As season five begins, Damon and Elena have spent a blissful summer in love, unaware that Silas is free and Stefan has been suffering agonizing pain every day for months. Damon believes Stefan is staying away because it would be too painful for him to see Damon and Elena as a couple, but Elena can’t escape the uneasy feeling that Stefan needs their help.
While Elena is reluctant to leave Damon and Jeremy, she is also thrilled to be heading off to a new start at nearby Whitmore College with Caroline as her roommate. Still unaware that Bonnie is dead, Elena and Caroline are waiting for their friend to join them at college. Jeremy is the only one who can see and talk to Bonnie who is trapped on the Other Side.
Caroline is also waiting impatiently for Tyler to return and join her at Whitmore. Matt and Rebekah have spent a wonderful summer traveling through Europe, and the newly cured Katherine is having a tough time adjusting to being human after 500 years as a vampire. Returning to town after months on the run, Katherine asks Damon to help her now that she is vulnerable to her many enemies. Although everyone in this tight-knit group of friends is trying to move on to a new and better phase of their lives, the past is always with them, and Silas is determined to use his powers and the secrets of dopplegangers to make sure no one remains unscathed.