Damon is faced with a new reality without the love of his life; Bonnie decides to be Damon's moral compass, and look out for Alaric, who lost his fiancée. Stefan protects the town from Lily; Enzo must decide who he is loyal to.

Damon makes a decision that could ruin Lily and Stefan's deal; Alaric needs Bonnie's help with an artifact; Caroline discovers a shocking secret.

Just as Damon thinks he's gained the upper hand in his fight against Lily, an unexpected turn of events leaves him scrambling for a plan B.

Bonnie, Damon, and Alaric go through a tough shock with the Phoenix stone, while Caroline sent Stefan to spend the day with his ex, Valerie.

Damon and Stefan conspire to kill Julian, while Caroline struggles with the fact that she's pregnant with Ric's kids.

It's Nora and Mary Louise's anniversary and Julian has big plans for the night, however, Lily and her sons have even bigger plans for Julian.

In the events following their mother's passing, Stefan and Damon try to engage in the holiday spirit.

Damon's soul is stuck in the phoenix stone, the world of the phoenix stone is trying to break Damon emotionally and at the same time Damon's family and friends are trying to bring him back.

Caroline throws a baby shower for Alaric's twins, and the Salvatore brothers face the hallucinations caused by the Phoenix Stone.

Stefan uncovers the reason behind Damon's dark descent following his experience in the Phoenix stone.

Vampire hunter Rayna Cruz is on the loose and Damon has to make things right when his actions inadvertently put his loved ones in her path.

Stefan goes to New Orleans to lure Rayna Cruz away from his friends and comes face to face with Klaus Mikaelson, who's suspicious of his old friend's arrival.

Tired of having everyone sacrifice themselves for him, Damon decides to leave the group. Meanwhile, Bonnie's new discovery threatens Damon's plans to stop Rayna.

Stefan will find himself with a choice to make and his decision will determine the fates of everyone he cares about, especially Damon.