A century after their first encounter, Damon and Sage meet again at the ceremony to kick-off the restoration of Wickery Bridge. Damon is surprised to learn the reason Sage has returned, and pleased when she devises an unusual method to help him figure out what Rebekah is up to. Abby is having a hard time adjusting to her new reality, despite Bonnie and Caroline’s efforts to help. When Damon informs Elena of Stefan’s latest struggles, she reaches out to Stefan to help her save a friend in danger, in hopes that it will help bring Stefan even closer to his humanity. Finally, when Damon discovers a new secret weapon, he lets Stefan in on the news.

The present-day murders in Mystic Falls remind Damon of a similar crime spree a century earlier. In flashbacks to 1912, Damon recalls a beautiful vampire, Sage, who showed him a whole new way to exist. Sheriff Forbes warns Damon not to get involved in her investigation, but Damon is convinced she’s going after the wrong suspect. Elena and Matt resort to breaking and entering in their search for evidence to prove Dr. Fell is a murderer. For reasons known only to her, Rebekah, becomes interested in locating one of the town’s oldest landmarks. Finally, Elena comes to a new understanding of the path her life has taken, and Damon makes an emotional confession to Stefan.

After starting her day with a startling discovery of Damon’s latest indiscretion, Elena is frustrated to find that none of her friends agree with her on how they should react to the Original family’s internal power struggle. Once again caught up in the destiny of the Bennett witches, Bonnie and Abby find themselves playing a part in a ritual to appease the spirits of nature. When Elijah gives Damon and Stefan a dangerous ultimatum that puts Elena in danger, they turn to Alaric and Meredith for help with a plan that leads them to a terrible choice.

Elena is surprised to receive an invitation to a formal ball, and when Damon and Stefan hear the party is being hosted at Klaus’s newly renovated mansion, they both insist on attending the event with her. Caroline and Matt also receive invitations to the ball from unexpected admirers. At the elegant party, Elena learns of a horrifying plan that could lead to numerous deaths and she must decide who she can trust with her new information. Caroline discovers a side of Klaus no one would have suspected. Finally, after an evening of violence and dashed hopes, Damon finds a new way to cope.

Sheriff Forbes delivers some disturbing news to Alaric and Elena about the weapon used in a recent murder. In the Salvatore brothers’ escalating quest to kill Klaus, Stefan turns to Bonnie and Abby, while Damon reaches out to an old acquaintance for help in setting up an elaborate plan. Intent on a plan of his own, Klaus hosts a strange dinner party, where he reveals another story from his family’s violent past until an unexpected guest brings the party to an end. Meanwhile, Caroline is heartbroken when she is unable to stop a tragedy from unfolding.

Bonnie believes her recurring dreams about Klaus’ coffins will tell her how he can be killed. The dreams also lead Bonnie to a reunion with her mother, Abby, whom Bonnie hasn’t seen for 15 years. At Abby’s remote farmhouse, Bonnie and Elena meet Jamie, the young man Abby took in years earlier. Bonnie’s sudden appearance catches Abby off-guard, but she does her best to explain the past. Tyler turns to an unexpected ally in his quest to regain his free will. Damon is intrigued by Alaric’s new friend, Dr. Fell, and Klaus continues his bitter negotiations with Stefan over control of the coffins containing his family members.

Although Caroline is in no mood to celebrate her 18th birthday, Elena, Bonnie and Matt surprise her with a small party in an unusual location. Damon and Stefan disagree on the best way to handle Klaus , and a reckless Stefan decides to test his theory by taking things to dangerous extremes. Bonnie is concerned when Elena tells her about Jeremy’s new plans. At a Founder’s meeting, Alaric once again runs into Dr. Fell, who is in the middle of an argument with her ex-boyfriend, the medical examiner. Tyler refuses to go along with Klaus’ latest demand, and is surprised when Klaus seems to accept his decision.

Stefan has hidden the coffins containing the bodies of Klaus’ family, and Klaus quickly turns to violence to convince Damon and Elena that no one will be safe until he finds Stefan and gets his family back. Tyler continues to make the most of his new abilities as a hybrid, but he has to face the disturbing consequences of his actions as well. After a terrifying incident, Elena and Alaric grow increasingly concerned about Jeremy’s attitude and, ultimately, his safety. Alaric meets the beautiful Dr. Fell, who is intrigued with his amazing ability to heal. While trying to strike a deal with Klaus, Elena delivers news that truly shocks him.

On the night of the Homecoming dance, Rebekah opens up to Elena about why the evening is so important to her, leaving Elena with conflicting emotions. Caroline and Matt are both shocked at Tyler’s behavior throughout the evening. The night takes a surreal turn when Klaus puts his latest plan into action. Determined to outsmart Klaus, Damon enters into a dangerous partnership, leading to a terrifying turn of events.

With help from Elena and Bonnie, Alaric tries to decipher the meaning behind his recent discovery Elena and Rebekah engage in a mean-girl power struggle, until Rebekah finally reveals some of her family’s ancient secrets and the violent past she shares with Klaus and Elijah. Damon tries a reckless new approach to make a breakthrough with Stefan, and they’re both surprised by an unlikely ally.

As Mystic Falls prepares to celebrate the traditional Illumination Night, the town is invaded by spirits of the dead. After a particularly violent encounter with an angry spirit, Damon asks Bonnie to find the reason behind the ghosts’ surprising power. Elena convinces Jeremy to use his connection to the other side to help her find a new way to reach Stefan, leading Jeremy to a terrible choice. Finally, Alaric discovers a long-hidden clue to the past.

On the first day of their senior year, Elena, Caroline, Bonnie and Matt are still reeling from recent events, while Tyler seems to be enjoying everything a little too much. Damon is annoyed by a new houseguest, and everyone is surprised by the arrival of a new student in Alaric’s history class. Matt asks Bonnie for help when he realizes he made a serious mistake. Meanwhile, Stefan continues to carry out his latest assignment from Klaus.

Despite all that has happened, Caroline is determined to see that Elena, Bonnie, Matt and Tyler all enjoy a traditional Senior Prank Night before the school year begins at Mystic Falls High School. However, when uninvited guests show up, it doesn’t take long for the evening to take a deadly turn. Damon convinces Jeremy that he can use his new connection to the other side to help find a way to defeat Klaus. Finally, Klaus deepens his hold on Stefan and uses him for increasingly violent and dangerous purposes.

Still in Chicago, Klaus uses Gloria, a witch he knew long ago, to help him track down missing information that will explain why his plan isn’t working. Gloria’s spells reveal intriguing glimpses of the truth, but she soon realizes she needs Stefan’s knowledge to complete the puzzle. When Stefan suddenly finds himself in danger, help comes from a surprising ally. Back in Mystic Falls, a frustrating new enemy pushes Damon over the brink and he lashes out in a way that will have lasting consequences. Caroline struggles with her own emotional issues, even as she tries to help Elena face her feelings. Jeremy makes a brief but disturbing breakthrough with one of his ghostly visitors, leaving him more confused than ever. Finally, Bonnie has a strange encounter that will affect everyone.

Klaus and Stefan arrive in Chicago, where Stefan is reunited with a vampire who hasn’t really moved on from her interest in him decades earlier. In a flashback to Chicago in the 1920s, Stefan comes face-to-face with a shocking chapter from his wild past. After Damon gets a tip on Stefan and Klaus’ whereabouts from an unexpected source, he and Elena follow their trail. Back in Mystic Falls, Tyler is concerned about Caroline and turns to Sheriff Forbes for help.

Klaus puts a plan in motion that will give him even more power, but even with the unwilling participation of werewolf Ray Sutton, things don’t go exactly as Klaus had planned. Damon and Alaric reluctantly go along with Elena’s new strategy to find Stefan, leading Damon into a dangerous fight with an unexpected enemy. Jeremy turns to Matt for help as he continues to try to understand what the ghosts from his past want from him. Unaware that Caroline is in need of his help, Tyler faces an emotional confrontation with his mother.

On the morning of Elena’s 18th birthday, Caroline is busy planning a party, but Elena is focused on searching for any clues that might help her discover where Stefan is. Damon is also searching for Stefan, while trying to protect Elena and keep her from doing anything that would draw Klaus’ attention. Meanwhile, Klaus and Stefan are busy trailing a werewolf named Ray Sutton. Now working at the Mystic Grill along with Matt, Jeremy is struggling to understand why he keeps seeing the ghosts of Vicki and Anna since he was brought back to life by Bonnie’s magic. Meanwhile, Alaric does his best to watch over Elena and Jeremy, while dealing with his grief over Jenna’s death. Finally, Caroline and Tyler face a new and unexpected challenge.

Mystic Falls screens “Gone with The Wind” in the town square, and Damon’s memories of Katherine in 1864 mix with the reality of present-day Elena. Stefan pays a steep price after trying to prevent a tragedy, and Sheriff Forbes makes a dangerous mistake while trying to keep everyone safe. Multiple lives hang in the balance as the consequences of the sacrifice ritual play out to a horrifying conclusion.

With the arrival of the full moon, Elena tries to prepare for whatever Klaus has planned and Tyler faces his second transformation. The terrifying events quickly spin out of control, despite an unexpected act of courage. Finally, Damon admits the truth to Stefan about a terrible new development they must face…

Damon is willing to go to extraordinary lengths to prevent Elena from being a victim of Klaus’ plan to break the curse. Damon’s actions put him at terrible odds with Stefan and the tension that started brewing between the brothers over their differing opinions of how to help save Elena’s life blows up into full-scale conflict. Tyler returns to Mystic Falls after receiving a disturbing phone call. With the full moon marking the arrival of the sacrifice ritual, Stefan and Elena spend a romantic day together — afraid it might be their last.

Stefan and Damon are furious when they discover that Elena has defied them both to make a new ally and take control of the plan to out-maneuver Klaus. Disagreement over how to protect Elena leads to growing tension between the Salvatore brothers. Meanwhile, Stefan has his hands full trying to keep a confused and frightened Jenna safe. Flashbacks to 1491 reveal Katherine’s introduction to Elijah and Klaus, along with the origin of the moonstone curse. Elena learns shocking new information about Klaus’ motives.

As the high school prepares to throw a “1960s Decade Dance,” Elena starts receiving disturbing messages from Klaus via an unusual source. Bonnie tries to reassure Jeremy that she is strong enough to help Elena, but a worried Jeremy asks Stefan for advice. Caroline talks Matt into taking her to the dance. Expecting Klaus to show up at the dance, Damon and Alaric attend as chaperones, but Klaus is playing a complicated game that keeps them on edge. Finally, Damon comes up with a new plan of action that shocks and upsets everyone.

Elena and Alaric both lash out at John when Isobel’s unexpected arrival leaves Jenna devastated. Bonnie works with Damon and Jeremy to find the spell they’ll need to harness her ancestors’ power. A heartbroken Caroline doesn’t know what to do about Matt. Stefan and Damon realize they have a new secret weapon.

Katherine’s mind games are getting on everyone’s nerves, but Damon, Stefan and Elena realize that her knowledge of Mystic Falls history will help them stay alive. Frustrated with her relationship with Matt, Caroline finds a new way to get his attention. Alaric makes a surprising confession to Jenna, and Katherine makes a different kind of confession to Damon. Stefan and Bonnie try to convince Jonas and Luka that they should all be working together, but Jonas’ lack of trust leads to a violent and fiery confrontation.

Stefan tells Elena about a dark time in his history and the surprising person whose influence changed everything. After getting the truth out of Luka, Jonas makes his feelings clear to Bonnie and Jeremy. Trying to catch Elijah off-guard, Damon arranges a dinner party for him with Jenna, Alaric and Andie, but last-minute information throws Damon’s plan into chaos.

Stefan and Elena get away for what they hope will be a romantic weekend at the Gilbert family lake house, not realizing that they’ve been followed. Jenna starts to worry that Alaric isn’t being honest with her. Jules explains the importance of the sun and moon curse to Tyler, but leaves out an important detail. Damon attends a tea at the Historical Society in order to talk to Elijah, but Elijah isn’t giving up any secrets. With help from Caroline and Jeremy, Bonnie uses deceptive measures to get shocking new information out of Luka. Finally, Tyler offers Matt some relationship advice.

Johnathan Gilbert’s return to Mystic Falls comes as an unhappy surprise to Elena, Jenna and Damon. Caroline lets Stefan know about her conversation with Tyler, and Stefan does his best to reach out to a confused and conflicted Tyler. Jeremy comforts Bonnie after her disturbing conversation with Jonas… When Jules takes a hostage, the situation quickly escalates into a violent confrontation.

Stefan has his own ideas about Elena’s new plan for the future. While Damon tries to get the truth out of Jules, he asks Elena to keep an eye on Rose, a situation that turns unexpectedly dangerous. Caroline and Matt try to be honest about their feelings for one another, and Tyler’s reaction to Caroline’s generosity comes as a surprise to her… Damon struggles to hide his true feelings when a life-and-death crisis hits him harder than he expected.

As the full moon approaches, Caroline helps Tyler prepare for the transformation he is powerless to stop. While Stefan and Katherine play mind games on one another, Damon and Alaric are suspicious when a stranger named Jules shows up in Mystic Falls, searching for her missing friend, Mason. Elena is frustrated at the lengths Jeremy and her friends have gone to in order to keep her safe. Bonnie and Luca work together on a spell, while still keeping secrets from one another. Finally, Elijah makes an unexpected appearance with an offer that could change everything.

Elena decides to take matters into her own hands and offers a tempting incentive to Rose for her help. When things take an unexpected turn, however, Rose calls on Damon to deal with the plan Elena has set in motion. Jeremy’s reckless attempt to help Bonnie retrieve the moonstone lands him in a life-threatening position and forces Stefan to put himself in danger. Bonnie and Luka form a closer connection. Tyler shows Caroline the Lockwood cellar, where she makes a discovery that leaves them both terrified.

Elena puts herself in a dangerous position as she searches for the truth about Katherine’s past and what her own future may hold. Knowing that Stefan would never agree to her plan, Elena swears Caroline to secrecy. Damon uses a new-found confidant to help him try to discover the real purpose and power of the moonstone. Jeremy and Bonnie meet Luka, a new student with a surprising family history.

An Ancient Presence In Mystic Falls, Stefan and Damon come to Elena’s assistance and, in the process, learn surprising new information about people, vampires and events in the distant past. Jeremy helps Bonnie after she casts a difficult and exhausting spell, and Caroline does what she can to make things easier for Tyler. Finally, Stefan and Damon reach a new understanding.

Stefan and Damon decide on a new plan to deal with Katherine at the Lockwood’s masquerade ball. Katherine calls on an old friend, Lucy, to attend the ball with her. Bonnie, Jeremy and Alaric all do what they can to help Stefan and Damon, but Katherine has a surprise planned that none of them could foresee. Things take an ugly turn when Matt and Tyler start doing shots with their friends.

Despite Elena’s efforts to keep Jeremy safe, he offers to help Damon and Alaric deal with Katherine… Sheriff Forbes and Caroline share a few rare moments of quality mother/daughter time. Bonnie accidentally discovers new information about Mason and shares it with Stefan, leading Damon to take matters into his own hands.

Tyler learns more about the Lockwood family curse from Mason. Stefan and Damon argue over how to handle Mason. Elena tries to keep Jeremy from becoming more involved with the Lockwood mystery, but Jeremy makes an effort to hang out with Tyler. Mason gives Sheriff Lockwood some startling information, leading to a night of violence, confession and heartbreak.

Stefan takes drastic measures to find out the real reason Katherine has returned to Mystic Falls, and is shocked when she reveals new secrets about what really happened in 1864. Damon tries a new tactic to resolve his issues with Mason,…. but it proves costly. Tyler pushes Mason to tell him the truth about the Lockwoods. Finally, when Katherine delivers an ultimatum, Stefan and Elena are left with very few options.

Elena, Damon and Alaric take a road trip to Duke University and search through Isobel’s research on folklore and paranormal phenomena to see if they can uncover any clues to the mystery surrounding the Lockwood family. Isobel’s former student, Vanessa offers to guide them through the research and ends up getting quite an education herself. Stefan comes face to face with a terrifying new danger in the woods, and Tyler makes a shocking discovery about Mason…..

When a confused and desperate Caroline leaves the hospital and joins her friends at the Mystic Falls Carnival, Damon wants to take immediate action, but Stefan and Elena come to Caroline’s defense. Matt is completely mystified by Caroline’s behavior, but still tries to tell her about his feelings for her.. Damon has suspicions about Tyler’s Uncle Mason and uses Tyler’s volatile personality in an attempt to get Mason to reveal his secret. Upset with everything going on around her, Bonnie takes her anger out on Damon.

The second season begins with Elena discovering her uncle John’s bloody body and learning Jeremy’s fate, and Damon realizing that Katherine has returned. Meanwhile, Caroline is taken to the hospital following a car accident, and Tyler’s mysterious uncle Mason arrives in town.

Founder’s Day has finally arrived, and everyone is busy with last-minute preparations for floats and fireworks. Stefan is uncomfortable with Damon’s new attitude toward Elena, but Elena is more concerned about repairing her relationship with Jeremy. Jeremy is worried about Anna, but not sure he’s on board with her latest plan for the future. While Caroline is enjoying her day as Queen of the celebration, she also tries to help Matt and Tyler get their friendship back on track. Finally, although Damon and Alaric do their best to stop him, Johnathan Gilbert sets a plan in motion that brings Founder’s Day to an end amid chaos, destruction and death.