Damon is trapped by Dr. Wes, and realizes scary things about his past.

Damon realizes Elena is in danger and enlists Stefan's help to find her. The brothers pay a visit to Aaron, and Damon shocks Stefan by revealing his first-hand knowledge of Aaron's family. In an attempt to stop Damon, Dr. Wes unleashes his secret weapon, forcing Damon to deal with a part of his past he thought was gone forever, as well as the consequences of his decades-long plan for revenge. Meanwhile, Elena is horrified by Dr. Wes' confessions about the dark history of Whitmore College and his own ultimate goal. Finally, a frantic Katherine turns to Matt for help, until she realizes that Nadia may be the one who can solve her problem.

Damon tries to get back together with Elena, however, Katherine has a plan and attempts to take Elena's body permanently. Tyler is upset with Caroline and Matt is used by Katherine. Enzo finds Damon and they decide to become a team again.

Hoping to help everyone move past recent traumatic events, Caroline convinces Elena and Bonnie to attend Whitmore College's "Bitter Ball" for broken-hearted students. Bonnie is intrigued with a fellow student named Liv, who appears to be dabbling in witchcraft. Tyler starts to worry about Matt's relationship with Nadia. After making a disturbing discovery, Stefan has a frustrating conversation with Damon and Enzo. Dr. Wes struggles to continue his research project with help from a new benefactor named Sloan. Still bent on revenge, Damon and Enzo resort to violence to convince Bonnie and Jeremy to help them, but their plan takes an unexpected and horrifying turn.

As Damon's behavior escalates from destructive to deadly, Stefan begins to regret their last conversation and decides to track Damon down and intervene. For reasons of her own, "Elena" volunteers to come along. Dr. Wes enlists the Travelers to set a trap that will once again test Damon's friendship with Enzo. After a heart-to-heart talk with Nadia, Matt enlists Caroline and Tyler's help to protect Elena, leading to a violent confrontation. Later, when Stefan tries to comfort a dejected Caroline, their conversation leads to a horrifying realization.

Damon tries to figure out how to make a disturbing confession to Elena.

Bonnie has an unsettling encounter with Luke (CHRIS BROCHU), and learns more about his family history. The Travelers' leader, Markos (RAFFI BARSOUMIAN), arrives in Mystic Falls.

Elena and Stefan start having dreams about an alternate version of their lives; The Travelers move in on Mystic Falls; Matt has a frightening encounter on the Other Side.

Enzo holds Elena, Stefan and Bonnie hostage to uncover the truth about the love of his life. Markos performs a ritual to undo witch's magic.

Damon and Caroline suspect Stefan and Elena of keeping a secret while they hide from the travelers, unaware of the dead man out for revenge. Meanwhile Matt, Jeremy and Bonnie help Tyler get rid of Julian.

When Stefan and Elena escape from Markos' control, only to find themselves Stranded in a remote location, Stefan gets philosophical with Elena about her relationship with Damon. After their attempt to protect the doppelgangers goes badly, Liv and Luke come up with a dangerous new strategy. Damon recruits Matt and Jeremy to help him set a trap for Markos, who turns out to have a devastating surprise of his own. Bonnie finally admits to Caroline that she's been keeping the truth about the Other Side from everyone. Finally, while Bonnie searches desperately for a way to stop Markos, Caroline is witness to an unthinkable act of violence by one of the Travelers.

Damon's plan causes a huge explosion in Mystic Falls, and everyone is caught up in the confusion, leaving a trail of heroism, sacrifice, relief and despair.

Four months have gone by since the Other Side broke down and Bonnie and Damon were lost. Mystic Falls is still a supernatural-free area. Everyone is grieving in their own ways, and some worse than others.

Knowing she needs to come to terms with the loss of Damon, Elena turns to Alaric to help her move on with her life. Enzo convinces Caroline to join him as he tracks down a lead to get Damon and Bonnie back, but Caroline is shocked when they make an unexpected detour and uncover what Stefan has been up to. Meanwhile, Matt worries about Jeremy who is spending time with Sarah, a mysterious girl who has recently arrived in Mystic Falls. Elsewhere, Tripp, leader of the community protection program, makes an interesting confession to Matt about his connection to the town. Lastly, with the Other Side destroyed and gone for good, Damon and Bonnie reluctantly band together to uncover the mystery of where they are and how they are going to get back home.

Caroline admits that she has feelings for Stefan. Bonnie and Damon find clues that make them think they might not be alone.

Damon and Bonnie are trying to come up with a way to come back from the otherside, while Stefan tries to help Elena start fresh.

Elena invites Liam to a party at the corn maze; Stefan shows up asking Caroline for help with a mess created by Enzo; Tyler winds up in a dangerous position.

Elena can't decide whether she wants her memories of Damon back; Alaric asks Elena to look into Jo's background; Tripp puts Damon, Enzo, and Alaric in mortal danger.

Elena is forced to confront her problems; Liv and Tyler get closer; Damon finds a surprising clue that renews his hope.

Elena gets some hopeful news from Alaric and Stefan regarding the Gemini Coven; Tyler tries to help Liv and Luke after learning of disturbing plans the coven has for them; dinner takes a drastic turn for Jo; Kai makes a dangerous discovery.

Elena and Damon enter the prison world to bring Bonnie home. Complications arise when Kai escapes and finds Liv. Stefan finds out the truth about Sarah.

Bonnie tries to replicate her favorite traditions, while reminiscing about happier times with her friends; Sheriff Forbes brings holiday cheer to Caroline at Whitmore College; Alaric turns to Damon and Elena for help when Jo goes missing; Tyler approaches Liv and Luke with a risky plan; Jeremy helps Matt carry out a plan to take down Enzo; Stefan is forced to break some devastating news to Caroline.

As Kai learns how to control his magic, he holds Elena captive; Caroline and Stefan go to North Carolina in search of a cure for Sheriff Forbes; Damon realizes Elena has been kidnapped.

Caroline struggles to save her mother. Damon comes up with a daring new plan. Jo and Kai prepare to merge, but Luke intervenes.

Elena is determined to celebrate Bonnie's birthday; after learning Stefan's secret, Enzo wants to interfere in Sarah Salvatore's life; Caroline struggles to cope with everything going on around her.

Elena and Jeremy reminisce about their past; Caroline and Stefan grow closer; Sheriff Forbes asks Damon for help with a case involving Elena's parents; Enzo lures Matt and Sarah into his plan.

Everybody gathers for the funeral of Liz Forbes. Elena is worried Caroline isn't coping as well as everyone believes.

Stefan blames himself for Caroline turning off her humanity. Bonnie is angry with Damon for aligning himself with Kai. Sarah's life is in danger.

Elena and Damon enter the 1903 prison world to bring back his mother. Stefan intends to exact revenge on Caroline. Bonnie cannot forgive Kai.

Damon concocts a risky plan involving Lily to stop Caroline and Stefan from wreaking havoc; Elena re-evaluates her life as a vampire after learning that Jo is pregnant; Sarah turns the tables on Enzo; Tyler and Matt wind up in danger.

Stefan concocts a plan to get Caroline to turn her humanity back on. Damon wrestles with what he should do with the cure. Enzo seeks answers.

Damon and Elena discuss the ramifications of Damon's offer. Alaric and Jo reluctantly participate in their bachelor and bachelorette parties. Lily continues on a dangerous downward spiral.

Elena and Bonnie help Jo with last minute wedding preparations.

In the aftermath of Jo and Alaric's wedding, an unexpected, and definitely uninvited guest shows up, putting Elena's life in jeopardy. Despite Matt's attempt to leave town to save himself, Bonnie takes matters into her own hands after finding herself on the receiving end of a twisted plan.

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. At the party, Bonnie and Matt uncover a strange mystery involving some unsuspecting residents, while a devastating revelation causes Alaric to reach his breaking point.

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. Meanwhile, desperate to save his brother, Damon follows an unusual lead he has come across, while Matt sends Valerie to Dallas to enlist Alaric's help in the search for Stefan. Finally, when Rayna discovers the emergence of a new threat, she sets off on her own mission to find Stefan before the others do.

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. Meanwhile, in the psych ward, Bonnie meets a young woman named Virginia, who provides her with some valuable information about why The Armory may be after her. Finally, Enzo takes matters into his own hands when he learns some devastating news from Rayna.

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. Elsewhere, when Stefan travels to Dallas and comes face to face with Alaric, tensions escalate and they are forced to confront the fallout from Stefan's absence in Caroline's life. Finally, Enzo learns The Armory's true motives behind their search for Bonnie.

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. Elsewhere, determined to help her best friend, Caroline joins Alaric on a mission and quickly realizes how much she's missed her former supernatural lifestyle. Finally, after their plan takes an unexpected turn, Damon makes a fateful decision that will forever change his relationship with Bonnie.

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. Elsewhere, Enzo tries to hold it together as he painfully watches Bonnie in the fight of her life, while Matt takes matters into his own hands to save one of his closest friends. Alaric also appears.

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 - her and Alaric's twin daughters. Elsewhere, Enzo keeps Bonnie preoccupied by bringing her back to their cabin but when his plan takes an unexpected turn, it'll be up to Damon to make the ultimate sacrifice to save his closest friends. Matt also appears.

Stefan searches tirelessly for Damon and Enzo months after their mysterious disappearance.

No one can accept the loss of Damons humanity that Enzo hopes for too, Damon carelessly tries to prove everyone wrong.

As Enzo continues to fight the control over him, Bonnie finds herself at the center of a deadly game and forced to make a heart wrenching decision involving two of the most important people in her life. At the Armory, Alaric researches a mysterious artifact that he hopes will help in their fight to get Damon and Enzo back. Finally, Damon's downward spiral leads him to Tyler Lockwood who attempts to talk some sense into him before it's too late.

Meanwhile Alaric and Stefan try to find out about the origins of what they are up to, Damon is searching for an artifact so he travels to Texas where he encounters Peter Maxwell who leads him to a new revelation.

Stefan and the others remember what matters most when tragedy strikes close to home.

When her children become the focus of the Siren's latest plan, Caroline (Candice King) takes drastic measures to ensure nothing gets in the way of keeping her family safe. In a race against the clock, Stefan (Paul Wesley) pledges to do everything he can to save the twins, while tensions between Alaric (Matt Davis) and Caroline boil over, leading them to face some harsh realities about the future of their family. Meanwhile, when Enzo (Michael Malarkey) finds himself unable to fight off Sybil's (guest star Nathalie Kelley) latest move, Stefan dives into his subconscious and along the way, sets off a chain of events that leaves him faced with a life-changing decision.

Faced with the fallout from his interaction with Cade (Wolè Parks), Stefan (Paul Wesley) is determined to have one thing go right - Christmas Eve with Caroline. However, when Damon (Ian Somerhalder) and Sybil (Nathalie Kelley) crash their Christmas Eve dinner, which had been joined by Alaric (Matt Davis), Matt (Zach Roerig) and Peter (Joel Gretsch), things quickly take a dark and twisted turn. Meanwhile, in a series of flashbacks to Stefan's past, Cade's attempt to entice him with his mysterious agenda leaves Stefan faced with an unimaginable decision. Kat Graham and Michael Malarkey also star.

Stefan and Damon attend an anger management support group looking for their next victim. Sybil is still alive and teaching a group of high school students who she'll later use as leverage to get Caroline to locate a historical artifact that can be used against her. Meanwhile, Stefan and Damon continue their commitment to Cade as they test the morals of a young doctor, Tara.

Mystic falls is greeted by a traditional celebration and also two reckless brothers. Caroline remains in denial about the future.

Sybil puts Damon in a catatonic state for revenge. Caroline and Bonnie enter Damon's mind and realize Stefan is the key to his fate. Sybil competes with her sister for control of the bell.

Cade returns to Mystic Falls with new assignments for Damon and Stefan that each lead to unthinkable consequences.

Damon makes a deal with Cade to retrieve the Maxwell journal in exchange for Stefan's soul.

Damon and Alaric face an old enemy after finding a weapon that might kill Cade. Stefan is captured by someone from his past. Bonnie tries to reach out to Enzo through Cade.

Damon and Stefan join forces against Cade to protect Elena's casket, while Caroline and Alaric cope with their daughters' growing powers.

A wedding is quickly planned in order for Damon and Stefan to lure a dangerous enemy out into the open.

With the fate of Mystic Falls at stake, Stefan and Damon must fight their greatest enemy for one last battle.

Cade returns to Mystic Falls with new assignments for Damon and Stefan that each lead to unthinkable consequences.

No one can accept the loss of Damons humanity that Enzo hopes for too, Damon carelessly tries to prove everyone wrong.

Knowing she needs to come to terms with the loss of Damon, Elena turns to Alaric to help her move on with her life. Enzo convinces Caroline to join him as he tracks down a lead to get Damon and Bonnie back, but Caroline is shocked when they make an unexpected detour and uncover what Stefan has been up to. Meanwhile, Matt worries about Jeremy who is spending time with Sarah, a mysterious girl who has recently arrived in Mystic Falls. Elsewhere, Tripp, leader of the community protection program, makes an interesting confession to Matt about his connection to the town. Lastly, with the Other Side destroyed and gone for good, Damon and Bonnie reluctantly band together to uncover the mystery of where they are and how they are going to get back home.

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. Elsewhere, when Stefan travels to Dallas and comes face to face with Alaric, tensions escalate and they are forced to confront the fallout from Stefan's absence in Caroline's life. Finally, Enzo learns The Armory's true motives behind their search for Bonnie.

Stefan searches tirelessly for Damon and Enzo months after their mysterious disappearance.

Damon is trapped by Dr. Wes, and realizes scary things about his past.

Enzo holds Elena, Stefan and Bonnie hostage to uncover the truth about the love of his life. Markos performs a ritual to undo witch's magic.

Stefan and the others remember what matters most when tragedy strikes close to home.

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 - her and Alaric's twin daughters. Elsewhere, Enzo keeps Bonnie preoccupied by bringing her back to their cabin but when his plan takes an unexpected turn, it'll be up to Damon to make the ultimate sacrifice to save his closest friends. Matt also appears.

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