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Elena Gilbert and her brother Jeremy come to terms with the death of their parents. Elena is popular amongst her peers and the perfect straight A student, but has difficulties hiding her grief from the world. Meanwhile, Jeremy treads on a dangerous path of using drugs to ease his pain. The arrival of new student Stefan Salvatore, however, makes Elena think about romantic possibilities.
Mystic Falls begins the preparations to celebrate the passing of a comet. Vicki recuperates in the hospital from her injuries. Stefan uses his abilities to erase Vicki's attacker from her memory, but is interrupted by Matt. Mr. Tanner warns Aunt Jenna about Jeremy. Elena and Damon meet for the first time at the Salvatore house and his revelation on Stefan's past brings Elena closer to the truth. Damon finds his next victim in Caroline.
Bonnie warns Elena about Stefan. Tyler attempts to humiliate Stefan but it backfires as Stefan catches and passes the ball back, winning everyone over. Damon and Caroline gate crash any plans Elena had for Stefan and Bonnie to get along.
Elena and Stefan go to the town's annual Founder's Party. Vicki wants Tyler to take her to the party. Damon tells Elena about the history of the Salvatores. Stefan tries to cut Damon out of his life.
Elena and Jenna have a problem with Jeremy's relationship with Vicki. Stefan comes clean about his past to Elena. At a fund-raiser, Bonnie is taken aback by how advanced her powers are, and turns to her grandmother for guidance. Elena uncovers some news about the Salvatore family.
Elena seeks answers from Stefan about all the bad things happening in Mystic Falls. Stefan reveals how the rivalry with his brother began through a series of flashbacks. Damon controls Vicki's future. Meanwhile, Sheriff Forbes and Mayor Lockwood try to protect their town.
Stefan tries to save Vicki from herself. Damon tries to take his necklace back from Bonnie, he is shocked by Bonnie's powers. Bonnie discovers more about her family's history. Matt takes Vicki to a haunted house.
On his birthday, Stefan is surprised by a visit from Lexi, one of his oldest friends. Elena keeps Stefan at arms length, but Lexi gives her some unsolicited relationship advice. At Damon's command, Caroline tries to get his medallion back from Bonnie. Damon makes a kill that angers Stefan. FInally Bonnie reveals the truth to Elena that she is a witch.
Stefan learns the reason Damon returned to Mystic Falls - Jeremy gets a break from the mysterious new history teacher, Alaric Saltzman and introduces Alaric to Jenna. Bonnie is having terrifying dreams about one of her ancestors. Despite Elena's efforts to smooth things over, Bonnie and Caroline continue to argue over the medallion. When the girls hold a séance to help them decide what to do, the results are stranger than any of them expected. Matt comes to Caroline's aid when she needs a friend. Damon finally reveals to Stefan the stunning reason he has returned to Mystic Falls.
Stefan and Damon find a common enemy and someone they deem to be a threat. Meanwhile, Elena confesses her love for Stefan and persuades him to stay in Mystic Falls, but she also makes a devastating discovery that adversely affects her relationship with him. Jeremy takes up drawing fantasy creatures again.
Damon travels to Georgia, where he goes to visit, Bree a former lover to help him open the tomb. To make things even more interesting Damon has to face someone from the past seeking vengence. Stefan tries to help Bonnie overcome her fears and accept her powers. Jeremy meets a girl named Anna who has her own theories on the mysteries behind Mystic Falls.
Damon, Elena and Stefan attend the school dance with a 1950s' theme, where Alaric introduces himself to Damon. Stefan and Damon try to figure out the identity of the new vampire in town, and Stefan gives Elena jewelry filled with vervain to protect her family and friends. To make ends meet, Matt takes a job at the Mystic Grill. Ben comes to help Bonnie when he notices Damon is bothering her.
In flashbacks, Stefan and Damon recall the long-ago actions taken by townspeople including their father, Guiseppe Salvatore, and Pearl, leading to the devastating events that caused the rift in their relationship. In the present, Bonnie's date with Ben takes a frightening turn. Elena helps Stefan as he and Damon race to find the missing journal that belonged to Elena's ancestor. Stefan learns the reason behind Alaric's interest in both the journal and the town's history. Damon discovers that an old acquaintance has returned to town with an agenda he understands.
Stefan helps Elena and Bonnie out of a dangerous situation. Jeremy asks Anna to a party in the woods, unaware that she has her own reasons for wanting to meet him there. When Stefan, Damon and Elena work with Bonnie and Grams to open the tomb, everyone is shocked by what they discover.
Matt and Caroline are surprised when Matt's long-lost mother returns to Mystic Falls. Elena and Stefan are concerned about Damon's new positive attitude, and Alaric makes some surprising discoveries about his past life. Meanwhile, Stefan and Jenna help Elena search for information about her birth mother.
Anna visits Damon and brings along an unexpected guest. Elena and Stefan endure an awkward double date with Caroline and Matt, but Stefan and Matt start to bond after realizing they share some common ground. Jenna reunites with her old friend Kelly, and Jeremy and Anna's relationship moves in a new direction.
Stefan and Damon make a new enemy, which puts Stefan in a dangerous situation. Damon and Elena try to enlist Alaric's assistance in helping Stefan. Matt hopes that his mother may finally be back for good. Caroline's car breaks down during a storm, leading her to make a terrible discovery that shocks everyone in Mystic Falls.
Stefan struggles to maintain control of his new circumstances, and Elena and Jeremy's uncle, John Gilbert, unexpectedly shows up in Mystic Falls. Alaric and Elena have an awkward conversation about Isobel. Stefan exhibits some unusual behavior at the Founder's Day event, and things turn ugly when Damon tries to find out why John Gilbert has returned. Matt and Tyler find themselves in conflict after an incident at the party, and the relationship between Matt and his mom reaches a new low point. Meanwhile, Elena is unable to comfort Jeremy, causing him to take action.
At the Founder's Day Gala, Elena and Caroline compete in the "Miss Mystic Fall" contest. Elena is very happy to have Bonnie back but Bonnie still has some issues to work. Meanwhile, John Gilbert tries unsuccessfully to intimidate Damon, and Damon discovers that Stefan is hiding a very dangerous secret.
As Stefan tries to come to terms with his past, he and Damon reveal pieces of their history to Elena, including the truth about how they were turned into vampires. Pearl and Jonathan Gilbert have an an ugly confrontation. Damon and Alaric attempt to track down a mysterious invention before Johnathan can find it. Jeremy and Anna's relationship continues to grow.
Isobel returns to town and surprises Alaric with a new attitude and demands that he arrange for her to meet Elena. When the two finally meet, Isobel refuses to answer most of Elena's questions, but instead reveals that she, too, is looking for the mysterious invention that John Gilbert has been seeking.
It's Founder's Day, and everyone is preparing for floats and fireworks. Though Damon and Alaric try to stop Johnathan Gilbert, he sets his plan in motion, leading to a chaotic, destructive, and deadly end to the Founder's Day celebration.
Elena returns home and is horrified to learn what has happened to Jeremy and Uncle John. Bonnie, Matt, and Damon wait at the hospital with Sheriff Forbes, who is anxious to hear whether Caroline will survive the car accident. Elena and Damon share a confusing conversation about the evening's events, and Damon realizes that Katherine has returned. He and Stefan set out to learn why Katherine came back and whether she poses a threat to Mystic Falls. Tyler's uncle, Mason, arrives to console his family members, who are still grieving after the mayor's death.
Caroline, feeling confused and desperate, joins her friends at the Mystic Falls Carnival after being released from the hospital. Damon wants to take immediate action, but Stefan and Elena offer Caroline their support. Matt tries to tell Caroline how he feels about her despite being confused about her behavior. Damon starts to suspect Mason Lockwood and tries to use Tyler's short temper to get Mason to reveal his secret. Bonnie takes her frustrations out on Damon as she becomes frustrated with everything going on around her.
Elena, Damon, and Alaric travel to Duke University to study Isobel's research on folklore and paranormal phenomena, hoping to find some clues to the mystery surrounding the Lockwoods. Vanessa, a former student of Isobel's, helps them sort through the research and ends up learning more than she had anticipated. Stefan encounters a terrifying new danger in the woods, and Tyler uncovers a shocking discovery about his uncle Mason.
Stefan takes more dramatic actions as he tries to discover the truth behind why Katherine has returned to Mystic Falls, and he is stunned when Katherine reveals some new information about the events that unfolded in 1864. Damon tries using a new method to resolve his issues with Mason, but his decision has serious consequences. Tyler pressures Mason to tell him the truth about the Lockwood family. Stefan and Elena are faced with limited options when Katherine gives them an ultimatum.
While Stefan and Damon argue over how to handle the Lockwoods, Tyler learns more about his Uncle Mason and the family curse. Despite Elena's wishes, Jeremy gets closer to the Lockwood mystery by hanging out with Tyler. Sheriff Forbes receives some shocking information from Mason, leading to a chaotic night.
Jeremy offers to help Alaric and Damon deal with Katherine, despite Elena's concerns about Jeremy's safety. Caroline and her mother share some rare quality time together. When Bonnie learns some new information about Mason, she decides to share it with Stefan, which leads to Damon taking action on his own.
Damon and Stefan devise a new plan to deal with Katherine at the Lockwood's masquerade ball. Katherine asks her friend, Lucy, to join her at the ball. Bonnie, Alaric, and Jeremy do their best to help Stefan and Damon with their plan, but Katherine has a surprise that none of them expected. The evening takes a bad turn when Tyler and Matt start doing shots with their friends.
Jeremy teams up with Bonnie after she casts a difficult spell. Stefan and Damon both come to Elena's assistance, and in the process, learn some information about vampires, people and events in the distant past. The brothers also come to reach a new understanding. Meanwhile, Caroline tries to make things easier for Tyler.
Elena is put in peril when as she searches for information about Katherine's past. Knowing that Stefan would disagree with her plan, Elena swears Caroline to secrecy. Meanwhile Bonnie and Jeremy meet a new student, Luka, with an unusual family history and Damon uses a new-found confident to discover the purpose of the moonstone.
Elena comes up with her own plan to deal with her situation and offers Rose a tempting incentive for her help. When plans change unexpectedly, Rose asks Damon to help with Elena's plan. Tyler shows Caroline the Lockwood's cellar where she makes a terrifying discovery. Jeremy and Bonnie attempt to retrieve the moonstone, but Stefan ends up in danger when things don't go as planned. Bonnie and Luka also become closer.
With a full moon approaching, Caroline helps Tyler prepare for his inevitable transformation. Stefan and Katherine play mind games on each other, and Damon and Alaric become suspicious when a mysterious visitor named Jules shows up in Mystic Falls, looking for her missing friend, Mason. Elena is frustrated at Jeremy and her friends' excessive efforts to protect her. Bonnie and Luca team up to work on a spell, though both continue to keep secrets from each other. Finally, Elijah makes an unexpected appearance with an offer that could change everything.
Elena has a new plan for the future, but Stefan has his own thoughts about how she should handle the situation. Damon tries to get the truth out of Jules and asks Elena to watch Rose, but things quickly become dangerous. Matt and Caroline try to be honest about how they feel about each other, and Caroline is surprised to see how Tyler reacts to her generosity. Damon finds it difficult to hide his true feelings when a life-and-death situation impacts him more than he expected.
Elena, Damon, and Jenna are surprised when Johnathan Gilbert returns to Mystic Falls. Caroline tells Stefan about her conversation with Tyler, and Stefan tries to help a confused Tyler. Jeremy consoles Bonnie after her upsetting conversation with Jonas. A violent situation breaks out after Jules takes a hostage.
Stefan and Elena make plans for a romantic weekend at the Gilbert's lake house, not realizing that someone has followed them. Jenna starts to worry that Alaric isn't being completely honest with her. Jules explains the significance of the sun and moon curse to Tyler, but leaves out an important detail. Damon attends a tea party at the Historical Society to get a chance to talk to Elijah, but Elijah refuses to divulge any secrets. With help from Caroline and Jeremy, Bonnie deceives Luka into giving up some surprising new information. Tyler offers Matt some relationship advice.
Stefan tells Elena about a dark time from his past and the unexpected person who changed everything for him. Jonas gets the truth out of Luka and makes his feelings clear to Bonnie and Jeremy. Damon schedules a dinner party with Alaric, Jenna, and Andie in attempt to catch Elijah off-guard, but some last-minute information disrupts Damon's plan.
Even though Elena, Damon, and Stefan are tired of Katherine's constant mind games, they realize that Katherine's knowledge of Mystic Falls history will help them survive. Caroline finds a new way to get Matt's attention after feeling frustrated with their relationship. Alaric reveals some shocking information 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 intense confrontation.
Elena and Alaric are upset with John after Isobel's unexpected arrival devastates Jenna. Damon, Jeremy, and Bonnie search for the spell they'll need to harness the power of Bonnie's ancestors. Caroline, heartbroken, doesn't know how to handle the situation with Matt. Damon and Stefan realize they have a new secret weapon.
The high school gets ready for a 1960s-themed dance and beings receiving alarming messages from Klaus via an unusual source. Bonnie tries to convince Jeremy that she has enough strength to help Elena, but Jeremy, concerned, goes to Stefan for advice. Caroline convinces talks Matt to take her to the dance. Damon and Alaric attend the dance as chaperons, expecting Klaus to show up, but Klaus is playing a complicated game that keeps them guessing. Eventually, Damon comes up with a new plan that surprises and upsets everyone.
Damon and Stefan are furious when they learn that Elena has gone against their wishes and formed a new alliance in attempt to out-maneuver Klaus. Tension between Damon and Stefan grows as they disagree over how best to protect Elena. Meanwhile, Stefan has his hands full as he tries to protect a confused and frightened Jenna. Flashbacks to 1491 reveal Katherine's initial meeting of Elijah and Klaus, along with the origin of the moonstone curse. Elena discovers some surprising new information about Klaus' intentions.
Damon is willing to take extreme measures to prevent Klaus from harming Elena. His actions pit Damon and Stefan against one another, and the tension that started brewing between the two over their differing opinions of how to protest Elena turns into a full-scale conflict. Tyler receives a concerning phone call and returns to Mystic Falls. With the full moon marking the arrival of the sacrifice ritual, Stefan and Elena spend a romantic day together, worried that it might be their last.
With the arrival of the full moon, Elena attempts to get ready for whatever Klaus has in store for her, and Tyler faces his second transformation. The dangerous events quickly escalate out of control, despite an unexpected act of courage. Damon reveals the truth to Stefan about a terrible new development they now face.
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.
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.
Klaus attempts to execute a plan that will give him even more power, but things don't go as he planned. Alaric and Damon hesitantly go along with Elena's search for Stefan, but her plan may end up putting Damon in danger. Jeremy asks for Matt's help to find out what his ghosts want from him, and Caroline needs Tyler's help.
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 contacts Chicago witch Gloria to help him find the reasons why his plan isn't working as he expected. Gloria, though able to see glimpses of the puzzle, needs Stefan's help to piece it all together. Damon is pushed to his limits by a new enemy in Mystic Falls with far reaching effects. Even while helping Elena confront her feelings, Caroline tries to cope with her own emotions. Jeremy is left extremely confused after a dramatic and important discovery with one of his ghosts. But it's an unexpected meeting involving Bonnie that will touch everyone's lives.
Elena, Bonnie, Matt and Tyler decide to oblige Caroline when she urges them to celebrate Senior Prank Night, but uninvited guests make for a deadly evening. Damon convinces Jeremy that his connection to the other side may be the way to defeat Klaus. Klaus uses Stefan for more dangerous and brutal intentions.
On the first day of their senior year, Elena, Matt, Bonnie, and Caroline are still dealing with the recent events, yet Tyler seems to be enjoying his new reality a little too much. Damon is frustrated by the new guest in his house, and everyone is caught off guard when a new student joins Alaric's history class. Matt looks to Bonnie for help after realizing that he made a big mistake. Meanwhile, Stefan continues to follow Klaus's orders and carry out his latest assignment.
As the town prepares to celebrate the traditional Illumination Night, spirits of the dead invade Mystic Falls. After a brutal attack by an angry spirit, Damon asks Bonnie to determine the source of the ghosts' surprising power. Elena talks Jeremy into using his connection to the other side to help her explore new ways to reach Stefan, but Jeremy makes a terrible decision. Meanwhile, Alaric discovers a long-hidden clue that gives him new insight about the past.
Elena and Bonnie help Alaric in his effort to decipher the meaning behind his recent discovery. Elena and Rebekah find themselves in a mean-girl power struggle until Rebekah finally reveals some of her family's ancient secrets and her violent past with Klaus and Elijah. Still trying to make a breakthrough with Stefan, Damon tries a reckless new approach, and they're both surprised by an unlikely ally.
Elena is uneasy and confused after Rebekah tells her why the night of the Homecoming dance is so significant. Tyler's actions during the evening leave Matt and Caroline shaken. Things turn bizarre when Klaus decides to activate his latest plan and, while trying to outsmart him, Damon forms a risky liaison which gives rise to a horrifying unforeseen development.
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.
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.