Reeling from the death of her parents, 17-year-old Elena becomes interested in a handsome new student named Stefan, who's hiding a dark secret.
Elena goes to the Salvatore house to talk to Stefan, but finds Damon there instead, who reveals surprising information about Stefan's past. Vicki begins to remember the attack.
Elena invites Stefan and Bonnie to dinner, hoping that the two will bond, but the evening is disrupted by the unexpected and unwelcome arrival of Damon and Caroline.
Stefan escorts Elena to the town's Founder's Party. At the party, Damon tells Elena a story about the Salvatore family, leaving Elena with questions Stefan refuses to answer.
Stefan is hopeful of his plan to get rid of Damon, and decides to reveal parts of his past to Elena. Bonnie seeks advice from her grandmother.
In flashbacks, Stefan reveals to Elena the Salvatore family history, including how his rivalry with Damon began. In the present, Damon impulsively takes control of Vicki's future.
Bonnie's abilities surprise Damon. Elena asks Jeremy not to see Vicki. Matt takes Vicki to the high school Halloween dance, but the night takes a terrifying turn.
Stefen gets a surprise visit from old friend Lexi. Caroline tries to get Damon's Medallion back from Bonnie.
Jeremy gets a break from the mysterious new history teacher, Alaric Saltzman. Damon reveals to Stefan the stunning reason he returned to Mystic Falls.
When Sheriff Forbes tells Damon of another attack, he offers to track down the killer, learning startling information about the town's founding families.
Damon goes to Georgia to suprise an old flame, Bree, and enlist her help. Meanwhile, Stefan uncovers a startling clue to the past.
The Mystic Grill's Ben comes to Bonnie's aid. Damon and Stefan accompany Elena to a school dance with a 1950s theme. Alaric introduces himself to Damon.
Stefan and Damon recall the incidents that led to the rift in their relationship.
Jeremy asks Anna to a party in the woods. Stefan, Damon and Elena work with Bonnie and Grams to open the tomb, and are shocked by what they discover.
Recurring guest star Melinda Clarke appears as Kelly, Matt's long-lost mother. Sheriff Forbes asks Damon to be part of a fundraising bachelor auction.
Anna brings a surprising guest to pay a visit to Damon. Elena and Stefan go on an awkward date with Caroline and Matt. Melinda Clarke appears as Kelly.
Stefan is forced to make a frightening decision. Matt is hopeful that his mom, Kelly, will stay. And, after Caroline's car breaks down in a storm, she makes a horrific discovery that shocks everyone in town.
Stefan displays a rare party attitude and Damon's attempt to find out why Elena's uncle, John Gilbert has returned to town takes an ugly turn.
Elena and Caroline compete in a beauty pageant. Spencer Locke appears as one of the contestants. John Gilbert tries to scare Damon.
Elena learns what happened when Damon and Stefan were turned. Pearl has an ugly confrontation with John Gilbert. Jeremy and Anna get closer.
Isobel returns to town and stuns Alaric with her attitude and her demands that he arrange a meeting with Elena.
Damon and Alaric try to stop John Gilbert from setting a plan in motion to bring Founder's Day to an end amid chaos, destruction and death.
Elena comes home to a nightmare; Damon realizes Katherine has returned; Tyler receives a surprise visit from his uncle.
When a confused and desperate Caroline leaves the hospital and joins her friends at the Mystic Falls Carnival, Damon wants to take immediate action.
Elena, Damon and Alaric go to Duke University to find Isobel's research into the paranormal and look for clues to the mystery surrounding the Lockwood family; Stefan faces a new danger in the woods; Tyler makes a shocking discovery about Mason.
Katherine recalls the past.
Tyler learns more about the Lockwood family curse from Mason, and Sheriff Forbes receives startling information.
Katherine chooses a new victim. Bonnie discovers new information about Mason and shares it with Stefan.
Stefan and Damon decide on a new plan to deal with Katherine at the masquerade ball.
Stefan and Damon come to Elena's assistance and, in the process, learn surprising new information.
Elena puts herself in a dangerous position as she searches for the truth about Katherine's past and what her own future may hold. Knowing that Stefan would never agree to her plan, Elena swears Caroline to secrecy. Damon uses a new-found confidant to help him try to discover the real purpose and power of the moonstone. Jeremy and Bonnie meet Luka, a new student with a surprising family history.
Elena decides to take matters into her own hands and offers a tempting incentive to Rose for her help. When things take an unexpected turn, however, Rose calls on Damon to deal with the plan Elena has set in motion. Jeremy's reckless attempt to help Bonnie retrieve the moonstone lands him in a life-threatening position and forces Stefan to put himself in danger. Bonnie and Luka form a closer connection. Tyler shows Caroline the Lockwood cellar, where she makes a discovery that leaves them both terrified.
As the full moon nears, Caroline helps Tyler prepare for his transformation. Meanwhile, Damon and Alaric are suspicious when a stranger shows up looking for Mason.
While Damon tries to get the truth out of Jules, he asks Elena to keep an eye on Rose, a situation that turns unexpectedly dangerous.
Johnathan Gilbert's return to Mystic Falls is an unhappy surprise to Elena, Jenna and Damon. Stefan does his best to reach out to a confused Tyler.
Stefan and Elena attempt a romantic weekend getaway, not realizing that they've been followed. Damon attends a tea at the Historical Society.
Stefan tells Elena about his darkest days. Trying to catch Elijah off guard, Damon arranges a dinner party.
Katherine's mind games cause everyone frustration, but Elena, Stefan and Damon realise that her knowledge of Mystic Falls' history could be crucial to their survival.
Isobel unexpectedly returns, leaving Jenna devastated. Bonnie attempts to harness her ancestors' power. Stefan and Damon realise that they have a new weapon.
As the students get ready for a 1960s-themed dance at the school, Elena begins receiving disturbing messages from the ancient vampire Klaus from an unusual source.
Stefan and Damon are angry when they find out that Elena has taken matters into her own hands in the battle against Klaus. Tensions also rise between the brothers over the best way to protect her.
Damon reveals that he is willing to go to incredible lengths to protect Elena from falling victim to Klaus's plans. Stefan and Elena spend a romantic day together.
Despite an unanticipated act of courage, events spin out of control in a frightening way.
Lives hang in the balance as the consequences of the sacrifice ritual play out.
It's Elena's 18th birthday, and as she searches for Stefan, Damon tries to keep her from doing anything that might draw Klaus's attention.
Damon and Alaric reluctantly go along with Elena's new strategy to find Stefan, leading Damon into a dangerous fight with an unexpected enemy.
Klaus and Stefan arrive in Chicago, where Stefan is reunited with a vampire who hasn't really moved on from her interest in him decades earlier. In a flashback to Chicago in the 1920s, Stefan comes face-to-face with a shocking chapter from his wild past. After Damon gets a tip on Stefan and Klaus' whereabouts from an unexpected source, he and Elena follow their trail. Back in Mystic Falls, Tyler is concerned about Caroline and turns to Sheriff Forbes for help.
Still in Chicago, Klaus enlists the help of a witch called Gloria to try to discover why his plan is not working. Gloria's spells reveal some intriguing glimpses of the truth but she soon realises she need Stefan to complete the puzzle. Back in Mystic Falls, a new enemy pushes Damon over the brink with devastating consequences, while Caroline struggles with her own emotional issues.
Despite all that has happened, Caroline is determined to see that Elena, Bonnie, Matt and Tyler all enjoy a traditional Senior Prank Night before the school year begins at Mystic Falls High School. However, when uninvited guests show up, it doesn't take long for the evening to take a deadly turn. Damon convinces Jeremy that he can use his new connection to the other side to help find a way to defeat Klaus. Finally, Klaus deepens his hold on Stefan and uses him for increasingly violent and dangerous purposes.
On the first day of their senior year, Elena, Caroline, Bonnie and Matt are still reeling from recent events, while Tyler seems to be enjoying everything a little too much. Damon is annoyed by a new houseguest, and everyone is surprised by the arrival of a new student in Alaric's history class. Matt asks Bonnie for help when he realizes he made a serious mistake. Meanwhile, Stefan continues to carry out his latest assignment from Klaus.
As Mystic Falls prepares to celebrate the traditional Illumination Night, the town is invaded by spirits of the dead. After a particularly violent encounter with an angry spirit, Damon asks Bonnie to find the reason behind the ghosts' surprising power. Elena convinces Jeremy to use his connection to the other side to help her find a new way to reach Stefan, leading Jeremy to a terrible choice. Finally, Alaric discovers a long-hidden clue to the past.
With help from Elena and Bonnie, Alaric tries to decipher the meaning behind his recent discovery Elena and Rebekah engage in a mean-girl power struggle, until Rebekah finally reveals some of her family's ancient secrets and the violent past she shares with Klaus and Elijah. Damon tries a reckless new approach to make a breakthrough with Stefan, and they're both surprised by an unlikely ally.
On the night of the Homecoming dance, Rebekah opens up to Elena about why the evening is so important to her, leaving Elena with conflicting emotions. Caroline and Matt are both shocked at Tyler’s behavior throughout the evening. The night takes a surreal turn when Klaus puts his latest plan into action. Determined to outsmart Klaus, Damon enters into a dangerous partnership, leading to a terrifying turn of events.
Stefan has hidden the coffins containing the bodies of Klaus’ family, and Klaus quickly turns to violence to convince Damon and Elena that no one will be safe until he finds Stefan and gets his family back. Tyler continues to make the most of his new abilities as a hybrid, but he has to face the disturbing consequences of his actions as well. After a terrifying incident, Elena and Alaric grow increasingly concerned about Jeremy’s attitude and, ultimately, his safety. Alaric meets the beautiful Dr. Fell, who is intrigued with his amazing ability to heal. While trying to strike a deal with Klaus, Elena delivers news that truly shocks him.
Although Caroline is in no mood to celebrate her 18th birthday, Elena, Bonnie and Matt surprise her with a small party in an unusual location. Damon and Stefan disagree on the best way to handle Klaus , and a reckless Stefan decides to test his theory by taking things to dangerous extremes. Bonnie is concerned when Elena tells her about Jeremy's new plans. At a Founder's meeting, Alaric once again runs into Dr. Fell, who is in the middle of an argument with her ex-boyfriend, the medical examiner. Tyler refuses to go along with Klaus' latest demand, and is surprised when Klaus seems to accept his decision.
Prophetic dreams about the mysterious fourth coffin lead Bonnie and Elena to a surprising source, while Tyler seeks help to break free from Klaus' bond so he can be with Caroline. Alaric's new friend Dr. Fell has a secret no one sees coming, and Stefan's interference in Elena's life reveals something that surprises even him.
Sheriff Forbes delivers some disturbing news to Alaric and Elena about the weapon used in a recent murder. In the Salvatore brothers’ escalating quest to kill Klaus, Stefan turns to Bonnie and Abby, while Damon reaches out to an old acquaintance for help in setting up an elaborate plan. Intent on a plan of his own, Klaus hosts a strange dinner party, where he reveals another story from his family’s violent past until an unexpected guest brings the party to an end. Meanwhile, Caroline is heartbroken when she is unable to stop a tragedy from unfolding.
Elena is surprised to receive an invitation to a formal ball, and when Damon and Stefan hear the party is being hosted at Klaus’s newly renovated mansion, they both insist on attending the event with her. Caroline and Matt also receive invitations to the ball from unexpected admirers. At the elegant party, Elena learns of a horrifying plan that could lead to numerous deaths and she must decide who she can trust with her new information. Caroline discovers a side of Klaus no one would have suspected. Finally, after an evening of violence and dashed hopes, Damon finds a new way to cope.
After starting her day with a startling discovery of Damon’s latest indiscretion, Elena is frustrated to find that none of her friends agree with her on how they should react to the Original family’s internal power struggle. Once again caught up in the destiny of the Bennett witches, Bonnie and Abby find themselves playing a part in a ritual to appease the spirits of nature. When Elijah gives Damon and Stefan a dangerous ultimatum that puts Elena in danger, they turn to Alaric and Meredith for help with a plan that leads them to a terrible choice.
The present-day murders in Mystic Falls remind Damon of a similar crime spree a century earlier. Flashing back to 1912, Damon recalls a beautiful vampire.
A century after their first encounter, Damon and Sage meet again at the ceremony to kick-off the restoration of Wickery Bridge. Damon is surprised to learn the reason Sage has returned, and pleased when she devises an unusual method to help him figure out what Rebekah is up to. Abby is having a hard time adjusting to her new reality, despite Bonnie and Caroline’s efforts to help. When Damon informs Elena of Stefan’s latest struggles, she reaches out to Stefan to help her save a friend in danger, in hopes that it will help bring Stefan even closer to his humanity. Finally, when Damon discovers a new secret weapon, he lets Stefan in on the news.
Stefan's emotional turmoil leads him to a dangerous confrontation with Klaus and, later to a heartbreaking moment with Elena.
Caroline is thrilled when Tyler returns to town, but Tyler soon suspects that something has been going on between Caroline and Klaus. Matt tries to keep Rebekah busy.
The 1920s Decade Dance takes a deadly turn when Damon and Stefan realize they need the help of Matt, Jeremy and Bonnie to undo a spell that could be devastating for everyone.
Klaus acts on his intentions to leave town with Elena, but finds resistance from a surprising new enemy. Damon and Stefan have a surprisingly candid conversation about the future.
Determined to protect his sister, Jeremy makes a decision that will change everything; Bonnie makes a secret deal that has heartbreaking consequences.
In the fourth season premiere, Elena awakens after the accident to find the thing she dreaded most has come true. Damon is furious with Stefan, and takes out his rage on Matt.
Stefan and Damon argue about what is best for Elena. Jeremy and Matt are surprised to see a girl they used to know, April, enrolling at Mystic Falls High.
Elena learns confronting Rebekah can be dangerous. Tyler gets a surprise visit from Hayley, a werewolf who helped him with Klaus.
At a fraternity costume party, Damon gives Elena a lesson in choosing a victim. Klaus reveals an encounter with a group of vampire hunters - flashing back to 12th century Italy.
Stefan and Klaus form an uneasy alliance to try and contain the danger that Connor has unleashed. Professor Shane works with Bonnie.
Terrifying hallucinations leave Elena shaken and confused and she makes a painful confession to Stefan. Matt gives Damon startling information about Professor Shane.
At the annual Miss Mystic Falls Pageant, Elena and Caroline give April advice, while Tyler and Hayley work together on a secret project.
Damon and Stefan visit New Orleans in hopes of finding someone who remembers their last visit in 1942.
It's a winter wonderland in Mystic Falls. Plus, Professor Shane reveals a piece of ancient history that leaves everyone speechless.
Rebekah is back with a vengeance. Bonnie is uncomfortable when her father, Rudy Hopkins, accepts the role of Interim Mayor.
Jeremy is furious when Klaus tries to control him by putting Matt’s life in danger. Damon coaches Jeremy as he prepares to take on Klaus’ new vampires, but they find that Kol has beaten them to it. Kol makes it clear that he will stop at nothing to convince everyone to give up the search for the cure. Looking for a new ally, Rebekah reminds Stefan that they were once close friends. When Sheriff Forbes and Mayor Hopkins question Shane about his involvement in the Founders’ Council deaths, Bonnie steps in with questions of her own. Elena tries to negotiate with Klaus to keep Jeremy safe.
When the 1980s Decade Dance at the high school is cancelled by Mayor Hopkins, Stefan finds a charming way to make it up to a disappointed Rebekah.
Shane leads an expedition to a desolate island, where he believes the secret of the cure lies hidden. Rebekah and Elena continue their bitter rivalry.
Damon has an ugly run-in with a Hunter, Vaughn, and realizes he is one of the Five. Stefan admits his feelings about possibly becoming human.
Damon and Rebekah learn an unexpected bit of recent history from Vaughn. Bonnie reveals the rest of Shane's plan.
Elena's new outlook has everyone concerned. Damon and Rebekah work together, but his unwanted advice catches her off-guard. Klaus tries to use Hayley.
Realizing that Elena needs some time away from Mystic Falls, Damon takes her to New York City. Flashbacks reveal Damon's hedonistic life there in the 1970s.
While in a small town in Pennsylvania with Rebekah, Elena has a surprising encounter with Elijah. Klaus receives Caroline's reluctant help.
When Caroline's plans for the perfect Senior Prom night are disrupted by Elena, she turns to an amused Klaus for a solution. Bonnie makes a terrifying discovery.
Klaus returns to his past in New Orleans and meets with his former protégé, Marcel, a charismatic vampire with control over the city's inhabitants.
The Salvatore brothers ask for backup from a surprising source when Elena calls their bluff. Katherine is suspicious when Bonnie makes her an offer.
Someone has been attacking patients at the hospital. A violent wind storm causes a power outage and ghosts suddenly appear - some with good intentions and some bent on revenge.
It's Graduation Day. Damon's life is in danger and Elena faces an epic confrontation. Plus, Stefan discovers a horrifying clue to the mystery surrounding Silas.
As the fifth season opens, Elena, after a passionate summer with Damon, heads to college nearby with Caroline as her roommate. Plus, a terrifying appearance by Silas.
A fellow Whitmore student named Jesse gives Elena some intriguing information about Professor Wes Maxfield. Damon asks for help finding Stefan.
Elena and Katherine both dream that Stefan is in danger and convince Damon to help them find him. But their plans are thwarted by a mysterious woman who seems to know everything about Stefan's past and Damon's disturbing future.
Damon and Elena try to help Stefan through a confusing time, which ends up taking Elena on an emotional journey. Caroline makes an effort to know Jesse better.
Elena meets a sad and secretive student on campus. Elena and Damon attend the Whitmore Historical Ball dressed as Anne Boleyn and Henry VIII. While there, Elena receives a disturbing message from Dr. Maxfield. Nadia reveals her surprising history to Katherine;. Silas demands that Damon commit an unthinkable act.
Damon and Elena are skeptical of Silas's new goal; Tessa realizes she was outsmarted by Silas; after discovering a new consequence of becoming human, Katherine decides she needs a new place to stay; Bonnie is impressed with Jeremy.
Dr. Wes gives Katherine some disturbing news. Jeremy and Bonnie share a glimmer of hope after talking with Amara. Silas fails to keep a promise which causes Damon to turn to Tessa for help with his new plan. Stefan makes a heartbreaking confession to Damon and Elena.
Elena and Caroline plan a big party at school, but their plans are interrupted when Jesse suddenly needs Caroline's help. Meanwhile, Damon makes a terrifying discovery about a secret society.
Caroline offers Stefan an unusual form of therapy. Meanwhile, Damon tells Elena about a terrible ordeal in his past that he has kept secret for decades, and she shares with him some disturbing information she recently learned about her family.
Damon is forced to deal with a part of his past he thought was gone forever when Dr. Wes unleashes a secret weapon to stop him from rescuing Elena. Elena learns about the dark history of Whitmore College. Katherine turns to Matt for help.
Katherine recalls the traumatic night in 1490 when she gave birth to a daughter who was immediately taken from her. Meanwhile, Nadia creates a frightening plan to protect her mother; and Caroline indulges in some scandalous behavior.
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.
Caroline convinces Elena and Bonnie to attend Whitmore College's Bitter Ball for broken-hearted students. Bonnie meets a fellow student who appears to be dabbling in witchcraft. Tyler worries about Matt's relationship with Nadia. Damon and Enzo resort to violence to convince Bonnie and Jeremy to help them get revenge, but their plan takes a horrifying turn.
Damon's behavior escalates from destructive to deadly. Stefan begins to regret their last conversation and tries to track Damon down and intervene. Dr. Wes enlists the Travelers to set a trap that will test Damon's friendship with Enzo; and a talk between Caroline and Stefan leads to a horrifying realization.
Nadia recalls her centuries-long search for her mother. Stefan, Caroline and Matt come up with a desperate plan to save Elena's life. Damon baits Tyler into an ugly confrontation and seeks revenge against Dr. Wes. Bonnie learns a terrifying secret that threatens the lives of all her friends.
Damon tries to find the right way to make a disturbing confession to Elena. Caroline discovers a scary secret in Dr. Wes' files. Enzo claims to have a solution everyone is searching for. Sloan reveals new information on the importance of doppelgangers.
Bonnie has an unsettling encounter with Luke, and learns more about his family history. The Travelers' leader, Markos, arrives in Mystic Falls.
Stefan and Elena experience unsettling dreams of the life they might have had together. Bonnie has a disturbing encounter with Grams. Enzo searches for a woman he loved decades ago. Bonnie learns that Jeremy is working with Liv. Matt has a terrifying encounter with inhabitants of 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.
Stefan and Elena become stranded in a remote location, after escaping from Markos, and he gets philosophical about her relationship with Damon. Damon sets a trap for Markos. Bonnie admits that she's been keeping the truth about the Other Side from everyone. Caroline witnesses 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.
Elena comes to terms with the loss of Damon with the help of Alaric. Enzo convinces Caroline to join him as he tracks down Damon and Bonnie. 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, tells 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. 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 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.
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.
The transfer of Rayna's life also turns Bonnie into a huntress, who must turn on all her supernatural friends, but fights that, hating only Damon, by inducing herself in a deep sleep, merely slashing in nightmares. So the vampires try to intrude her dreams and find a way out. Caroline sends Alaric home and goes first, but not only fails, she actually gets marked up as fatal target. Nevertheless, Enzo and the brothers take the same risk, to little avail. Sheriff Matt has his own mission.
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.
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.
Tasked with finding a mysterious artifact, Damon’s latest mission takes him to Texas where a violent run-in with Peter Maxwell leads to a surprising revelation. Meanwhile, after gaining the upper hand in their fight to save Damon and Enzo, Stefan and Alaric team up and uncover the origins of the mysterious force they’re up against. Finally, Matt returns to the fray after his past and present collide in an unexpected way.
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 takes drastic measures to ensure nothing gets in the way of keeping her family safe. In a race against the clock, Stefan pledges to do everything he can to save the twins, while tensions between Alaric and Caroline boil over, leading them to face some harsh realities about the future of their family. Meanwhile, when Enzo finds himself unable to fight off Sybil’s 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, Stefan is determined to have one thing go right – Christmas Eve with Caroline. However, when Damon and Sybil crash their Christmas Eve dinner, which had been joined by Alaric, Matt and Peter, 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.
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.
