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- 2009–201742mTV-148.9 (1.5K)TV EpisodeDirectorCarol BankerStarsPaul WesleyIan SomerhalderKat GrahamCade returns to Mystic Falls with new assignments for Damon and Stefan that each lead to unthinkable consequences.
- DirectorJulie PlecStarsPaul WesleyIan SomerhalderKat GrahamWith the fate of Mystic Falls at stake, Stefan and Damon must fight their greatest enemy for one last battle.
- 2009–201742mTV-148.0 (976)TV EpisodeDirectorTony SolomonsStarsPaul WesleyIan SomerhalderKat GrahamDamon 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.
- 2009–201741mTV-148.8 (1.3K)TV EpisodeDirectorPascal VerschoorisStarsPaul WesleyIan SomerhalderKat GrahamDamon and Stefan join forces against Cade to protect Elena's casket, while Caroline and Alaric cope with their daughters' growing powers.
- DirectorDarren GenetStarsPaul WesleyIan SomerhalderKat GrahamDamon makes a deal with Cade to retrieve the Maxwell journal in exchange for Stefan's soul.
- 2009–201742mTV-147.9 (946)TV EpisodeDirectorGeoffrey Wing ShotzStarsPaul WesleyIan SomerhalderKat GrahamMystic falls is greeted by a traditional celebration and also two reckless brothers. Caroline remains in denial about the future.
- DirectorKellie CyrusStarsPaul WesleyIan SomerhalderKat GrahamSybil 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.
- DirectorJames L. Thompson IIIStarsPaul WesleyIan SomerhalderKat GrahamStefan and the others remember what matters most when tragedy strikes close to home.
- DirectorIan SomerhalderStarsPaul WesleyIan SomerhalderKat GrahamStefan 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.
- DirectorPaul WesleyStarsPaul WesleyIan SomerhalderKat GrahamWhen 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.
- DirectorRob HardyStarsPaul WesleyIan SomerhalderKat GrahamMeanwhile 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.
- DirectorMichael A. AllowitzStarsPaul WesleyIan SomerhalderKat GrahamDespite 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.
- 2009–201741mTV-147.9 (1.1K)TV EpisodeDirectorMichael KarasickStarsPaul WesleyIan SomerhalderKat GrahamAs 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.
- DirectorPascal VerschoorisStarsPaul WesleyIan SomerhalderKat GrahamNo one can accept the loss of Damons humanity that Enzo hopes for too, Damon carelessly tries to prove everyone wrong.
- DirectorKellie CyrusStarsPaul WesleyIan SomerhalderKat GrahamWith 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.
- 2009–201742mTV-147.8 (985)TV EpisodeDirectorTanya HamiltonStarsPaul WesleyIan SomerhalderKat GrahamFaced 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.
- 2009–201742mTV-147.6 (917)TV EpisodeDirectorChris GrismerStarsPaul WesleyIan SomerhalderKat GrahamWhen 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.
- DirectorRashaad Ernesto GreenStarsPaul WesleyIan SomerhalderKat GrahamDetermined 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.
- DirectorMichael A. AllowitzStarsPaul WesleyIan SomerhalderKat GrahamStefan searches tirelessly for Damon and Enzo months after their mysterious disappearance.
- DirectorJulie PlecStarsPaul WesleyIan SomerhalderKat GrahamIn 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.
- DirectorMichael KarasickStarsPaul WesleyIan SomerhalderKat GrahamTired 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.
- DirectorGarreth StoverStarsPaul WesleyIan SomerhalderKat GrahamVampire 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.
- DirectorJeffrey G. HuntStarsPaul WesleyIan SomerhalderKat GrahamStefan 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.
- DirectorPascal VerschoorisStarsPaul WesleyIan SomerhalderKat GrahamStefan uncovers the reason behind Damon's dark descent following his experience in the Phoenix stone.
- DirectorPaul WesleyStarsPaul WesleyIan SomerhalderKat GrahamCaroline throws a baby shower for Alaric's twins, and the Salvatore brothers face the hallucinations caused by the Phoenix Stone.
- DirectorGeoffrey Wing ShotzStarsPaul WesleyIan SomerhalderKat GrahamIn the events following their mother's passing, Stefan and Damon try to engage in the holiday spirit.
- DirectorDeborah ChowStarsPaul WesleyIan SomerhalderKat GrahamDamon'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.
- 2009–201742mTV-148.2 (1.1K)TV EpisodeDirectorLeslie LibmanStarsPaul WesleyIan SomerhalderKat GrahamIt'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.
- DirectorDarren GenetStarsPaul WesleyIan SomerhalderKat GrahamAfter 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.
- DirectorChris GrismerStarsPaul WesleyIan SomerhalderKat GrahamDamon makes a decision that could ruin Lily and Stefan's deal; Alaric needs Bonnie's help with an artifact; Caroline discovers a shocking secret.
- DirectorTony SolomonsStarsPaul WesleyIan SomerhalderKat GrahamDamon and Stefan conspire to kill Julian, while Caroline struggles with the fact that she's pregnant with Ric's kids.
- 2009–201742mTV-148.5 (1.3K)TV EpisodeDirectorMichael A. AllowitzStarsNina DobrevPaul WesleyIan SomerhalderElena and Bonnie help Jo with last minute wedding preparations.
- DirectorKellie CyrusStarsPaul WesleyIan SomerhalderKat GrahamBonnie, Damon, and Alaric go through a tough shock with the Phoenix stone, while Caroline sent Stefan to spend the day with his ex, Valerie.
- 2009–201742mTV-148.8 (1.9K)TV EpisodeDirectorChris GrismerStarsNina DobrevPaul WesleyIan SomerhalderIn 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.
- DirectorMichael A. AllowitzStarsPaul WesleyIan SomerhalderKat GrahamIn 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.
- DirectorGeoffrey Wing ShotzStarsNina DobrevPaul WesleyIan SomerhalderStefan 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.
- 2009–201742mTV-147.8 (1.1K)TV EpisodeDirectorJesse WarnStarsNina DobrevPaul WesleyIan SomerhalderDamon 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.
- 2009–201742mTV-147.7 (1.1K)TV EpisodeDirectorLeslie LibmanStarsNina DobrevPaul WesleyIan SomerhalderDamon 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.
- DirectorJoshua ButlerStarsNina DobrevPaul WesleyIan SomerhalderElena and Damon enter the 1903 prison world to bring back his mother. Stefan intends to exact revenge on Caroline. Bonnie cannot forgive Kai.
- 2009–201742mTV-148.2 (1.5K)TV EpisodeDirectorPascal VerschoorisStarsPaul WesleyIan SomerhalderKat GrahamDamon 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.
- DirectorPascal VerschoorisStarsNina DobrevPaul WesleyIan SomerhalderElena 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.
- DirectorKellie CyrusStarsNina DobrevPaul WesleyIan SomerhalderElena 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.
- DirectorJulie PlecStarsNina DobrevPaul WesleyIan SomerhalderEverybody gathers for the funeral of Liz Forbes. Elena is worried Caroline isn't coping as well as everyone believes.
- DirectorIan SomerhalderStarsNina DobrevPaul WesleyIan SomerhalderStefan blames himself for Caroline turning off her humanity. Bonnie is angry with Damon for aligning himself with Kai. Sarah's life is in danger.
- 2009–201741mTV-147.9 (1.2K)TV EpisodeDirectorMichael A. AllowitzStarsNina DobrevPaul WesleyIan SomerhalderBonnie 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.
- DirectorChris GrismerStarsNina DobrevPaul WesleyIan SomerhalderElena 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.
- DirectorPaul WesleyStarsNina DobrevPaul WesleyIan SomerhalderAs 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.
- DirectorJoshua ButlerStarsNina DobrevPaul WesleyIan SomerhalderElena 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.
- 2009–201742mTV-148.1 (1.4K)TV EpisodeDirectorDarren GenetStarsNina DobrevPaul WesleyIan SomerhalderElena is forced to confront her problems; Liv and Tyler get closer; Damon finds a surprising clue that renews his hope.
- DirectorMichael A. AllowitzStarsNina DobrevPaul WesleyIan SomerhalderCaroline admits that she has feelings for Stefan. Bonnie and Damon find clues that make them think they might not be alone.
- 2009–201742mTV-147.9 (1.3K)TV EpisodeDirectorGarreth StoverStarsNina DobrevPaul WesleyIan SomerhalderElena 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.
- DirectorJeffrey G. HuntStarsNina DobrevPaul WesleyIan SomerhalderFour 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.
- DirectorMichael A. AllowitzStarsNina DobrevPaul WesleyIan SomerhalderWhen 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.
- 2009–201742mTV-148.5 (1.6K)TV EpisodeDirectorLeslie LibmanStarsNina DobrevPaul WesleyIan SomerhalderElena 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.
- DirectorKellie CyrusStarsNina DobrevPaul WesleyIan SomerhalderDamon and Bonnie are trying to come up with a way to come back from the otherside, while Stefan tries to help Elena start fresh.
- DirectorChris GrismerStarsNina DobrevPaul WesleyIan SomerhalderDamon'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.
- 2009–201742mTV-148.7 (1.3K)TV EpisodeDirectorChris GrismerStarsPaul WesleyIan SomerhalderKat GrahamA wedding is quickly planned in order for Damon and Stefan to lure a dangerous enemy out into the open.
- DirectorJoshua ButlerStarsNina DobrevPaul WesleyIan SomerhalderDamon 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.
- DirectorMichael A. AllowitzStarsNina DobrevPaul WesleyIan SomerhalderEnzo 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.
- DirectorPaul WesleyStarsNina DobrevPaul WesleyIan SomerhalderElena 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.
- DirectorPascal VerschoorisStarsNina DobrevPaul WesleyIan SomerhalderDamon tries to figure out how to make a disturbing confession to Elena.
- 2009–201743mTV-147.7 (1.3K)TV EpisodeDirectorDarren GenetStarsNina DobrevPaul WesleyIan SomerhalderHoping 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.
- 2009–201742mTV-147.9 (983)TV EpisodeDirectorPaul WesleyStarsPaul WesleyIan SomerhalderKat GrahamWhen 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.
- DirectorLance AndersonStarsNina DobrevPaul WesleyIan SomerhalderWhile Nadia remembers her centuries-long search for her mother, Stefan, Caroline and Matt come up with a desperate new plan to save Elena's life. For the second time, Bonnie and Jeremy must turn to Liv for help. Damon baits Tyler into a nasty confrontation, then takes off to seek revenge on Dr. Wes. Caroline and Tyler come to a new understanding. Finally, Bonnie learns of a terrifying secret that will threaten the lives of all her friends.
- DirectorMichael A. AllowitzStarsNina DobrevPaul WesleyIan SomerhalderAs 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.
- DirectorKellie CyrusStarsNina DobrevPaul WesleyIan SomerhalderDamon 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.
- DirectorChris GrismerStarsNina DobrevPaul WesleyIan SomerhalderBack to Katherine's early life 1490, Nadia helps her mom with a fighting plan.
- DirectorChris GrismerStarsNina DobrevPaul WesleyIan SomerhalderDamon is trapped by Dr. Wes, and realizes scary things about his past.
- DirectorKellie CyrusStarsNina DobrevPaul WesleyIan SomerhalderDamon 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.
- DirectorRob HardyStarsNina DobrevPaul WesleyIan SomerhalderAt Whitmore College, Elena and Caroline decide it's time to throw a big party, but their plans are interrupted when Jesse suddenly needs Caroline's help. At Elena's request, Damon comes up with an effective method to get Wes to answer his questions. At the party, Elena finds that she and Aaron have a lot in common, and Caroline grows more concerned about Jesse. Meanwhile, Katherine does a favor for Matt and manages to get through to Stefan, who is still struggling to overcome the events of the summer. Finally, Bonnie does her best to cope with her new reality, and Damon makes a terrifying discovery about a secret society.
- DirectorLeslie LibmanStarsNina DobrevPaul WesleyIan SomerhalderThe power of doppelgangers.... While Elena and Damon try to explain Amara's situation to Stefan, Dr. Wes Maxfield gives Katherine some deeply disturbing news. Nadia shows up at Caroline's dorm room searching for Katherine. After a surprising conversation with Amara, Jeremy and Bonnie share a glimmer of hope. Silas fails to keep a promise, causing Damon to turn to Tessa for help with his new plan, and Stefan makes a heartbreaking confession to Damon and Elena.
- DirectorIan SomerhalderStarsPaul WesleyIan SomerhalderKat GrahamStefan will find himself with a choice to make and his decision will determine the fates of everyone he cares about, especially Damon.
- DirectorMichael A. AllowitzStarsNina DobrevPaul WesleyIan SomerhalderDamon 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 (KENDRICK SAMPSON) better.
- DirectorJoshua ButlerStarsNina DobrevPaul WesleyIan SomerhalderA fellow Whitmore student named Jesse (KENDRICK SAMPSON) gives Elena some intriguing information about Professor Wes Maxfield (RICK COSNETT). Damon asks for help finding Stefan.
- DirectorJesse WarnStarsNina DobrevPaul WesleyIan SomerhalderWhen Elena and Katherine have the same dream that Stefan is in danger and desperately needs their help, they convince Damon to help them find Stefan. However, their plans are thwarted by a mysterious young woman named Tessa who seems to know everything about Stefan's history. In flashbacks to a distant time and place, Tessa reveals the shocking secrets in her past and what she has planned for the future. She also has a disturbing message for Damon about his own future. Silas forces an unwilling accomplice to help him search for Katherine, leading to a confusing and life-threatening situation for Matt. Finally, Silas reveals the reason he's determined to find Katherine, and Damon and Elena face a disturbing new reality.
- DirectorKellie CyrusStarsNina DobrevPaul WesleyIan SomerhalderOn campus, Elena is touched by a sad and secretive student named Aaron. Elena and Damon attend the Whitmore Historical Ball dressed as Anne Boleyn and Henry VIII. At the ball, Elena shares a dance with Dr. Maxfield, who has a disturbing message for her. Caroline's evening at the ball takes her from happiness to heartbreak. Meanwhile, Nadia reveals her surprising history to Katherine, and Damon tries to make a deal with Silas. But when Silas demands that Damon commit an unthinkable act, it leads to a violent confrontation.
- DirectorChris GrismerStarsNina DobrevPaul WesleyIan SomerhalderSeason finale: 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.
- DirectorJ. Miller TobinStarsNina DobrevPaul WesleyIan SomerhalderWhen 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.
- DirectorDarnell MartinStarsNina DobrevPaul WesleyIan SomerhalderThe Salvatore brothers ask for backup from a surprising source when Elena calls their bluff. Katherine is suspicious when Bonnie makes her an offer.
- 2009–201742mTV-148.3 (2.4K)TV EpisodeDirectorLance AndersonStarsNina DobrevPaul WesleyIan SomerhalderAs 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 (PAUL WESLEY).
- DirectorGarreth StoverStarsNina DobrevPaul WesleyIan SomerhalderRealizing 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.
- DirectorRob HardyStarsNina DobrevPaul WesleyIan SomerhalderSomeone 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.
- DirectorChris GrismerStarsNina DobrevPaul WesleyIan SomerhalderKlaus returns to his past in New Orleans and meets with his former protégé, Marcel (CHARLES MICHAEL DAVIS), a charismatic vampire with control over the city's inhabitants.
- 2009–201742mTV-148.0 (1.1K)TV EpisodeDirectorJeffrey G. HuntStarsPaul WesleyIan SomerhalderKat GrahamJust 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.
- DirectorChris GrismerStarsNina DobrevPaul WesleyIan SomerhalderDamon has an ugly run-in with a Hunter, Vaughn (CHARLIE BEWLEY - The Twilight Saga), and realizes he is one of the Five. Stefan admits his feelings about possibly becoming human.
- DirectorJesse WarnStarsNina DobrevPaul WesleyIan SomerhalderElena's new outlook has everyone concerned. Damon and Rebekah (CLAIRE HOLT) work together, but his unwanted advice catches her off-guard. Klaus tries to use Hayley (PHOEBE TONKIN).
- DirectorLance AndersonStarsNina DobrevPaul WesleyIan SomerhalderDamon and Rebekah (CLAIRE HOLT) learn an unexpected bit of recent history from Vaughn (CHARLIE BEWLEY). Bonnie reveals the rest of Shane's (DAVID ALPAY) plan.
- DirectorMichael A. AllowitzStarsNina DobrevPaul WesleyIan SomerhalderShane (DAVID ALPAY) leads an expedition to a desolate island, where he believes the secret of the cure lies hidden. Rebekah (CLAIRE HOLT) and Elena continue their bitter rivalry.
- DirectorDavid Von AnckenStarsNina DobrevPaul WesleyIan SomerhalderRebekah (CLAIRE HOLT) is back with a vengeance. Bonnie is uncomfortable when her father, Rudy Hopkins (RICK WORTHY - Supernatural), accepts the role of Interim Mayor.
- DirectorPascal VerschoorisStarsNina DobrevPaul WesleyIan SomerhalderIt's a winter wonderland in Mystic Falls. Plus, Professor Shane (DAVID ALPAY) reveals a piece of ancient history that leaves everyone speechless.
- 2009–201742mTV-148.3 (1.8K)TV EpisodeDirectorJesse WarnStarsNina DobrevPaul WesleyIan SomerhalderDamon and Stefan visit New Orleans in hopes of finding someone who remembers their last visit in 1942. MADELINE ZIMA (Californication) guest stars as one of Damon's former flames.
- DirectorJohn DahlStarsNina DobrevPaul WesleyIan SomerhalderJeremy 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, and Shane's responses push Bonnie to the edge of her powers. Elena negotiates with Klaus to keep Jeremy safe, but when danger suddenly appears from a totally unexpected enemy, Elena comes up with her own daring plan for Jeremy.
- 2009–201743mTV-148.3 (1.8K)TV EpisodeDirectorWendey StanzlerStarsNina DobrevPaul WesleyIan SomerhalderTerrifying hallucinations leave Elena shaken and confused and she makes a painful confession to Stefan. Matt gives Damon startling information about Professor Shane (DAVID ALPAY).
- DirectorChris GrismerStarsNina DobrevPaul WesleyIan SomerhalderStefan and Klaus form an uneasy alliance to try and contain the danger that Connor (TODD WILLIAMS) has unleashed. Professor Shane (DAVID ALPAY) works with Bonnie.
- DirectorJeffrey G. HuntStarsNina DobrevPaul WesleyIan SomerhalderAt the annual Miss Mystic Falls Pageant, Elena and Caroline give April (GRACE PHIPPS) advice, while Tyler and Hayley (PHOEBE TONKIN) work together on a secret project.
- DirectorJoshua ButlerStarsNina DobrevPaul WesleyIan SomerhalderAt 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.
- DirectorRob HardyStarsNina DobrevPaul WesleyIan SomerhalderStefan and Damon argue about what is best for Elena. Jeremy and Matt are surprised to see a girl they used to know, April (GRACE PHIPPS), enrolling at Mystic Falls High.
- DirectorJeffrey G. HuntStarsNina DobrevPaul WesleyIan SomerhalderCaroline struggles to save her mother. Damon comes up with a daring new plan. Jo and Kai prepare to merge, but Luke intervenes.
- DirectorLance AndersonStarsNina DobrevPaul WesleyIan SomerhalderElena learns confronting Rebekah (CLAIRE HOLT) can be dangerous. Tyler gets a surprise visit from Hayley (PHOEBE TONKIN - The Secret Circle), a werewolf who helped him with Klaus.
- DirectorJohn BehringStarsNina DobrevPaul WesleyIan SomerhalderDespite 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.