The fifth book starts with Elena’s return from the dead. She returns from the afterlife with super human powers which makes her blood irresistible to vampires. Stefan is determined to keep Elena safe and wants to leave Fells Church, though in the end he does not. Damon, being the power hungry vampire that he is, wants Elena to stay with him and rule as his princess of the dark. Damon struck a deal with a new vampire in town, Shinichi—he would take care of Stefan, but in return, Shinichi would take over Fell’s Church. When Stefan is lured away from Fell’s Church, he tries to convince Elena that he is the brother that she should be with. Damon, always the hunter, is now the hunted when he becomes the prey to an evil insect that can possess anyone, and it desires not just Elena’s blood, but also her death. Damon watched Elena’s friends (Matt, Bonnie & Merideth) almost die, but he later on regained control. In particular, Bonnie was on the verge of death before Damon saved her, showing that he does care for humans, and that he has feelings for her, though he continually shows his love for Elena still. Afterward, Stefan mysteriously disappears, leaving a note in Elena’s diary, which Damon deleted, instead saying that he left her for her own protection when the real note was to warn her that if he was to disappear, it was Damon to blame—he wanted to become a human again after Damon gave him a website address that was for Shi no Shi, meaning ‘death of death’, advertising a way for vampires to become humans again. As the town becomes infected by these evil creatures that possess humans, Matt is wanted for arrest, and Damon lapses in and out of control over his own body.
There are many new characters introduced, such as the Saitous, a Japanese family, consisting of Isobel, who becomes possessed by the evil creatures, her little brother, and her grandmother, Obaasan, who was a shrine keeper once. Ms. Flowers is now revealed to be more than a batty old woman—she is in fact a powerful white witch who knew all along that Stefan was a vampire. The new villains in town are kitsune (fox demons) named Shinichi and Misao, Japanese twins, who came to Fell’s Church because they were attracted to its evil aura. It is revealed that even after all this time, Matt continues to have feelings for Elena.
In the end, Damon gains control of his body, and Elena helps him remember everything he has done by removing the insect from his body. Damon is disgusted with himself, but he and Elena manage to subdue the twins, though they will return to Fell’s Church. Matt, Elena and Damon set out to find where Shinichi has hidden Stefan—both men are attracted to her, though she is trying her best to resist Damon, she remembers her past with Matt.