Oleg Sapoundjieva

Elena puts herself in a dangerous position as she searches for the truth about Katherine's past and what her own future may hold. Knowing that Stefan would never agree to her plan, Elena swears Caroline to secrecy. Damon uses a newfound confidant to help him try to discover the real purpose and power of the moonstone. Jeremy and Bonnie meet Luka Martin (guest star Bryton James – The Young and the Restless, Family Matters), a new student with a surprising family history.

When Enzo (recurring guest star Michael Malarkey) brings Damon a gruesome present and insists that they bond by committing an act of revenge, Damon makes an effort to do the honorable thing. After finding himself in awkward and confusing conversations with Nadia (recurring guest star Olga Fonda), Matt impulsively decides to throw a party, where Caroline makes a stunning confession to Elena, then has to face the consequence of her actions with Stefan and Tyler. Aaron (recurring guest star Shaun Sipos) does his best to make amends for his family’s past misdeeds and start a new life for himself. Finally, Elena suddenly finds herself in a life-threatening situation with only minutes to figure out how to save herself.

As she faces a new crisis, Katherine remembers the traumatic night in 1490 when she gave birth to the daughter who was immediately taken from her. Stefan lets Elena, Caroline and Bonnie know that Katherine’s health has taken a turn for the worse, while Damon, Matt and Jeremy discuss some of Katherine’s most notorious moments. Nadia (recurring guest star Olga Fonda) comes up with a frightening plan to protect her mother, and Stefan and Elena are forced to help her. Meanwhile, Caroline is mortified when she realizes she forgot to fill Elena in on the latest shocking gossip, then indulges in a little scandalous behavior of her own. Finally, Elena and Katherine share an unexpected moment of connection.