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1-50 of 81
- 2009–201742mTV-148.3 (2.4K)TV EpisodeAs 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).
- A fellow Whitmore student named Jesse (KENDRICK SAMPSON) gives Elena some intriguing information about Professor Wes Maxfield (RICK COSNETT). Damon asks for help finding Stefan.
- When 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.
- On 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.
- 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 (KENDRICK SAMPSON) better.
- Damon and Elena are skeptical of Silas's new goal; Tessa realizes she was outsmarted by Silas; after discovering a new consequence of becoming human, Katherine decides she needs a new place to stay; Bonnie is impressed with Jeremy.
- The 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.
- At 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.
- Damon is trapped by Dr. Wes, and realizes scary things about his past.
- Damon realizes Elena is in danger and enlists Stefan's help to find her. The brothers pay a visit to Aaron, and Damon shocks Stefan by revealing his first-hand knowledge of Aaron's family. In an attempt to stop Damon, Dr. Wes unleashes his secret weapon, forcing Damon to deal with a part of his past he thought was gone forever, as well as the consequences of his decades-long plan for revenge. Meanwhile, Elena is horrified by Dr. Wes' confessions about the dark history of Whitmore College and his own ultimate goal. Finally, a frantic Katherine turns to Matt for help, until she realizes that Nadia may be the one who can solve her problem.
- Back to Katherine's early life 1490, Nadia helps her mom with a fighting plan.
- 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.
- 2009–201743mTV-147.7 (1.3K)TV EpisodeHoping to help everyone move past recent traumatic events, Caroline convinces Elena and Bonnie to attend Whitmore College's "Bitter Ball" for broken-hearted students. Bonnie is intrigued with a fellow student named Liv, who appears to be dabbling in witchcraft. Tyler starts to worry about Matt's relationship with Nadia. After making a disturbing discovery, Stefan has a frustrating conversation with Damon and Enzo. Dr. Wes struggles to continue his research project with help from a new benefactor named Sloan. Still bent on revenge, Damon and Enzo resort to violence to convince Bonnie and Jeremy to help them, but their plan takes an unexpected and horrifying turn.
- As Damon's behavior escalates from destructive to deadly, Stefan begins to regret their last conversation and decides to track Damon down and intervene. For reasons of her own, "Elena" volunteers to come along. Dr. Wes enlists the Travelers to set a trap that will once again test Damon's friendship with Enzo. After a heart-to-heart talk with Nadia, Matt enlists Caroline and Tyler's help to protect Elena, leading to a violent confrontation. Later, when Stefan tries to comfort a dejected Caroline, their conversation leads to a horrifying realization.
- While 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.
- Damon tries to figure out how to make a disturbing confession to Elena.
- Bonnie has an unsettling encounter with Luke (CHRIS BROCHU), and learns more about his family history. The Travelers' leader, Markos (RAFFI BARSOUMIAN), arrives in Mystic Falls.
- Elena and Stefan start having dreams about an alternate version of their lives; The Travelers move in on Mystic Falls; Matt has a frightening encounter on the Other Side.
- Enzo holds Elena, Stefan and Bonnie hostage to uncover the truth about the love of his life. Markos performs a ritual to undo witch's magic.
- Damon and Caroline suspect Stefan and Elena of keeping a secret while they hide from the travelers, unaware of the dead man out for revenge. Meanwhile Matt, Jeremy and Bonnie help Tyler get rid of Julian.
- When Stefan and Elena escape from Markos' control, only to find themselves Stranded in a remote location, Stefan gets philosophical with Elena about her relationship with Damon. After their attempt to protect the doppelgangers goes badly, Liv and Luke come up with a dangerous new strategy. Damon recruits Matt and Jeremy to help him set a trap for Markos, who turns out to have a devastating surprise of his own. Bonnie finally admits to Caroline that she's been keeping the truth about the Other Side from everyone. Finally, while Bonnie searches desperately for a way to stop Markos, Caroline is witness to an unthinkable act of violence by one of the Travelers.
- Damon's plan causes a huge explosion in Mystic Falls, and everyone is caught up in the confusion, leaving a trail of heroism, sacrifice, relief and despair.
- Four months have gone by since the Other Side broke down and Bonnie and Damon were lost. Mystic Falls is still a supernatural-free area. Everyone is grieving in their own ways, and some worse than others.
- Damon and Bonnie are trying to come up with a way to come back from the otherside, while Stefan tries to help Elena start fresh.
- Caroline admits that she has feelings for Stefan. Bonnie and Damon find clues that make them think they might not be alone.
- Knowing she needs to come to terms with the loss of Damon, Elena turns to Alaric to help her move on with her life. Enzo convinces Caroline to join him as he tracks down a lead to get Damon and Bonnie back, but Caroline is shocked when they make an unexpected detour and uncover what Stefan has been up to. Meanwhile, Matt worries about Jeremy who is spending time with Sarah, a mysterious girl who has recently arrived in Mystic Falls. Elsewhere, Tripp, leader of the community protection program, makes an interesting confession to Matt about his connection to the town. Lastly, with the Other Side destroyed and gone for good, Damon and Bonnie reluctantly band together to uncover the mystery of where they are and how they are going to get back home.
- 2009–201742mTV-148.5 (1.6K)TV EpisodeElena 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.
- 2009–201742mTV-147.9 (1.3K)TV EpisodeElena 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.
- 2009–201742mTV-148.1 (1.4K)TV EpisodeElena is forced to confront her problems; Liv and Tyler get closer; Damon finds a surprising clue that renews his hope.
- Elena gets some hopeful news from Alaric and Stefan regarding the Gemini Coven; Tyler tries to help Liv and Luke after learning of disturbing plans the coven has for them; dinner takes a drastic turn for Jo; Kai makes a dangerous discovery.
- As Kai learns how to control his magic, he holds Elena captive; Caroline and Stefan go to North Carolina in search of a cure for Sheriff Forbes; Damon realizes Elena has been kidnapped.
- 2009–201741mTV-147.9 (1.2K)TV EpisodeBonnie 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.
- Elena and Damon enter the prison world to bring Bonnie home. Complications arise when Kai escapes and finds Liv. Stefan finds out the truth about Sarah.
- Elena and Jeremy reminisce about their past; Caroline and Stefan grow closer; Sheriff Forbes asks Damon for help with a case involving Elena's parents; Enzo lures Matt and Sarah into his plan.
- Everybody gathers for the funeral of Liz Forbes. Elena is worried Caroline isn't coping as well as everyone believes.
- Stefan blames himself for Caroline turning off her humanity. Bonnie is angry with Damon for aligning himself with Kai. Sarah's life is in danger.
- Caroline struggles to save her mother. Damon comes up with a daring new plan. Jo and Kai prepare to merge, but Luke intervenes.
- Elena is determined to celebrate Bonnie's birthday; after learning Stefan's secret, Enzo wants to interfere in Sarah Salvatore's life; Caroline struggles to cope with everything going on around her.
- 2009–201742mTV-148.2 (1.5K)TV EpisodeDamon 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.
- Elena 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-147.7 (1.1K)TV EpisodeDamon concocts a risky plan involving Lily to stop Caroline and Stefan from wreaking havoc; Elena re-evaluates her life as a vampire after learning that Jo is pregnant; Sarah turns the tables on Enzo; Tyler and Matt wind up in danger.
- Stefan concocts a plan to get Caroline to turn her humanity back on. Damon wrestles with what he should do with the cure. Enzo seeks answers.
- 2009–201742mTV-147.8 (1.1K)TV EpisodeDamon 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-148.5 (1.3K)TV EpisodeElena and Bonnie help Jo with last minute wedding preparations.
- 2009–201742mTV-148.8 (1.9K)TV EpisodeIn 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.
- 2009–201742mTV-148.0 (1.1K)TV EpisodeJust 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.
- 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.
- Damon makes a decision that could ruin Lily and Stefan's deal; Alaric needs Bonnie's help with an artifact; Caroline discovers a shocking secret.
- Bonnie, Damon, and Alaric go through a tough shock with the Phoenix stone, while Caroline sent Stefan to spend the day with his ex, Valerie.