The first volume of the series introduces the reader to Elena Gilbert, a popular high school student in Fell's Church, Virginia, and her best friends Bonnie, Meredith, and Matt. A former friend, Caroline, is also introduced and revealed to be Elena's antagonist. As her senior year at Robert E. Lee High School begins, Elena meets and becomes involved with a mysterious new student, Stefan Salvatore. At the Homecoming dance, Elena is upset to see that Caroline showed up with Stefan, and later leaves with Dick, Tyler, and Vickie to go to the cemetery. After getting Elena alone with him in the graveyard, Tyler tries to rape her, but she is rescued and brought home by Stefan. As Elena and Stefan fall in love, strange attacks begin to happen in the town, and Elena encounters another mysterious man - Damon, who turns out to be Stefan's older brother. During a Halloween fundraiser at the high school, Bonnie finds their history teacher, Mr. Tanner, dead. When Elena leaves to go to the boarding house where Stefan is staying, she finds him on the roof, feeding on a dove. She starts to back away in fear and falls from the roof, but he catches her and then they both go back up to his room. Stefan reveals his past, and explains that he wasn't avoiding her but protecting her. After Stefan takes Elena home, Damon shows up to taunt Stefan with his own desire for Elena. This leads to a vicious fight. In the morning, Elena becomes upset that Stefan is missing.
The second book picks up where The Awakening left off and delves further into Damon's attempts to win Elena's affections and Stefan's struggle to survive. Elena summons Damon and confronts him in the graveyard to discover Stefan's whereabouts. Damon claims he killed Stefan the previous night, but Bonnie, a witch, has a psychic vision. When they find him at the bottom of the empty well, Stefan is close to death, but Elena saves him by forcing him to drink her blood. Elena also strikes a secret deal by exchanging blood with Damon, and by doing so ties herself to both brothers as Katherine did centuries ago. While waiting for Stefan one night, Elena feels as if something is coming for her, and she frantically tries to escape by crossing the bridge over a river. The car she is in veers off the road and into the river, and she drowns. She fights to get up from the water but stays in the water long enough to die. Meanwhile, Stefan, Meredith and Bonnie are all looking for Elena. They find her shortly after the car veers off the road and Stefan dives in to save her. He drags her body out of the water but it is too late, Elena is dead. He then tells Meredith and Bonnie to go to the police while he, angry and grieving, tries to find and kill his brother. The Struggle ends with the revelation that, because she took enough of the brothers’ blood, Elena becomes a vampire upon her death.
The book deals with Elena's adjustment to her vampirism, as well as her confusion over feelings for both brothers. Stefan believes and knows that Damon was the force chasing Elena. They were fighting, in the middle of the time Elena awakens and attacks Stefan as, Elena viewed Stefan as a threat and the brothers stop the fight. Stefan, heartbroken, assumes that her attack meant she loved Damon more, and Damon attempts to clear everything up. After Elena has fed, Damon hides her. Once rested, she begins to realise how she treated Stefan when the brothers were fighting and deeply regrets attacking him and decides to wander in the woods. She ends up at the church where a memorial is taking place. She decides to wait in the attic of the church for Damon to come and find her. Something begins to dawn on her as she waits in the attic. She can see her friends and family in the church and people are talking about her. It is her memorial and the whole town has gathered to remember her. Stefan and Damon are alerted by Elena's distress and rush to her side. Stefan arrives first and when Elena sees him, she realizes further that she loves Stefan more than she loves Damon. Damon arrives as the service ends and Stefan and Damon are soon bickering. They are interrupted by a pack of dogs attacking townspeople outside the church. Elena, Stefan and Damon conclude that the force that made Elena's car drive off the bridge was controlling the dogs. Their suspicions were proven correct, as it turned out that the person responsible for Elena's death and all of the strange events in Fell's Church was Katherine, as Elena, Stefan, Damon, Bonnie, Matt and Meredith find out as they enter the crypt where the founders of Fell's Church are burried, and where Katherine has been hiding. Everyone but the three vampires escape to help the town which comes under siedge by dogs controlled by Katherine. Katherine was furious at the Salvatores for killing each other before when she had faked her death so they would re-connect, when this just made them grow even more appart. She also gets furious