Matt and Caroline are surprised by the sudden reappearance of Matt’s mother Kelly. Stefan and Elena are worried about Damon’s new attitude. Damon is asked by Sheriff Forbes to take part in a fund-raising bachelor auction. Alaric discovers shocking secrets from his own past. With help from Jenna and Stefan, Elena is determined to find out everything she can about her birth mother, but the truth may be more than she can handle.

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 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.

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 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.

Alaric finds an unexpected ally to guide him on his dangerous new path, while Damon and Meredith try to figure out what their next move should be. At the school’s 1920s Decade Dance, Bonnie asks Jamie to go with her and, at Caroline’s suggestion, Elena asks Stefan to be her date. Caroline is pleasantly surprised when Tyle shows up at the dance determined to sweep her off her feet, but Klaus does his best to come between them. The dance takes a deadly turn when Damon and Stefan realize they need the help of Matt, Jeremy and especially Bonnie to undo a spell that could prove devastating for everyone.

Damon goes with Elena and Bonnie to visit Whitmore College, where Professor Shane is taking over the Occult Studies classes formerly taught by Bonnie’s grandmother. At a fraternity costume party, Damon takes advantage of the wild scene to give Elena a lesson in choosing a victim. Rebekah’s attempt to buy Matt’s forgiveness falls flat, but she is intrigued by unexpected news from Klaus. When Stefan questions Klaus about Connor’s motives, Klaus reveals a long-ago encounter with a powerful group of vampire hunters, but it’s Rebekah who delivers the information that stuns Stefan.

A fellow Whitmore student named Jesse gives Elena some intriguing information about Professor Wes Maxfield. Damon asks for help finding Stefan.

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.

As Caroline and Elena prepare to host Friendsgiving at the dorm, they receive some hopeful news from Alaric and Stefan, who have traveled to Portland to gather some information regarding the Gemini Coven. Tyler is determined to help Liv after she and Luke reveal some disturbing information about their witch lineage and the impending plans their coven has for them. Meanwhile, dinner takes a drastic turn when Jo, who has revealed some painful details about her past, finds herself fighting for her life, leaving Alaric scrambling to help from a distance. Finally, Kai makes a dangerous discovery that brings him one step closer to his release.

With the help of Bonnie and Kai, Damon and Elena set forth a plan to rescue Damon's mother Lily, who is trapped in the 1903 prison world. Meanwhile, when Caroline's plan for Stefan backfires, she is left to pick up the pieces. Elsewhere, back at Whitmore College, Enzo and Alaric's attempt to reel Caroline back in doesn't quite go as planned when they realize they're outmaneuvered. Lastly, an unexpected gift from Bonnie leaves Damon shaken to his core.