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.

In the aftermath of a clever plan orchestrated by Lily, Damon sets off on a road trip with Bonnie and Alaric in search of leverage they can use against his mother. Meanwhile, Caroline, who is being held hostage by the Heretics, learns some shocking information about Valerie's past, while Stefan learns a few unexpected details about his own past from Lily. Finally, Alaric turns to Bonnie for her help after coming clean about a secret he's been keeping.

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.

After being reunited with her former love Julian, Lily hosts a dinner party to introduce him to Damon and Stefan and to declare peace between her family of Heretics and the residents of Mystic Falls. Damon and Stefan find themselves at an impasse when they realize they have differing views on how to handle Julian's arrival.

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.

In the aftermath of his brother's fateful decision, Stefan awakens to find himself thrown into a life or death situation with only his basic instincts to rely on. With time working against him, he sets off on a journey of survival while forced to confront a lifetime of irreversible damage Damon has done to their relationship.

Determined to capture an escaped vampire named Ambrose, who may be the key to getting Stefan back safely, Damon heads to Memphis with Alaric in tow. However, reluctant to step back into his former vampire-hunting ways, Alaric makes his unwillingness to participate clear, while revealing the truth about the past three years of his life without Damon.

When Enzo's efforts to protect Bonnie end up putting her life in jeopardy, they learn that Rayna may hold the key to her survival. With time running out and Rayna at the reins, Enzo and Bonnie reluctantly team up with Damon, who is desperate to save Bonnie's life and to repair their broken friendship.

With Bonnie's life at stake and an uphill battle ahead of them, Damon and Enzo lead the charge to save Bonnie before her condition worsens. Stefan reluctantly teams up with Matt for the sake of Bonnie and uncovers the truth behind Matt's anger towards him.

When Damon's risky attempt to save Bonnie takes an unexpected turn, the consequences of his actions forces everyone to band together to help her pull through. Meanwhile, when a new threat leaves Caroline's life in jeopardy, Stefan makes a rash decision that ultimately forces them to face the fallout from their relationship.

Despite their best efforts to help Bonnie through the harrowing predicament she now faces, Damon, Enzo and Caroline realize their options are running out and drastic measures need to be taken. With their only chance of saving their friend lying inside the Armory, Stefan breaks the news to Caroline that they may need help from an unlikely source. Matt cries again and leaves, if only that was the end...