Rebekah has arrived, and she does not disappoint. We flash back to the 1920's, where we learn about Stefan's Ripper days in Chicago, and how he was entangled with Klaus and Rebekah at the time. In the present day, Klaus undaggers his sister in order to get info from a very old, yet very young, witch named Gloria. That doesn't go so well since Katherine kills her. And everything leads back to Elena, as usual, because what they need is the necklace that Stefan gave her, which used to be Rebekah's.
Back in Mystic Falls, Caroline is being put through some form of conversion therapy by her vampire hating father, and that goes as well as other forms of conversion therapy do. Luckily, Tyler and Liz save her. Meanwhile, Jeremy spills the beans about his Ghosts of Girlfriends Past to Bonnie, and shuts Anna out in the process. And Alaric claims a spot on the Council in the place of the missing Gilbert quotient because someone has to protect the humans now that Liz and Carol are compromised by their children's new supernatural classifications.