Season 5 ends with Damon trying to stop the disintegration of the Other Side. Meanwhile, Elena takes matters into her own hands and demands that Liv and Luke help her; and Markos uses violence against Tyler/Julian to prove that Mystic Falls is under the control of the Travelers.moreless
Stefan and Elena become stranded in a remote location, after escaping from Markos, and he gets philosophical about her relationship with Damon. Liv and Luke develop a new plan after their attempt to protect Stefan and Elena goes awry. Meanwhile, Damon, along with Matt and Jeremy, sets a trap for Markos. Bonnie admits to Caroline 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.moreless
Tyler reveals that Markos' plans to break the witches curse isn't without its dangers to Elena and Stefan. So Damon takes Stefan and Elena to a cabin, once owned by Caroline's dad, to keep them safe, and then he devises a parlor game to get them to reveal a secret they've been hiding. At the cabin, a spirit uses violence and fire to let them know it is there. Matt's charged with getting information from one of the Travelers. Meanwhile, Bonnie keeps Jeremy in the dark regarding the truth about the Other Side, in spite of Grams warnings.moreless
Elena obsesses over the state of her relationship with Damon. Enzo, through flashbacks to election night in 1960, learns what happened to his long-lost love. When he enlists Liv and Luke's help, things take a bad turn. Damon's attempts to calm Enzo down results in a confrontation between Enzo and Stefan. Bonnie deal with changes happening on the Other Side. Jeremy and Matt admit to Damon that the Traveler knife is missing. Markos enlists Sloan's help in a ritual designed to break an ancient curse against the Travelers. Tyler finds himself forced to play a risky part in the ritual.moreless
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 is angry when she learns that Jeremy is working with Liv. Matt, Tyler and Jeremy help Liv keep track of the Travelers who plan to take over Mystic Falls. Matt has a terrifying encounter with inhabitants of the Other Side. Luke shows up and tells Damon, Elena and Enzo what he knows about Markos. Damon finds Markos and is both pleased and concerned about what he hears.moreless
Caroline and Enzo make a trip to Atlanta to find a recently revealed doppleganger. Enzo tells Caroline about his past. When Damon and Elena find out about Jeremy's bad behavior at school after a parent-teacher meeting, Damon lets Elena in on some disturbing news about Jeremy's personal life. Bonnie come across Luke and finds out more about his family history. Jeremy makes a deal with Liv after she tells him about the Travelers' next move and shows him how substantial her power has become. Caroline and Stefan share a special moment. The leader of the Travelers, Markos, makes an appearance.moreless
When Elena wakes, Stefan tries to fill her in on what has happened. Caroline finds a terrifying secret in Dr. Wesley's files just as Enzo shows up claiming to possess the solution. Caroline calls Stefan and asks him to meet her and Enzo in an mysterious location. When they get there, a group of Travelers lets them know something new about the importance of doppelgangers. Elena runs into Luke on campus who seems to know her. Rather than take him up on his suggestion to go on a drinking binge, she sends him off to find Bonnie and Liv. When Damon finally gets around to filling Elena in on his recent activities, they come to a new agreement about their relationship.moreless
Elijah undertakes Klaus' royal responsibilities and attempts to restore peace in the kingdom as the latter tries to distract himself. Hayley finds that Sabine was honest while a desperate and confused Marcel prepares to plot against the new powers that be.moreless
Stephen is still walking a fine line with his ULTRA partner Hillary who continues to question his loyalties.
When ULTRA and The Tomorrow People both learn of a breakout using her powers to benefit humans both sides seek her out to join their cause.
Meanwhile Morgan takes a risk and betrays Jedikiah's trust to help The Tomorrow People but Jedikiah learns something from her that is an even bigger surprise.
Even as Nadia is going back over the memories of her centuries long search for Katherine, Stefan, Caroline and Matt figure out a new plan to save Elena's life. Jeremy and Bonnie need Liv's help again. Damon is determined to get revenge on Dr. Maxfield. Caroline and Tyler work out a new understanding. Bonnie discovers a horrifying secret that endangers her friends.moreless
Julian returns with a vengeance but when he's caught by ULTRA he is forced to strike a deal that could cost him and Stephen their lives.
John disobeys Cara's orders again when he learns Julian has discovered the location of The Tomorrow People's lair.
Meanwhile still plagued by nightmares from her near death experience Astrid turns to John for comfort and support.
Since Dr. Wes injected Damon with the serum his behavior has gone from bad to worse. Stefan feels bad telling Damon never to return to Mystic Falls so he sets out to find him with Elena tagging along. Once again Dr. Wes asks the Travelers for help when he decides to test the friendship between Damon and Enzo. Matt recruits Caroline and Tyler to help protect Elena ending with a violent confrontation. As Stephan later tries to console unhappy Caroline, their talking leads to a shocking realization.moreless
After receiving some shocking news Stephen attempts to restore order in both his worlds by striking a deal with Jedikiah.
Cara and Russell contend with a new break-out and must also deal with an ULTRA trap.
Meanwhile Jedikiah is closer to developing a secret technology that could change his future.
Whitmore College holds its annual "Bitter Ball" for broken-hearted students, which Caroline persuades Elena and Bonnie to attend. Bonnie meets up with Liv who seems to be playing her hand at witchcraft. Matt's relationship with Nadia bothers Tyler. Stefan speaks to Damon and Enzo after making a troubling discovery. Dr. Maxfield gets a new benefactor for his struggling research project. Damon and Enzo use violence to induce Bonnie and Jeremy to help them with their revenge plans but things don't go as planned.moreless
Stephen is upset with Jedikiah for going back on his word, forcing him to face The Founder.
In order to protect Astrid, Stephen must make a deal to bring in a powerful break-out and elsewhere John clashes with Cara which forces her to issue a harsh punishment.
Nadia has figured out a way to keep Katherine permanently in Elena's body but first she needs to find Katherine's body which has mysteriously disappeared. Enzo comes to Damon with a grisly present and wants them to carry out an act of revenge but Damon tries had to do the right thing. Matt throws a party at which Caroline makes a stunning admission to Elena. Caroline's confession forces her then to face the consequence of her actions with Stefan and Tyler. Aaron decides to start a new life. When Elena finds herself in a life threatening position, she doesn't have much time to figure out how to save herself.moreless
Stephen feels uneasy about fellow ULTRA trainee, Hillary, who has her own secret agenda. After his mother insists the family go camping with Peter, Stephen asks John and Cara to ensure everything is okay with Astrid while he's gone.
With her impending death, 500-year-old Katherine reminisces about her life and the night she gave birth in 1490. Stefan informs Elena, Caroline and Bonnie that Katherine doesn't have long to live. Damon, Matt and Jeremy talk about Katherine's infamous moments. Stefan and Elena are forced to help Nadia save her mother. Caroline indulges in some scandalous behavior. Katherine and Elena share a moment of bonding.moreless
Stephen and his fellow ULTRA trainees are given a test by Jedikiah to determine their worthiness as Agents but not everyone is happy to work as a team.
Cara is faced with a visitor from her past and John works with a new breakout while Russell is sent on a dangerous recon mission that could force a clash between different groups of Tomorrow People
Davina loses control her powers and becomes violently ill and sends shockwaves, winds and rainstorms through the French Quarter. Elijah approaches the Sophie for answers and is informed that the Harvest Festival needs to be completed to save Davina. Hayle angers Elijah when she comes clean to about her role in Sophie's plan to complete the Harvest by consecrating Celeste dubois’s remains. Meanwhile Marcel takes Davina into hiding to prevent the Harvest ritual from being completed.
Damon asks for Stefan's help to find Elena. The brothers visit Aaron and Stefan is shocked of what Damon knows. Dr Wes is trying to stop Damon and thus releases a secret weapon, forcing Damon to face his past. Dr Wes confesses information to Elena about the history of Whitmore College as well as his goal. Katherine turns to Matt for help and she realizes that the solution to her problem may be Nadia.moreless
When John finds himself in a dangerous situation Stephen finds he is unable to help without revealing his duplicity to ULTRA. Also not satisfied with the answer he discovered about his father's death Stephen decides to take drastic action to find the truth with help from his fellow Tomorrow People.
Cara and Russell negotiate a trade with Jedikiah which ultimately makes Jedikiah take a big risk.
Stefan helps Katherine in order to deal with his pain until Caroline finds another way. Elena tries to fix things with Caroline and gets very concerned about Damon that she asks Aaron for help. Damon reveals aspects of his dark life to Elena and she tells him what she has just learnt about her family. Aaron takes a desperate path after a conversation with Dr. Wes.moreless
Stephen is determined to uncover what he hopes is the key to finding his father, and crafts a plan with The Tomorrow People that involves getting inside Jedikiah’s head. Meanwhile, Cara and Russell encounter an uninvited visitor in the subway tunnel base.
Stephen takes a risky opportunity and snoops around ULTRA.
Marcel is surprised when Klaus reveals him things about his past. Cami tries to understand what some messages she found mean and she finds out information about Klaus' past. The human factions decide to take action which lead to violence. Hayley learns of a plan to harm the werewolves in the bayou, so she asks for Elijah's and Rebekah's assistance. They run into Eve, another werewolf, who shares shocking information.moreless
Rebekah has a difficult decision to make and she addresses Father Kieran for help. Elijah and Klaus quarrel and Elijah needs to face the consequences of that. Hayley supports him, but she is distracted by someone who can can give her information about her past. Cami tries to depict a message. Marcel finds information about Klaus that upset him.moreless
Elena and Caroline decide to throw a party, but they are interrupted when Jesse requests Caroline's help. Damon gets information from Wes when Elena asks him to. At the party Elena finds out she is a lot like Aaron and Caroline is more and more concerned about Jesse. Katherine does a favor to Matt and helps Stefan coping with the events of the summer. Bonnie tries to deal with how things currently are and Damon makes a discovery about the secret society.moreless