal that impresses you?
  4. Grief affects us all. Discuss how grief and loss impacts Grace and her decisions. Can you relate? Do you think you’d have acted differently?
  5. Grace is a strong woman but still has let other people shape her life. Do you have any similar contradictions in your life?
  6. Why do you think Grace believes her only way forward is alone?
  7. Grace struggles with their age difference. How has our culture has shaped her thoughts on this issue? Why is there a word for women who date/marry younger men (cougar), but not a similar word for men?
  8. Andrew has a complicated relationship with his father – one that likely could have been easier with a single conversation. In retrospect, have you ever thought, “If only I’d said/explained/shared X everything would be different?”
  9. In your opinion, was Jax a good guy or a bad guy?
  10. After such a big loss, would you be able to move forward and love again?
  11. Was Grace right to give into Ford’s ultimatum?
  12. Grace tells Andrew that after loss you “move forward” you don’t “move on.” Do you agree? Why or why not?
  13. Coffee is mentioned over 100 times in the book. Do you have a food or drink that is a constant in your life?
  14. Music is vital to both Grace and Andrew – it feeds their souls. What role does music play in your life?
  15. This book is all about second chances. Discuss where this theme shows up and with what characters. Do you believe in second chances?
  16. At the beginning of the book, Grace is dealing with writer’s block. What piece of advice would you give someone in your life if they were blocked – on a work matter or a personal matter?
  17. This book is set in multiple locations. If you could visit one setting, which one would you choose? And which character would you choose to travel with?
  18. Grace and Annie have a very tight friendship. Discuss what role friendship plays in your life.
  19. What do you think will come next for Grace and Andrew?
  20. Families come in all shapes and sizes. Grace has a strong relationship with her family (shown in the novella, Friday at the Blue Note), but also relies heavily on found family (Annie, Will, Curtis). How do you define family?