Spoiled billionaire playboy Oliver Queen is missing and presumed dead when his yacht is lost at sea. He returns five years later a changed man, determined to clean up the city as a hooded vigilante armed with a bow.

As a means to distract herself from an affair, a love-addicted woman befriends a cleaning lady, badly scarred by burns. She soon learns, these scars run much deeper than the surface.

This takes place several years before Cruel Intentions (1999), back to when Kathryn first meets Sebastian, their sexual attraction to each other and their enjoyment in destroying the lives of their peers.