1. Is what Isaac did to Stephanie justified considering her past behavior with men? Why or why not?
2. Should Keith have warned Stephanie about Isaac?
3. There is a reoccurring theme in the Gibbons Gold Digger series of influential father figures: Lauren Gibbons saw Chef Phillip Rochon as her father figure in book 1 (Can’t Stand the Heat), and Mike Stokowski serves as a father figure for Keith in book 2 (The Player & the Game). What role do these men serve for both the characters and plots in the series?
4. Dawn says one of her biggest issues with her nemesis, Sasha, is Sasha’s hypocrisy about her own past promiscuity, and using her body to make her way to the top. Dawn says she has run into many women who are hypocritical like Sasha. Do you think there are more “down low” gold diggers out there than people would like to believe?
5. Myra Beaumont taught Isaac everything he knows about running cons. Is she right to feel angry when he betrays her, or should she have known there’s no honor among thieves?
6. After Keith and Stephanie have sex, he treats her coldly. Are his feelings and behavior toward her justified?
7. Dawn is reluctant to engage in a tryst with the artist, Razor. Is it just the family rules holding her back or is it something else?
8. Keith tells Stephanie that she behaves like a prostitute. She says that he’s just as small minded as the people in Chesterton who unjustly judge her and her family. Is she right?
9. Stephanie decides in the end to take a chance and build a relationship with Keith. Is Dawn right that Stephanie is being naive about the couple’s future considering Stephanie’s past preference for rich, powerful men?
10. Stephanie finally gets a chance to confront Isaac and tells his new lover, Manny, the truth about his past. But Manny ignores her warnings. Was it true love or blind ego that influences Manny’s decision?