A century after their first encounter, Damon and Sage meet again at the ceremony to kick-off the restoration of Wickery Bridge. Damon is surprised to learn the reason Sage has returned, and pleased when she devises an unusual method to help him figure out what Rebekah is up to. Abby is having a hard time adjusting to her new reality, despite Bonnie and Caroline’s efforts to help. When Damon informs Elena of Stefan’s latest struggles, she reaches out to Stefan to help her save a friend in danger, in hopes that it will help bring Stefan even closer to his humanity. Finally, when Damon discovers a new secret weapon, he lets Stefan in on the news.

Connor continues his search to uncover the secrets of Mystic Falls and tries to convince Jeremy to work with him. With Dr. Fell’s help, Damon and Klaus question Connor, but the confrontation takes a lethal turn. Trying to keep her new life as normal as possible, Elena is determined to continue her senior year at Mystic Falls High with support from Matt and Caroline. Rebekah’s arrival at school makes it difficult for Elena to control her anger, but she learns that confronting Rebekah can be extremely dangerous. Later, Rebekah realizes how alone she is, and reaches out to April. Stefan takes Elena on a thrilling motorcycle ride in an effort to show her that life can still be fun. Tyler gets a surprise visit from Hayley, a werewolf who helped him through the ordeal of breaking his sire-bond to Klaus. Concerned about Elena, as well as his own emotions, Stefan turns to a sympathetic Caroline for advice.

When Stefan arrives back in Mystic Falls with Elena and Jeremy, Caroline is immediately worried about Elena’s state of mind. Stefan reaches out to Dr. Fell and Matt for help. Still on the island, Damon relays somber news to Rebekah, and is surprised at her reaction. Together, Damon and Rebekah learn an unexpected bit of recent history from Vaughn. Everyone is horrified when Bonnie reveals the rest of Shane’s plan. Finally, after Damon does his best to help her, Elena comes up with a plan of her own.

As the fifth season opens, Elena, after a passionate summer with Damon, heads to college nearby with Caroline as her roommate. Plus, a terrifying appearance by Silas.

Nadia recalls her centuries-long search for her mother. Stefan, Caroline and Matt come up with a desperate plan to save Elena's life. Damon baits Tyler into an ugly confrontation and seeks revenge against Dr. Wes. Bonnie learns a terrifying secret that threatens the lives of all her friends.