Damon and Alaric reluctantly go along with Elena's new strategy to find Stefan, leading Damon into a dangerous fight with an unexpected enemy.

Klaus takes Stefan to Chicago, where he wants to resuscitate his sister Rebekah, who might hold the key to breaking the curse. Gradually, Stefan is reminded of his Prohibition period affair with her while still bloodthirsty himself, and its tragic end. Tyler is rightly worried, turning for an ally to her mother sheriff Forbes, about the whereabouts of Caroline, whose bully father Bill actually holds her in a dungeon for 'vampire aversion therapy' of the most flagrant kind. Katherine puts Damon on feared Klaus's trail, so he can mount a rescue with Elena after putting her in her place.

In Chicago, Katherine meets Stefan in front of a store and she tells that Elena has the necklace that belongs to Rebekah. She also feels that Stefan is plotting a scheme against Klaus, but he does not share his plan with her. Meanwhile, in Mystic Falls, Anna shows up to Jeremy and talks to him that she is alone in the afterlife. Gloria seeks out the necklace using a spell while Bonnie and Caroline visit Elena; out of the blue, her necklace burns her chest. Damon is upset with people trying to change him to be Mr. Nice Guy. Sheriff Forbes asks him to compel Bill to forget everything but Bill resists. When Damon decides to kill Bill, Caroline protects her father. Meanwhile Gloria tortures Stefan to discover who is wearing the necklace but Katherine unexpectedly kills the witch. Stefan discovers that Klaus fears a vampire hunter, Mikael, and tries to get more information from Rebekah. She's suspicious of his attitude and tells this to Klaus, who decides to return to Mystic Falls.

Prophetic dreams about the mysterious fourth coffin lead Bonnie and Elena to a surprising source, while Tyler seeks help to break free from Klaus' bond so he can be with Caroline. Alaric's new friend Dr. Fell has a secret no one sees coming, and Stefan's interference in Elena's life reveals something that surprises even him.

Now Klaus has Elijah back, they host a dinner party to negotiate a future with the Salvatore brothers, who actually procrastinate. Meanwhile combined witchcraft finally opens the mystery coffin, from which a scary surprise guest is released, but both families will be shocked. Alaric has been wounded dangerously by lover Dr. Fell, who happens to be supernatural, which makes saving him problematic, but Elena steps up. Caroline's father Bill Forbes refuses to survive his vampire bite by allowing Caroline to turn him into one like her.

The present-day murders in Mystic Falls remind Damon of a similar crime spree a century earlier. Flashing back to 1912, Damon recalls a beautiful vampire.