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It is the end of the summer and Elena (Nina Dobrev) and Caroline (Candice Accola) need to get ready for college.Though a bit hesitant, Damon (Ian Somerhalder) says his goodbyes to Elena as she leaves for Whitmore College since neither of them wants to leave each other after their newly started relationship.
On the Damon/Elena chemistry she wrote, "Surprisingly, the scenes between Damon and Elena were a lot more interesting and sizzling than one would expect. The kitchen scene where he tells Elena about Katherine was more poignant, especially after Elena softly told Damon: "I'm sorry" and when he looks back at her puzzled, she explained ...
Damon does not want to let Elena out of his sight, so Elena asks Stefan's help. Stefan snaps Damon's neck and Elena meets Esther. Esther explains to Elena why she is not dead even though Klaus killed her many years ago. She also tells Elena her plan and that the real reason she wanted all her children together was to link them as one so she ...
After Damon and Elena's long lives shared together, Elena finds peace in the afterlife and reunites with her parents, John (David Anders), and Jenna (Sara Canning); and Stefan, at peace, opens the door to the boarding house to see Damon, who greets him with "Hello, brother" in a nod to the words Damon first said to Stefan in the pilot episode ...
The episode starts with a scene from 1864 where Katherine (Nina Dobrev) and Stefan (Paul Wesley) dance at the Founder's party. While they are dancing, Stefan sees that Damon (Ian Somerhalder) talks with Elena and they leave together. He runs after them and the scene jumps to the present where Elena is now playing pool with Damon. Katherine ...
Elena almost gets Damon to make out with her again, but they are interrupted by a phone call. Bonnie tells Elena they need to meet because she is teaching Jeremy to control his vampire hunter urges. Meanwhile, Elena and Damon go to the Gilbert Lake House to help Jeremy face some dangerous inner demons.
Elena runs to the tomb but Damon follows her and stops her before she gets in. Elena leaves and Stefan makes Damon promise him that he'll protect her and keep her away from the tomb. Damon promises and leaves and Katherine points out to Stefan that this was the biggest mistake of his life.
Katherine (Nina Dobrev) calls Damon (Ian Somerhalder) and tells him that she knows where Stefan (Paul Wesley) and Klaus (Joseph Morgan) are. Damon gets Elena and go to Chicago to find Stefan. At Chicago, Damon takes Elena to Stefan's old apartment and shows her all the names of Stefan's victims back in the 1920s when he was "The Ripper".