Season 5 I Know What You Did Last Summer S5, Ep1 3 Oct. 2013 I Know What You Did Last Summer 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 (PAUL WESLEY). True Lies S5, Ep2 10 Oct. 2013 True Lies 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. Original Sin S5, Ep3 17 Oct. 2013 Original Sin 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 ... For Whom the Bell Tolls S5, Ep4 24 Oct. 2013 For Whom the Bell Tolls 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. Monster's Ball S5, Ep5 31 Oct. 2013 Monster's Ball On campus, Elena is touched by a sad and secretive student named Aaron (recurring guest star SHAUN SIPOS - Melrose Place, Final Destination 2). 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 (recurring guest star RICK COSNETT), who has a disturbing message for her. Caroline's evening at the ball takes her from happiness to heartbreak. Meanwhile, Nadia (recurring guest star OLGA FONDA) reveals her surprising history to Katherine, and Damon tries to make a deal with Silas. ... Handle with Care S5, Ep6 7 Nov. 2013 Handle with Care Silas happily announces his new goal to Damon and Elena, but they are skeptical when he promises to accomplish one important task in return for their help. Tessa (recurring guest star JANINA GAVANKAR) confidently tells Stefan about her next move, then realizes that Silas has managed to outsmart her. A desperate Katherine discovers a new and unexpected consequence of becoming human again, and realizes she needs a new place to stay. In exchange for a spot in the dorm room, she offers to show Caroline how to get answers from Dr. Maxfield (recurring guest star RICK ... Death and the Maiden S5, Ep7 14 Nov. 2013 Death and the Maiden The power of doppelgangers.... While Elena and Damon try to explain Amara's (played by series star NINA DOBREV) situation to Stefan, Dr. Wes Maxfield (recurring guest star RICK COSNETT) gives Katherine some deeply disturbing news. Nadia (recurring guest star OLGA FONDA) 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 (recurring guest star JANINA GAVANKAR) for help with his new plan, and Stefan makes a ... Dead Man on Campus S5, Ep8 21 Nov. 2013 Dead Man on Campus At Whitmore College, Elena and Caroline decide it's time to throw a big party, but their plans are interrupted when Jesse (recurring guest star KENDRICK SAMPSON) suddenly needs Caroline's help. At Elena's request, Damon comes up with an effective method to get Wes (recurring guest star RICK COSNETT) to answer his questions. At the party, Elena finds that she and Aaron (recurring guest star SEAN SIPOS) 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 ... The Cell S5, Ep9 5 Dec. 2013 The Cell Damon is trapped by Dr. Wes, and realizes scary things about his past. Fifty Shades of Grayson S5, Ep10 12 Dec. 2013 Fifty Shades of Grayson 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, ... 500 Years of Solitude S5, Ep11 23 Jan. 2014 500 Years of Solitude Back to Katherine's early life 1490, Nadia helps her mom with a fighting plan. The Devil Inside S5, Ep12 30 Jan. 2014 The Devil Inside 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. Total Eclipse of the Heart S5, Ep13 6 Feb. 2014 Total Eclipse of the Heart Hoping 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 (recurring guest star PENELOPE MITCHELL - Hemlock Grove), who appears to be dabbling in witchcraft. Tyler starts to worry about Matt's relationship with Nadia (recurring guest star OLGA FONDA). After making a disturbing discovery, Stefan has a frustrating conversation with Damon and Enzo (recurring guest star MICHAEL MALARKEY). Dr. Wes (recurring guest ... No Exit S5, Ep14 27 Feb. 2014 No Exit 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. Gone Girl S5, Ep15 6 Mar. 2014 Gone Girl 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. While You Were Sleeping S5, Ep16 20 Mar. 2014 While You Were Sleeping When Stefan tries to explain recent events to a very sick Elena, her first instinct is to call Damon. At the same time, Damon is trying to figure out how to make a disturbing confession to Elena. While going through Dr. Wes' files, Caroline discovers a frightening secret, and is surprised when Enzo (recurring guest star MICHAEL MALARKEY) appears, claiming to have the solution everyone is searching for. At Enzo's insistence, Caroline asks Stefan to meet her at a mysterious location where they are joined by a group of Travelers, including Sloan (recurring guest star ... Rescue Me S5, Ep17 27 Mar. 2014 Rescue Me 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. Resident Evil S5, Ep18 17 Apr. 2014 Resident Evil Both Stefan and Elena are suddenly having unsettling dreams of an alternate version of the life they might have had together. Bonnie has a disturbing encounter with Grams, who warns her about frightening changes on the Other Side. Enzo gives Damon unwanted relationship advice, then admits he is searching for a woman he loved decades before while he was held captive by the Augustines. Liv enlists Matt, Jeremy and Tyler to help track the Travelers and keep them from taking control of Mystic Falls. Bonnie is hurt and angry when she learns that Jeremy is working with Liv ... Man on Fire S5, Ep19 24 Apr. 2014 Man on Fire 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. What Lies Beneath S5, Ep20 1 May 2014 What Lies Beneath 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. Promised Land S5, Ep21 8 May 2014 Promised Land 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 ... Home S5, Ep22 15 May 2014 Home 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.