While Stefan struggles to control his new situation, Elena and Jeremy are surprised by a visit from their uncle, John Gilbert. Alaric has an awkward talk with Elena about Isobel. At a Founder’s Day event, Stefan displays a rare party attitude and Damon’s attempt to find out why Uncle John has returned to town takes an ugly turn. An incident at the party causes trouble between Matt and Tyler... and the relationship between Matt and his mother, Kelly, reaches a new low. Meanwhile, Elena’s effort to comfort Jeremy falls short and he decides to take matters into his own hands.

At the Founder’s Day Gala, Elena and Caroline compete for the title of “Miss Mystic Falls” against other girls from town, including Tina Fell and Amber Bradley. Elena is happy to have Bonnie back in town, but Bonnie still has issues to work through. John Gilbert attempts to intimidate Damon, but his plan doesn’t have the desired effect. Damon discovers that Stefan is hiding a dangerous secret that could impact everyone in town.

While Stefan struggles to come to terms with his past, both he and Damon reveal parts of their history to Elena, until she finally learns the truth about how they became vampires. Pearl has an ugly confrontation with Johnathan Gilbert. Damon and Alaric try to find a mysterious invention before Johnathan does. The friendship and flirtation between Jeremy and Anna continues to grow.

Isobel returns to town and stuns Alaric with her attitude and her demands that he arrange a meeting with Elena. When mother and daughter finally meet, Isobel refuses to answer most of Elena’s questions, but reveals that she will stop at nothing to find the mysterious invention Johnathan Gilbert has been searching for. Isobel’s dangerous actions lead Stefan, Damon and Bonnie to step in and help Elena deal with the situation.

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.

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.

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.

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 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.

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.

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.

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...

Katherine recalls the traumatic night in 1490 when she gave birth to a daughter who was immediately taken from her. Meanwhile, Nadia creates a frightening plan to protect her mother; and Caroline indulges in some scandalous behavior.

With the fate of Mystic Falls at stake, Stefan and Damon must fight their greatest enemy for one last battle.