Taylor Treadwell

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.

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.

Ray is in recovery mode, striving to reconnect with his family and repair his relationship with Bridget. As he tries to reconcile past trauma with the guidance of Father Romero, he finds a professional boxer and fellow abuse survivor in need of his assistance. Bunchy and Teresa face impending parenthood together as Abby receives a medical diagnosis that threatens to upend the Donovan family. In the aftermath of the Minassian shootout, Ray becomes embroiled with an enigmatic art dealer who has ties to the Russian Mob. Hiding out in Primm, Nevada, Mickey plots a heist against a formidable casino owner as Detective Muncie closes in on his trail.