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.

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 Damon-less years of his life.

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.

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.

In an attempt to make things right with his brother, Damon offers to have Stefan’s scar magically transferred to him, only to discover that doing so may come with some unexpected consequences. With time running out and Rayna closing in on Stefan, Valerie desperately attempts to reason with Damon before it’s too late.

Elsewhere, after being framed for breaking Rayna out of The Armory, Enzo attempts to clear his name, but not before a violent run-in with Nora forces him to make an upsetting discovery.

While Stefan and Valerie search for a magical herb that can keep him hidden from Rayna, Damon comes up with his own plan to take her down for good. However, while at The Armory, Bonnie makes a shocking discovery about Rayna that brings Damon’s plan to a screeching halt.

Elsewhere, a conversation with Caroline leaves Stefan questioning their future together, while Matt decides it may be time to truly take a stand against the vampires of Mystic Falls. Finally, as the season’s middle chapter draws to a close, Damon’s desire to take himself out of the game ramps up as he races to complete unfinished business with Stefan and Bonnie.

In order to lure a vengeful vampire hunter named Rayna Cruz away from his friends in Mystic Falls, Stefan heads to New Orleans, where Valerie has learned of a safe house that can protect him. Once there, he comes face to face with Klaus Mikaelson, who soon becomes suspicious of his old friend’s unexpected arrival in his city.

Meanwhile, Enzo, who is working on behalf of a mysterious organization called The Armory, approaches Damon and Bonnie with a plan that could protect Stefan from Rayna. Finally, after learning that Alaric has decided to leave for Dallas with the twins immediately, Caroline offers to accompany them on the trip and finds herself contemplating her own future in Mystic Falls.

When complications from her supernatural pregnancy leave Caroline’s life hanging in the balance, Stefan and Valerie take extreme measures to try and save her and the babies. Meanwhile, after uncovering a dark secret about Damon, Enzo uses the information to force Damon into helping him track down Rayna Cruz, a ruthless vampire hunter who is on the loose. However, when Damon’s actions inadvertently put everyone he loves in Rayna’s path, he is forced to make things right before it’s too late.

When his experience in the Phoenix stone leads him to do the unthinkable, Damon finds himself without a care in the world, spiraling out of control and under the influence of a dangerous and reckless Julian. Refusing to give up on his brother, Stefan attempts to reason with Damon only to uncover the devastating reason for his descent.

Elsewhere, Caroline begins having some dangerous side effects as a result of her supernatural pregnancy and is forced to turn to Valerie for help. Meanwhile, Bonnie, Nora and Mary Louise attempt to track down a ruthless vampire hunter named Rayna after they suspect that she has reemerged.

With the traumatic effects of the Phoenix stone taking a toll on his brother, Stefan attempts to help Damon regain his grip on reality, while secretly struggling with his own experience in the stone. Elsewhere, Matt and Bonnie deal with the fallout after Julian and his men take over Mystic Falls, leading Matt to spiral out of control and into trouble with an officer named Penny.

Meanwhile, Tyler returns to town for Alaric’s baby shower and Caroline makes an upsetting discovery involving Alaric and his future plan for the babies.

After finding himself on the wrong end of Julian’s plan to avenge Lily’s death, Damon awakens to find himself trapped inside the Phoenix stone, tormented by a traumatic experience from his time in the Civil War and forced to face his darkest demon in order to get out. On the outside, Bonnie is in a race against the clock to get Damon out before the effects of the Phoenix stone take over and leave him changed forever.

With the holidays in full swing, a search for Julian leads Damon and Stefan to a small town outside of Mystic Falls. While managing a holiday toy drive at Whitmore College, Bonnie seeks help from Nora and the two strike up an unlikely friendship.

Elsewhere, Caroline does her best to navigate her new life as a pregnant vampire, while Alaric grows concerned that the pregnancy is effecting her more than she’s letting on. Finally, after finding himself at odds with Damon, Stefan is forced to take matters into his own hands, setting off a tragic chain of events that leaves their lives changed forever.

As Julian and Lily throw a party to celebrate Mary Louise and Nora’s anniversary, Stefan and Damon set in motion a risky plan to eliminate a new threat posed by Julian. Meanwhile, following a major revelation uncovered by Valerie, Caroline is forced to face her new reality, even as it threatens to destroy her relationship with Stefan. Finally, determined to do what’s best for her family, Lily makes the most difficult decision of her life.

In order to get through to Lily about Julian’s manipulating ways, Stefan and Damon confront their mother with painful memories from their childhood. However, when Lily reveals a dark secret she’s been harboring for over 160 years, Stefan and Damon are left questioning everything they’ve ever known about their family. Determined to prove himself to Lily, Enzo comes face-to-face with Julian and challenges him to a duel, but an unexpected twist threatens to complicate things.

Elsewhere, Matt finds himself in the middle of a deepening mystery involving the residents of Mystic Falls, and Caroline’s world is turned upside down when Valerie reveals some life-changing news to her.

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.

After realizing the downward spiral he was on, Damon decides he’s going to turn over a new leaf and that his actions moving forward will do right by Elena. Lily prepares for the arrival of a special figure from her past, while Enzo stands by not sure what to expect.

Elsewhere, at Caroline’s urging, Stefan comes face-to-face with Valerie and learns some upsetting details about her past, while Enzo and Bonnie find themselves at odds when they’re forced to fend off a violent threat. Finally, when Bonnie learns some disturbing information involving the Phoenix stone, she is forced to confront Alaric.

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. Elsewhere, when the fallout of Damon’s actions gains the unwanted attention of Mary Louise and Nora, Stefan and Caroline are forced to spend the night distracting the girls at Whitmore College’s Heaven & Hell ball. Finally, after suspecting that she’s up to something, Enzo sets off on a mission to find out what Valerie is hiding, while a plan set by Alaric and Bonnie leaves their worlds turned upside down.

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.

When an impulsive decision by Damon threatens to unravel a carefully negotiated deal between Stefan and Lily, he has no choice but to make amends with his mother before things spiral further out of control. However, Lily remains one step ahead and carries out a harsh plan that hits Damon where it hurts most.

Elsewhere, after returning to Whitmore Collage, Alaric turns to Bonnie for help with a mysterious and potentially dangerous artifact he has obtained, while Matt is forced into making a risky life or death decision. Meanwhile, Caroline, who finds herself a pawn in Lily and the heretics’ plan for retribution, uncovers a shocking detail about Stefan’s past.

After a twisted plan left the life of his girlfriend Elena linked to that of his best friend Bonnie, Damon is forced to navigate his new reality without the love of his life. A newly empowered Bonnie has decided that she will be Damon’s moral compass and keeps a close eye on him as he, in turn, cautiously keeps tabs on Alaric, following the loss of his fiancée Jo. Meanwhile, as he waits for Caroline to sort out her emotions, Stefan takes an active role in protecting the town from Lily and her family of Heretics, who have wasted no time wreaking havoc in Mystic Falls.

Elsewhere, Enzo struggles to find his place in Lily’s new life, and is quickly forced to decide where his true loyalties lie. Finally, with the stakes higher than ever, Matt, who has recently completed his deputy training program, teams up with Stefan and Caroline to put a stop to the Heretics, but an unexpected turn of events leaves one of them in a dangerous position.

In the aftermath of Alaric and Jo’s powerful nuptials, things take a dramatic turn when an uninvited guest shows up, leaving Elena in terrible jeopardy. Despite Matt’s advice to leave town to protect herself, a defiant Bonnie takes matters into her own hands after finding herself on the receiving end of a twisted plan. As Stefan and Caroline reach an emotional crossroad in their relationship, a reunion with Liv leaves Tyler faced with a decision that could change his life forever. Meanwhile, Lily’s reckless actions cause Stefan to realize the lengths to which his mother will go to reunite with her “family.” Finally, after a devastating chain of events, Damon is forced to make the most difficult decision of his life.

It’s Alaric and Jo’s wedding day and Elena and Bonnie do their best to help a stressed out Jo with the last minute preparations. After uncovering some life-changing news that Damon has been keeping from him, Stefan takes his brother on a road trip to give him some perspective on his future with Elena. Elsewhere, when Caroline returns to Mystic Falls after dealing with the fallout of her humanity-free rampage, she begins making amends with her friends and comes to a realization about her and Stefan’s prospects of being together. Finally, when Bonnie begins having vivid nightmares that Lily is coming after her, she enlists Matt’s help in taking Lily down.

As Alaric and Jo reluctantly participate in their bachelor and bachelorette parties, Damon and Elena discuss the ramifications from an impulsive offer that Damon makes. Unsure of what to do, Elena turns to Bonnie and Jo for advice, but is left conflicted when Bonnie raises some unanticipated concerns. When Enzo realizes Lily is on a dangerous downward spiral, he asks Stefan to help intervene before it’s too late. Lastly, fed up with the supernatural threats that plague their town, Matt takes his frustrations out on Tyler, while Alaric considers a life-changing piece of advice.

Wrestling with whether or not to tell Elena about the cure, Damon brings up their future together and what life would be like if they weren’t vampires. Meanwhile, it’s all hands on deck when attempts to stop a humanity-free Caroline doesn’t go as planned. Elsewhere, when Bonnie discovers that Damon has betrayed her trust, she takes matters into her own hands, setting off a chain of events that leaves Damon dealing with the fallout. Lastly, after being forced to face his traumatic past, Enzo sets out for answers and is surprised when he learns the truth about the day he was turned into a vampire.

With their humanity turned off, Stefan and Caroline begin wreaking havoc at Whitmore, leaving Damon to come up with a risky plan involving Lily. After rushing to help Jo treat victims of Stefan and Caroline’s latest killing spree, Elena discovers Jo is pregnant, prompting her to reevaluate her own life as a vampire. Meanwhile, when Sarah boldly turns the tables on an unsuspecting Enzo, he is forced to open up about his tragic past. Lastly, at Scull Bar, a twisted round of karaoke leaves Tyler and Matt in a dangerous situation.

With the help of Bonnie and Kai, Damon and Elena set forth a plan to rescue Damon’s mother Lily, who is trapped in the 1903 prison world. Meanwhile, when Caroline’s plan for Stefan backfires, she is left to pick up the pieces. Elsewhere, back at Whitmore College, Enzo and Alaric’s attempt to reel Caroline back in doesn’t quite go as planned when they realize they’re outmaneuvered. Lastly, an unexpected gift from Bonnie leaves Damon shaken to his core.

After shutting off her humanity following the death of her mother, Caroline gives her friends an unexpected ultimatum. Not knowing how to handle the new Caroline, Stefan’s attempt to intervene sets off a dangerous chain of events, leaving him and Elena in a race against the clock. Meanwhile, after seeking answers from Kai about the prison world, Damon’s world is turned upside when he learns some devastating news about his mother Lily. Elsewhere, Enzo finds himself becoming increasingly intrigued by Sarah Salvatore, and Bonnie begins to struggle with the effects of being back in the real world.

After assigning tasks to each of her friends, Caroline attempts to deal with her current situation as reality begins to set in around her. While spending the day with Caroline, Elena grows concerned when she starts noticing a strange change in her behavior. Meanwhile, Alaric becomes wary when Kai, who has begun experiencing unexpected consequences from the merge, turns to Jo, desperate for her help. Elsewhere, while Bonnie finds herself in an unfamiliar situation, Matt and Tyler contemplate a major life change. And when Damon offers Caroline advice on how to cope with everything going on around her, it forces him to revisit painful memories involving his own mother.

It’s Jeremy’s last day in Mystic Falls and Elena puts on a brave face as they reminisce about their past. Stefan and Caroline find themselves growing closer as they prepare Caroline’s family cabin for her mother to live out her final days. While packing up her office, Sheriff Forbes turns to Damon for help solving one of her remaining open cases involving Elena’s parents. Elsewhere, when a violent confrontation with Enzo leaves Jeremy wondering whether he should leave or not, Matt finds his own life on the line after Enzo lures him and Sarah Salvatore into his dangerous plan. Lastly, Caroline rushes to the hospital after learning her mother has taken a turn for the worse.

Determined to celebrate Bonnie’s birthday, Elena convinces Jeremy that it’s what Bonnie would have wanted. After piecing the broken ascendant back together, Elena, Jeremy and Damon attempt to send Bonnie a message, but the situation turns dire when they make an unsettling discovery. Meanwhile, after uncovering Stefan’s secret about his great-niece Sarah Salvatore, Enzo enlists a reluctant Matt to help interfere with her life. Elsewhere, Stefan keeps a close eye on Caroline as she unconventionally attempts to cope with everything going on around her. Lastly, realizing it might be time to move on with his life, Jeremy contemplates leaving Mystic Falls for good.

When Liv and Luke’s father arrives to town to celebrate their birthday, they try and convince him to let Jo and Kai take their place in the merge ceremony. After Tyler finds out that the merge is happening sooner than he expected, he urges Liv to let him talk to her father. Meanwhile, after Caroline’s plan to cure her mother takes an unexpected and devastating turn, Elena, Stefan and Damon gather at the hospital, while Jo attempts to save Sheriff Forbes’ life. Lastly, with the merge set to take place, Damon’s risky plan quickly sends things spiraling out of control, forcing one of the twins to take matters into their own hands.

More powerful than ever, Kai holds Elena captive while he learns to control his newly acquired magic. At the Salvatore mansion, Liv and Alaric try to prepare Jo for the impending merge ceremony with Kai, but they quickly realize Jo is weaker than they thought. After bringing Sheriff Forbes home from the hospital, Caroline travels with Stefan to North Carolina in search of a cure for her mother’s cancer. Meanwhile, Stefan, who has his own intentions for traveling to North Carolina, is caught off guard when Enzo shows up demanding to know what Stefan is hiding. Lastly, when Damon discovers Elena has been kidnapped by Kai, he is forced to rethink his strategy after an unexpected visitor throws a wrench into his plan.

With the holidays approaching, Bonnie attempts to replicate her favorite traditions, while reminiscing about happier times with her friends. Not able to return home to Mystic Falls for her favorite time of the year, Caroline is surprised when Sheriff Forbes brings the holidays to her at Whitmore College. Meanwhile, after discovering that Jo has gone missing, Alaric turns to Damon and Elena for help, while Liv and Luke find themselves at odds when Tyler approaches them with a risky plan. Elsewhere, Jeremy helps Matt carry out a plan to take down Enzo but grows concerned when Matt takes things too far. Lastly, Stefan is forced to break some devastating news to Caroline.

Damon finds himself in hot water after he carries out a plan that requires Alaric’s unwilling participation. When Elena shares some hopeful news with Jeremy about Bonnie, she is caught off guard by his reaction. Liv helps Damon and Elena with their plan to get Bonnie back, but when things take an unexpected turn, she’s left with a difficult choice to make. Elsewhere, Matt takes matters into his own hands when Enzo’s actions cross the line, and Kai’s existence continues to be a dangerous threat.

As Caroline and Elena prepare to host Friendsgiving at the dorm, they receive some hopeful news from Alaric and Stefan, who have traveled to Portland to gather some information regarding the Gemini Coven. Tyler is determined to help Liv after she and Luke reveal some disturbing information about their witch lineage and the impending plans their coven has for them. Meanwhile, dinner takes a drastic turn when Jo, who has revealed some painful details about her past, finds herself fighting for her life, leaving Alaric scrambling to help from a distance. Finally, Kai makes a dangerous discovery that brings him one step closer to his release.

When the past comes back to haunt her, Elena is forced to face her problems head on. After a night out at the annual Whitmore Medical Center Fundraiser, Jo opens up to Alaric about her own tragic past. Meanwhile, Stefan, Matt and Enzo resort to extreme measures when Tripp withholds information about his vampire-killing operation, and Caroline is in a race against the clock when Sheriff Forbes gets caught in the middle of a dangerous plan. Elsewhere, Tyler and Liv grow closer, and Damon stumbles upon a startling clue that renews his hope.

When Alaric realizes that Jo can’t be compelled, he asks Elena to do some digging into her background. After learning that Enzo has been captured by Tripp, Caroline teams up with Matt and Stefan to rescue him before Tripp learns their true identities. Armed with some new information about her past, Sarah breaks into Tripp’s office and is surprised when she finds Matt there, doing some investigating of his own. Meanwhile, Elena is forced to deal with the consequences of her actions, and Jeremy hits rock bottom, lashing out in a destructive way. Lastly, Damon is determined to take matters into his own hands when he receives some upsetting news.

With Homecoming around the corner, Elena invites Liam to attend a party at the corn maze with her. Instead of attending the homecoming festivities, Caroline is preoccupied after Stefan shows up unexpectedly and needs her help cleaning up a mess created by Enzo. Heeding Elena’s advice to be more social, Alaric reluctantly attends the party, but a devastating accident quickly leaves him and Jo rushing to save lives. Elsewhere, Tyler finds himself in a dangerous position when his werewolf curse is put to the test, and an emotionally embattled Stefan comes clean to Caroline about his intent to move on from Mystic Falls. Lastly, Damon and Bonnie make an important discovery that affects their quest to get back home.

When Damon and Bonnie realize that uncovering a time in Damon’s past may provide clues to finding their way home, Damon is forced to relive one of the worst days of his life. After an awkward run-in with Jo at the hospital, Alaric steps in to help Jeremy get his life together and cope with the loss of Bonnie. Elsewhere, Stefan attempts to show Elena what it’s like to start over and create a new identity, while an unsuspecting Matt finds himself in a disturbing situation when Tripp lets him in on a dark secret. Lastly, Stefan, who is desperate to regain some normalcy in his life, is stunned when an unexpected visitor shows up.

In an attempt to bring some fun back into their lives, Elena persuades Caroline to meet her at the swimming hole where she plans to introduce her to Liam. Tyler, still working on controlling his anger issues, asks Liv for a favor and is surprised when she makes an unexpected confession. Stefan arrives back in Mystic Falls looking for Enzo and is caught off guard when he notices a strange change in Elena. Meanwhile, at the lake, Enzo’s actions cause Matt to make a startling revelation, and Jeremy makes a discovery about the anti-magic spell that could potentially put Elena’s life in danger. Elsewhere, Damon and Bonnie stumble upon clues that lead them to believe they’re not alone.

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.