Elena Gilbert och hennes bror Jeremy försöker komma över deras föräldrars bortgång. Elena är populär bland sina vänner och har högsta betyg i det mesta men har svårt för att dölja sorgen.
Två hundraåriga vampyrbröder återvänder till hemstaden Mystic Falls där övernaturliga varelser lever i hemlighet bland invånarna. Bröderna, den ene ond och den andra god, blir förälskade i samma flicka vilket leder till hetlevrad passion och annorlunda komplikationer.
Elena Gilbert och hennes bror Jeremy försöker komma över deras föräldrars bortgång. Elena är populär bland sina vänner och har högsta betyg i det mesta men har svårt för att dölja sorgen.
Elena åker till Salvatore huset för att prata med Stefan men stöter istället på Damon som ger henne en inblick i Stefans förflutna. Vicki åter minns attacken.
Elena bjuder Stefan och Bonnie på middag i hopp om att de ska fatta tycke för varandra men kvällen förstörs när Damon och Caroline plötsligt dyker upp.
Stefan tar med Elena till stadens årliga fest. Väl där berättar Damon för Elena om Salvatore familjen och Elena fylls omedelbart av tvekan och frågor som hon vill ställa Stefan.
Stefan har förtroende för sin plan att göra sig av med Damon och bestämmer sig för att dela med sig av sitt förflutna till Elena.
I tillbakablickar avslöjar Stefan för Elena hela Salvatores familjehistoria bland annat hur hans tvist med Damon startade. I nutiden tar Damon kontroll över Vickis framtid.
Bonnie överraskar Damon med sina förmågor och Elena ber Jeremy att sluta träffa Vicki. I hopp om att uppmuntra Vicki tar Matt med henne till skolans spökhus men kvällen går inte som planerat...
Stefan får ett överraskningsbesök av hans gamla klasskamrat Lexi och Caroline försöker få tillbaka Damons medalj från Bonnie.
Jeremy blir positivt överraskad av den nya mystiska historieläraren, Alaric Saltzman och Damon berättar för Stefan varför han bestämde sig för att återvända till Mystic Falls.
När Sheriffen Forbes berättar för Damon att det skett ännu en attack erbjuder han sig att leta upp mördaren. Han får senare reda på skakande information om familjerna som grundade staden.
Damon reser till Goergia för att träffa förra älskarinnan Bree. Stefan försöker hjälpa Bonnie att övervinna sina rädslor och erkänna sin styrka och Jeremy träffar en tjej som heter Anna.
Damon, Elena och Stefan går på skoldansen med 50-talstema där Damon får träffa Alaric. Stefan och Damon försöker lista ut vem den nya vampyrer i stan är och Stefan ger Elena smycken fyllda med Vervain som ska skydda henne och hennes familj.
Genom tillbakablickar minns Stefan och Damon händelser från förr som bland annat innefattar deras pappa, Guiseppe Salvatore. Elena hjälper Stefan och Damon att hitta en dagbok som en gång tillhörde en släkting till Elena.
Stefan hjälper Elena och Bonnie från fara och Jeremy frågar Anna om hon vill gå på en fest i skogen. Stefan, Damon och Elena hjälper Boonie och Grams att öppna en grav och blir chockade över deras upptäckt.
Matt och Caroline får sig en överraskning när Matts mamma plötsligt dyker upp i Mystic Falls. Elena och Stefan är oroliga över Damons plötsligt positiva beteende och Alaric upptäcker något från sitt förflutna.
Anna tar med sig en otippad gäst och hälsar på Damon. Elena och Stefan går på en obekväm dubbeldejt med Caroline och Matt.
Stefan tvingas ta ett otäckt beslut och Matt hoppas på att hans mamma ska stanna. Carolines bil har kollapsat och hon gör en fasansfull upptäckt som kommer att skrämma livet på hela stan.
För en gång skull är Stefan på festhumör. Samtidigt försöker Damon att lista ut varför Elenas morbror John Gilbert har återvänt.
Elena och Caroline deltar i samma skönhetstävling som Spencer Locke. John Gilbert gör sitt bästa för att skrämma Damon.
Elena får veta hur Damon och Stefan blev vampyrer. Pearl ryker ihop med John Gilbert och Jeremy och Anna lär känna varandra bättre.
När Isobel återvänder hem förvånas Alaric över att hon är så positiv. Hon kan inte vänta på att få träffa Elena.
Folk är på festhumör och det grejas och fixas till firandet av stadens jubileum. Trots att Damon och Alaric försöker hindra Johnathan Gilbert lyckas han sätta sin plan i verket och förstöra festligheterna.
Elena återvänder hem och får till sin fasa höra vad som har hänt Jeremy och Uncle John. På sjukhuset väntar Sheriff Forbes på att få höra om Caroline kommer att överleva bilolyckan.
Efter att ha blivit utskriven från sjukhuset går Caroline till karnevalen i Mystic Falls med sina vänner. Matt försöker berätta för Caroline om sina känslor, trots att hennes beteende förvirrar honom.
Elena, Damon and Alaric reser till Duke-universitetet för att studera Isobels forskning om övernaturliga fenomen eftersom de hoppas kunna förstå den mystiska familjen Lockwood.
Stefan vidtar drastiska åtgärder när han försöker ta reda på varför Katherine har återvänt till Mystic Falls - och han överväldigas av den information hon ger honom angående vad som hände år 1864.
Medan Stefan och Damon bråkar om hur familjen Lockwood ska hanteras lär sig Tyler mer om Mason och familjens förbannelse. Jeremy kommer närmare Lockwood-mysteriet genom att umgås med Tyler.
Katerine väljer ett nytt offer. Trots Elenas försök att hålla Jeremy trygg erbjuder han att hjälpa Damon och Alaric att handskas med Katerine. Sheriff Forbes och Caroline spenderar sällsynt kvalitetstid som mor och dotter.
Stefan och Damon har en ny plan för att handskas med Katerine på familjen Lockwoods maskerad. Katerine tar med sig sin gamla kompis Lucy till festligheterna.
Stefan och Damon kommer till Elenas undsättning och får samtidigt reda på ny och överraskande information om människor, vampyrer och en del händelser i det förflutna. Caroline gör vad hon kan för att underlätta för Tyler.
Elena utsätter sig för fara när hon söker efter sanningen om Katherines förflutna, och svar på hur hennes egna framtid kommer att se ut.
Elena kommer på en plan och lockar Rose för att få hennes hjälp, men när Rose upptäcker Elenas verkliga avsikter kallar hon in Damon för att få assistans.
Fullmånen närmar sig och Caroline hjälper Tyler att förbereda sig inför sin oundvikliga omvandling. Stefan och Katherine försöker psyka varandra medan Damon och Alarik är misstänksamma mot en mystisk besökare.
Stefan har sina egna åsikter om Elenas planer för framtiden. Damon försöker få Jules att berätta sanningen och ber samtidigt Elena att hålla ett öga på Rose, vilket leder till en farlig situation.
Elena, Damon och Jenna förvånas när Johnathan Gilbert kommer tillbaka till Mystic Falls. Caroline berättar för Stefan om sitt samtal med Tyler, och Stefan försöker att hjälpa den förvirrade Tyler.
Stefan och Elena planerar en romantisk helg i Gilberts stuga vid sjön, men det visar sig att någon har följt efter dem. Jules förklarar för Tyler vad sol och måne-förbannelsen innebär, men utelämnar en viktig detalj.
Stefan berättar för Elena om en mörk tid i sitt liv - och om hur en person oväntat förändrade situationen. Damon har för avsikt att få Elijah i ett ouppmärksamt tillstånd, och planerar därför en fest med Alaric, Jenna och Andie.
Elena, Damon och Stefan förstår att Katherines kunskaper om Mystic Falls historia kan hjälpa dem att överleva, även om de är trötta på hennes eviga manipulerande. Caroline hittar ett nytt sätt att få Matts uppmärksamhet.
Isobels oväntade besök är förkrossande för Jenna, vilket gör Elena och Alaric arga på John. Den hjärtekrossade Caroline vet inte alls vad hon ska ta sig till med Matt. På annat håll visar sig Stefan och Damon ha ett nytt hemligt vapen.
Skolan förbereder inför en skoldans med inspiration från 1960-talet, och Elena får obehagliga meddelanden från Klaus. Bonnie försäkrar Jeremy om att hon är stark nog att hjälpa Elena.
Damon och Stefan blir ursinniga när de får reda på att Elena, mot deras vilja, har format en ny allians för att besegra Klaus. Samtidigt är Stefan upptagen med att försvara den förvirrade och uppskrämda Jenna.
Damon är beredd att vidta extrema åtgärder för att hindra Klaus från att skada Elena, vilket leder till konflikt med Stefan, som har andra åsikter om hur hon bör försvaras.
Fullmånen är på väg och Elena gör sig redo för det som Klaus har planerat. Tyler står inför sin andra förvandling. De farliga händelserna intensifieras snabbt, trots en modig och oväntad insats.
I Mystic Falls ska man visa "Borta med Vinden" på stadens torg. Samtidigt blandas Damons minnen av Katherine från 1864, med verklighetens Elena i nutid. Stefan betalar ett dyrt pris när han försöker förhindra en tragedi.
Elena fyller 18 år och kämpar tillsammans med Damon för att ta reda på vart Stefan har tagit vägen. Klaus och Stefan följer i varulvens spår och Jeremy kan inte förstå varför han ständigt ser Vickis och Annas spöken.
Klaus försöker att verkställa en plan för att få större makt, men saker går inte som planerat. Alaric och Damon deltar tveksamt i Elenas jakt efter Stefan, men hennes plan kan komma att sätta Damon i fara.
Medan Stephan är i Chicago med Klaus träffar han en vampyr från sitt förflutna, som fortfarande är intresserad av honom efter att flera decennier har förflutit.
Klaus kontaktar Gloria, en häxa i Chicago, för att få reda på varför hans plan inte fungerar som väntat. Gloria lyckas pussla ihop en del av bilden, men behöver Stefans hjälp för att få full klarhet.
Trots allt som har hänt är Caroline fast besluten att Elena, Bonnie, Matt och Tyler ska få njuta av en traditionell 'Senior Prank Night' innan skolåret börjar. Men när objudna gäster dyker upp tar kvällen en dödlig vändning.
Elena, Matt, Bonnie och Caroline börjar sitt sista skolår och försöker samtidigt att handskas med den senaste tidens händelser. Tyler är lite väl nöjd med sin nya verklighet, medan Damon frustreras över den nya gästen i huset.
I Mystic Falls förbereder man sig inför en årlig traditionell högtid, och staden invaderas snart av de dödas andar. Efter ett mycket våldsamt möte med en förargad själ måste Bonnie förklara för Damon varför dessa spöken plötsligt har sådan makt.
Elena och Bonnie hjälper Alaric att försöka förstå sin senaste upptäckt. Elena och Rebekah har en maktkamp, men slutligen avslöjar Rebeckah sina familjehemligheter och delar med sig av sitt våldsamma förflutna.
Elena blir förvirrad när Rebekah berättar varför det är så viktigt att hon kommer till skoldansen. Matt och Caroline upprörs av Tylers beteende under kvällen. Klaus försöker att genomföra sin senaste plan.
Stefan har gömt likkistorna som innehåller Klaus familjemedlemmar, och Klaus varnar sin omgivning att ingen går säker förrän han får tag i Stefan och hittar sin familj.
Elena, Bonnie och Matt ordnar en överraskningsfest åt Caroline, även om hon egentligen inte vill fira sin 18-årsdag. Stefan och Damon är oense om hur de ska hantera Klaus och den obetänksamme Stefan sätter igång med sin livsfarliga plan.
Bonnie misstänker att hennes återkommande mardrömmar om Klaus likkistor kan komma att avslöja hur han kan bli mördad. Genom dessa drömmar återförenas Bonnie med sin mor Abby, som hon inte har träffat på 15 år.
Sheriff Forbes avslöjar upprörande information för Alaric och Elena om ett visst mordvapen. Damon och Stefan arbetar vidare med sin uppgift att mörda Klaus, och Stefan söker hjälp hos Bonnie och Abby.
Damon och Stefan följer med Elena till en formell fest i Klaus nyrenoverade villa. Även Caroline och Matt är bjudna till festligheterna. Under kvällen avslöjar Elena en plan som kan leda till att flera personer mister livet.
Elena får reda på hur tanklöst Damon har betett sig och blir frustrerad över att ingen av hennes vänner håller med om hur de ska hantera original-familjens interna maktkamp.
Morden i Mystic Falls påminner Damon om en liknande brottsvåg, hundra år tidigare. Under en tillbakablick reser Damon tillbaka till 1912 och minns den vackra vampyren Sage, som lärde honom allting hon visste om livet.
Vi är tillbaka i nutida Mystic Falls där Damon återförenas med Sage, hundra år efter att de först träffades. Under öppningsceremonin för Wickery Bridge förvånas Damon när han upptäcker att Sage har återvänt.
Damon och Stefan planerar att ta kål på Klaus med sitt nya vapen. Klaus och Rebekah övertalar Finn att samarbeta på deras plan att bryta förbindelsen när han återförenas med Sage.
Elena och Damon vill försäkra sig om att Jeremy är i säkerhet i Denver och kolla om hans särskilda förmågor kan hjälpa dem hitta information om gamla Original vampyr-led, så Jeremy kontaktar Rose.
Alaric får hjälp från oväntat håll på sin farliga färd, medan Damon och Meredith funderar över sitt nästa steg. Skoldansen tar en dödlig vändning och Damon och Stefan måste kämpa för att rädda livet på alla inblandade.
Bonnie kontaktar Abby för att hjälpa henne att utföra en livsfarlig förtrollning. Situationen börjar bli ohållbar och Elena är fast besluten att skydda Caroline.
Vi tar en återblick till Elenas liv när hon fortfarande var precis som andra flickor. Vi får även reda på hur det gick till första gången hon träffade Stefan och han räddade henne från att drunkna.
Elena awakens on the morning after the accident to find the thing she dreaded most has come true – she died with vampire blood in her system and now must go through the terrible transition to become a vampire…or face certain death. Stefan promises Elena that he and Bonnie will exhaust every possible way out of the situation, but Damon is furious with his brother for letting Elena die in the first place. Bonnie pays a terrible price for her attempt to change Elena’s fate, while Damon takes out his frustration and rage on Matt. In a rare moment of empathy, Rebekah is deeply touched by Stefan and Elena’s devotion to one another. Finally, Pastor Young and the Town Council members begin rounding up the vampires and their supporters, leading to an unexpected tragedy.
Elena tries to cope with the extreme highs and lows that are part of becoming a vampire, and Stefan and Damon almost come to blows while arguing about what is best for her. Damon decides to help Elena in his own way and asks her not to tell Stefan. A stranger, Connor Jordan, arrives in town and begins questioning Sheriff Forbes and Mayor Lockwood. Connor’s actions quickly convince Stefan that they are dealing with a dangerous vampire hunter. Jeremy and Matt are surprised to see a girl they used to know, April, has returned to town and is enrolling at Mystic Falls High. At a town gathering, Elena comes close to losing control until Caroline steps in to help her. Finally, Damon confides his feelings to an unexpected friend.
Connor continues his search to uncover the secrets of Mystic Falls and tries to convince Jeremy to work with him. With Dr. Fell’s help, Damon and Klaus question Connor, but the confrontation takes a lethal turn. Trying to keep her new life as normal as possible, Elena is determined to continue her senior year at Mystic Falls High with support from Matt and Caroline. Rebekah’s arrival at school makes it difficult for Elena to control her anger, but she learns that confronting Rebekah can be extremely dangerous. Later, Rebekah realizes how alone she is, and reaches out to April. Stefan takes Elena on a thrilling motorcycle ride in an effort to show her that life can still be fun. Tyler gets a surprise visit from Hayley, a werewolf who helped him through the ordeal of breaking his sire-bond to Klaus. Concerned about Elena, as well as his own emotions, Stefan turns to a sympathetic Caroline for advice.
Damon goes with Elena and Bonnie to visit Whitmore College, where Professor Shane is taking over the Occult Studies classes formerly taught by Bonnie’s grandmother. At a fraternity costume party, Damon takes advantage of the wild scene to give Elena a lesson in choosing a victim. Rebekah’s attempt to buy Matt’s forgiveness falls flat, but she is intrigued by unexpected news from Klaus. When Stefan questions Klaus about Connor’s motives, Klaus reveals a long-ago encounter with a powerful group of vampire hunters, but it’s Rebekah who delivers the information that stuns Stefan.
Stefan and Klaus form an uneasy alliance to try and contain the danger that Connor has unleashed on the town. When Connor takes Jeremy, Matt and April hostage at the Grill, Stefan and Damon have a serious disagreement about the best course of action, and Elena is again caught between the two brothers. The situation quickly turns violent when Klaus sends one of his hybrids, Dean to stand up to Connor. Caroline is surprised to find Hayley at the Lockwood mansion. Meanwhile, Professor Shane works with Bonnie to help her get past her fear and guilt.
Terrifying hallucinations leave Elena shaken and confused, causing her to make a dangerous mistake. After giving Stefan some very disturbing news about Elena, Klaus takes matters into his own hands. Professor Shane reveals a story of ancient witchcraft to Damon and Bonnie. With help from Klaus and Stefan, Jeremy begins a new chapter in his life. Finally, Elena makes a painful personal confession to Stefan, and Matt gives Damon startling new information about Professor Shane.
Caroline does her best to be there for Stefan and Elena in a tough time. Damon tries to convince Stefan to help him uncover Prof. Shane’s motives, but Stefan is intent on carrying out a different plan with Klaus. At the annual Miss Mystic Falls Pageant, Elena and Caroline give April advice on which dress to wear, while Tyler and Hayley work together on a secret project, and Damon confronts Prof. Shane with his suspicions. Alarmed by the vivid nightmares he’s having, Jeremy turns to Matt for help, but the situation escalates sooner than anyone expected.
When Stefan confronts Damon with a suspicion about Elena, Damon has no choice but to help Stefan investigate. Searching for answers, Damon and Stefan visit modern day New Orleans to see if they can find anyone who remembers the events of their last visit in 1942, including one of Damon’s former flames, Charlotte. Elena, Caroline and Bonnie share a girls’ night while the Salvatore brothers are out of town, and emotions run high when Elena delivers some shocking news. At Hayley’s urging, Tyler confronts one of Klaus’ hybrids, Kimberly, and the situation quickly escalates into violence. Finally, Damon is faced with a heartbreaking decision.
As a Winter Wonderland-themed party fills the streets of Mystic Falls, Stefan and Caroline find themselves at odds with Tyler over his plans for Klaus and his hybrids. When Caroline proposes a solution to their problem, Hayley finds a dramatic way to make it clear that she is not on board. Later, Klaus makes a discovery that leads to chaos and violence. Meanwhile, Elena and Damon retreat to the Gilbert Lake House to help Jeremy conquer some dangerous inner demons with the help of Bonnie and Professor Shane, who reveals a piece of ancient history that leaves them all speechless.
Appearing unexpectedly at Mystic Falls High, Rebekah wastes no time trying to force Stefan, Elena and Caroline to answer her questions about the search for a cure, leading to a bombshell piece of information from Elena. When Bonnie’s father, Rudy Owens, accepts the role of Interim Mayor, he makes it a priority to protect his daughter, who isn’t at all comfortable with the role he suddenly wants to play in her life. Professor Shane continues to encourage Bonnie to believe in her powers, but he soon finds himself in danger when he reveals too much to the wrong person. Later, Caroline does her best to comfort Tyler after a violent confrontation. Meanwhile, at the lake house, Damon and Matt train Jeremy, trying to raise his game as a hunter, but Klaus is impatient with their progress and intervenes to speed up the process.
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, 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.
When Rebekah turns down Klaus’ plea to stop Kol and protect Jeremy, Klaus turns to Stefan for help. After an angry confrontation with her father, Mayor Hopkins, over his unconventional approach to ending the violence in Mystic Falls, Bonnie has a frightening run-in with Kol, followed by an unexpected visitor. Klaus complicates the already tense feelings between Stefan and Damon by revealing a bit of Stefan’s personal life, then surprises Damon by asking for personal advice. Elena tells Stefan about her dangerous plan for Jeremy, leaving Stefan in a difficult spot. When the high school’s 1980s Decade Dance 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 off the coast of Nova Scotia, where he believes the secret of the cure lies hidden. On the trek to the island’s interior, Rebekah and Elena continue their bitter rivalry, Stefan does his best to keep the peace, and Damon accuses Shane of leading them into a trap. Bonnie and Jeremy try to figure out the message of the Hunter’s mark, while Shane reveals more of the legend of Silas and the witch Qetsiyah, along with his own personal history. Back in Mystic Falls, Tyler confronts Klaus, and Caroline is caught up in the violence that follows.
On the island, Damon has an ugly run-in with a Hunter named Vaughn, and realizes he is one of The Five. Stefan confesses his true feelings about the possibility of becoming human again to Elena. When a stunning new piece of information about the cure is suddenly revealed, it changes the stakes for everyone. Jeremy helps Bonnie recognize what is real and what is an illusion, and Shane is comforted by a woman from his past, Caitlin. Back in Mystic Falls, Caroline and Tyler find that their attempt to translate the code on the Hunter’s Sword is futile without help from Klaus, who has his own reasons for solving the puzzle.
When Stefan arrives back in Mystic Falls with Elena and Jeremy, Caroline is immediately worried about Elena’s state of mind. Stefan reaches out to Dr. Fell and Matt for help. Still on the island, Damon relays somber news to Rebekah, and is surprised at her reaction. Together, Damon and Rebekah learn an unexpected bit of recent history from Vaughn. Everyone is horrified when Bonnie reveals the rest of Shane’s plan. Finally, after Damon does his best to help her, Elena comes up with a plan of her own.
Elena’s new outlook has everyone concerned, leading Stefan and Damon to agree that going back to the normal routine of high school would be the best thing for her. Caroline is pleasantly surprised when Elena decides to rejoin the cheerleading squad, but her pleasure turns to shock when Elena’s behavior proves dangerous. Not giving up on their search for the cure, Damon and Rebekah work together until his unwanted advice catches her off-guard. Klaus tries to use Hayley to get the information he’s after and makes an intriguing discovery in the process. Meanwhile, a bored Elena throws a wild party and gets into an ugly fight.
Realizing that Elena needs some time away from Mystic Falls, Damon takes her to New York City, where he lived and partied hard in the 1970s. When Rebekah also shows up in New York, she’s impressed with Elena’s secret agenda. Flashbacks reveal Damon’s hedonistic life in the underground club scene and a complicated encounter with Lexi. Meanwhile, Caroline and Stefan try to convince Klaus that it would be in his own best interest to help them track Silas down, and Bonnie struggles to keep her grasp on reality and do the right thing.
Elena and Rebekah take off in search of Katherine and find themselves in a small town in Pennsylvania, where Elena has a surprising encounter with another old acquaintance -- Elijah. Stefan and Damon are both concerned about Elena’s state of mind and are determined to do what’s best for her, but she makes it clear that helping her will be difficult. Damon is not sure how to react when Stefan reveals his unexpected plan for the future. Meanwhile, in Mystic Falls, Klaus receives Caroline’s reluctant help and comes to a new understanding of Silas’ powers.
After making a decision that infuriates Klaus, Elijah proposes a life-changing challenge for Rebekah. Caroline finds that her carefully laid plans for the perfect Senior Prom night are disrupted by Elena, so she turns to an amused Klaus for a solution. Determined to get through to Elena, Damon and Stefan both attend the prom, but the evening begins to spiral out of control despite their efforts. When Elena suddenly lashes out in a way no one could have predicted, Matt turns to Rebekah for help. Finally, Bonnie makes a terrifying discovery, and Klaus receives a message that could change everything.
Acting on a mysterious tip that a plot is brewing against him in New Orleans, Klaus makes a trip to the town he and his family helped build. Klaus’ questions lead him to a reunion with his former protégé, Marcel, a charismatic vampire who has total control over the human and supernatural inhabitants of New Orleans. Determined to help his brother find redemption, Elijah follows Klaus and soon learns that Hayley has also come to the French Quarter searching for clues to her family history, and has fallen into the hands of a powerful witch named Sophie. Meanwhile, in Mystic Falls, Damon and Stefan continue with their plan for Elena, while Katherine reveals a surprising vulnerability to Rebekah and asks her to deliver a message.
Damon and Stefan try a brutal new approach to provoke Elena into turning her humanity back on, and Caroline is frustrated when her attempt to intervene backfires. When Elena figures out a way to call the Salvatore brothers' bluff, they call for backup from a surprising source. Matt gives Rebekah some unsolicited advice on her life choices, and she tries to help him in return. Caroline has a confusing and dangerous encounter with Klaus, and Katherine is suspicious when Bonnie makes her an offer that she promises will benefit them both.
As Graduation Day approaches, Caroline tries to distract Elena by focusing on simple tasks like sending out announcements, but Elena won't be swayed from her new obsession. Sheriff Forbes calls Damon and Stefan to the hospital, where someone has been attacking patients. Still trying to force Katherine to help her, Bonnie refuses to give up on her plan to defeat Silas. As a violent wind storm causes a power outage in Mystic Falls, ghosts suddenly appear - some with good intentions and some bent on revenge.
On Graduation Day, Mystic Falls is overrun with ghosts intent on settling old scores and fulfilling their supernatural destinies. Damon’s life is in danger after a ghostly encounter, while Matt and Rebekah join forces to battle a ghost determined to find the cure. As everyone gathers for the graduation ceremony and the ghosts converge, help comes from an unlikely hero. Caroline receives a touching and unexpected graduation present, and Bonnie’s plan leads to the closing of the veil. Elena makes a decision about the Salvatore brothers and faces an epic confrontation with Katherine. Finally, 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.
Silas announces his new goal to Damon and Elena. Tessa tells Stefan about her next move. Katherine discovers an unexpected consequence of being human and realises she needs a new place to stay. Bonnie is touched by Jeremy's determination to stand by her. Damon is stunned when he learns the secret to Tessa's plan.
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.
After spending the past four months coping with the loss of Damon in an unconventional and potentially dangerous way, Elena has returned to Whitmore College for the start of sophomore year. Unable to move on, Caroline is desperate to find a way to reverse the anti-magic spell the Travelers have put over Mystic Falls and grows frustrated when her calls to Stefan go unanswered. Tyler, who is human once again, has a run-in at a football tailgate that tests his ability to control his anger, while Matt worries that Jeremy is dealing with the loss of Bonnie in a self-destructive way. Alaric, who is struggling to adjust to his new life as a vampire, finds himself in an awkward situation when he meets Jo, a beautiful doctor at the university hospital. Last, while everyone believes Stefan is off tracking a lead to get Damon and Bonnie back, Elena is shocked when she learns the truth of what he has really been up to.
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.
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.
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.
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 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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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. 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.
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.
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.
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.
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.
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.
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 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.
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.
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.
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.
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 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.
In the aftermath of his brother's fateful decision, Stefan awakens to find himself thrown into a life or death situation with only his basic instincts to rely on. With time working against him, he sets off on a journey of survival while forced to confront a lifetime of irreversible damage Damon has done to their relationship. Meanwhile, desperate to save his brother, Damon follows an unusual lead he has come across, while Matt sends Valerie to Dallas to enlist Alaric's help in the search for Stefan. Finally, when Rayna discovers the emergence of a new threat, she sets off on her own mission to find Stefan before the others do.
Determined to capture an escaped vampire named Ambrose, who may be the key to getting Stefan back safely, Damon heads to Memphis with Alaric in tow. However, reluctant to step back into his former vampire hunting ways, Alaric makes his unwillingness to participate clear, while revealing the truth about the past three 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.
When Damon's risky attempt to save Bonnie takes an unexpected turn, the consequences of his actions forces everyone to band together to help her pull through. Meanwhile, when a new threat leaves Caroline's life in jeopardy, Stefan makes a rash decision that ultimately forces them to face the fallout from their relationship. Elsewhere, Enzo tries to hold it together as he painfully watch Bonnie in the fight of her life, while Matt takes matters into his own hands to save one of his closest friends.
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.
Months after Damon and Enzo mysteriously vanished from the Armory vault, Stefan tirelessly pushes forward with their search, while Bonnie struggles holding onto hope that they will be found. Meanwhile, a dangerous encounter with an unexpected visitor leaves Caroline and Alaric fearing that someone – or something – may be targeting their family. Finally, after following some mysterious clues, Stefan realizes that whatever has a hold of his brother may have a more damaging grip over him than he could have ever imagined.
After learning that someone from Stefan’s past may be Damon and Enzo’s next target, Stefan, Bonnie and Caroline head to North Carolina. There, Bonnie takes drastic measures in an attempt to break Enzo free of whatever has a hold over him. At the Armory, Alaric and Georgie stumble upon a mysterious symbol that may be related to the supernatural force controlling Damon and Enzo. Finally, Caroline gets an unexpected surprise from Stefan.
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.
Spiraling down a dangerous path of self-destruction, Damon’s latest actions prove he may be beyond the point of return. Unwilling to give up on his brother, Stefan is forced to make a gut-wrenching decision that threatens to change their relationship forever. Elsewhere, Bonnie gets advice from Caroline on how to break through to Enzo, while Matt attempts to decipher a mysterious box of messages that he’s received. Finally, after tragedy strikes close to home, Stefan and the others are forced to remember what matters most to them.
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.
Stefan and Damon return to Mystic Falls at Sybil’s request as she is still in search of the historical artifact. Bonnie returns from Paris wearing a vile of Enzo’s blood making Caroline, wonder if she will become a vampire. Stefan, Damon, Caroline, Bonnie and Enzo all attend the Miss Mystic Falls pageant where Sybil continues to taunt Damon with memories of Elena.
Sybil enacts revenge on Damon by putting him in a catatonic state. Caroline and Bonnie enter Damon’s mind and run into familiar faces from the past, only to discover Stefan is the key to Damon’s fate. It’s a race against time for the bell as both Sybil and her sister Seline jockey for its control.
Cade returns to Mystic Falls and presents Damon and Stefan with additional assignments, each with unthinkable consequences. Even with tension growing in their friendship, Caroline and Matt do their best to protect the town’s residents from Cade’s appetite for their souls. Bonnie and Enzo hit the road on a romantic trip, taking the bell with them in hopes to keep it safe.
In order to save Stefan’s soul, Damon makes a deal with Cade to retrieve the Maxwell journal. Alaric and Matt refuse to hand the journal over as it may contain the key to destroying Cade. Caroline desperately tries to connect with Stefan before Cade goes through with his plan.
Damon and Alaric come face to face with an old enemy after they obtain a weapon that may be able to destroy Cade. Stefan is held captive by a surprising acquaintance and is forced to confront a dark secret from his past. Meanwhile, Caroline and Matt try to keep Stefan’s violent history from destroying him. Cade focuses his attention on Bonnie and digs deep into her mind.
Damon and Stefan must join forces against Cade in order to save Elena’s casket. Meanwhile, Caroline and Alaric deal with their daughters’ burgeoning magical powers.
A wedding is quickly planned in order for Damon and Stefan to lure a dangerous enemy out into the open. This looming threat puts the fate of Mystic Falls in eminent danger and must be destroyed.
With the fate of Mystic Falls at stake, Stefan and Damon must fight their greatest enemy for one last battle.
Release 2009-09-10
USA