1. Trisha Portman is serious about herself, her work, and her relationships. How does this seriousness play itself out in contradictory ways? In what ways do you find her typical of many young women today?

2. The friendship between Nat and Trisha seems an unlikely alliance. What makes it work?

3. Trisha has a list of attributes she's looking for in a man: someone who's artistic, kind, and passionate about something. She says she's "flexible on looks." Is she really? Where do Trish's ideals lead her?

4. James Morales is a complex character. Is he a demon or damaged goods? How does your opinion about him change? What are some of his redeeming traits?

5. The lives of Trisha and James keep intersecting at important moments. At what point do you think Trisha might be starting to care about James? Yet why do Trisha and James keep repelling each other?

6. One theme of the story is the tyranny of the superficial. Once Trisha realizes that she's dying of cancer, she sees James completely differently. Do you think it takes something that extreme to empathize with someone like James?

7. How do you feel about James's rejection of his art? Do you think he should have exploited his ability? Does his past justify the brutality with which he rejects his talent?

8. After Trisha is ill, she asks James for help, including shaving her head once her hair starts falling out. Finally, she demands that he paint her portrait. What is the significance of that collaboration? How does it explain the beginning of the book? Do you think that Trisha is in agony or ecstasy?

9. What do you think happens at the very end? Is Trisha hallucinating? Does James give her the drugs? Do you think suicide is a reasonable solution to Trisha's and James's problems?

10. The author, Stephanie Williams, died of breast cancer at the age of 33, weeks after this books was published. Although Enter Sandman is a work of fiction, she was experiencing the ravages of cancer while she wrote this book. Does knowing the plight of the author enhance the reading of this novel?

11. An important theme of this novel is the idea of leaving something behind after you die. If you knew you had a short time to live, what would you want to leave behind?