Sia Sapoundjieva

Elena gets herself into danger as she searches for more information about Katherine's past and her own potential future. She recruits Caroline to help her, knowing that Stefan would never agree to her plan. Elsewhere, Damon uses a new confidant to aid him in uncovering the real purpose and power of the moonstone, and Jeremy and Bonnie meet a new student with a surprising family history.

Enzo brings Damon a gruesome present and insists that they bond by committing an act of revenge. After finding himself in awkward and confusing conversations with Nadia, Matt impulsively decides to throw a party, where Caroline makes a shocking confession to Elena.

Stefan lets Elena, Caroline and Bonnie know that Katherine's health has taken a turn for the worse, leading Nadia to come up with a frightening plan to protect her mother. Damon, Matt and Jeremy discuss some of Katherine's most notorious moments.