Season 5 begins with Elena and Caroline moving into a dorm at nearby Whitmore College and getting an unexpected third roommate. Meanwhile, Katherine pleads with Damon to help her now that she is human and vulnerable to her enemies; and Silas makes a terrifying appearance at an end-of-summer party in the town square. (TV Guide)

Damon asks sheriff Forbes for help to find Stefan; Elena and Caroline try to find out who is covering up a campus murder; Matt and Jeremy attempt to protect Katherine from Silas; Nadia uses violence to make a point about her own agenda. (TV Guide)

Elena and Katherine both dream that Stefan is in danger and convince Damon to help them find him. But their plans are thwarted by a mysterious woman who seems to know everything about Stefan's past and Damon's disturbing future. (TV Guide)

Elena and Damon attempt to help Stefan through a confusing time; Matt tries to figure out the reason behind his mysterious blackouts; Caroline makes an effort to get to know Jesse better; Jeremy makes a startling confession; Dr. Maxfield puts in motion a plan that threatens to change everything. (TV Guide)

Elena meets a sad and secretive student on campus. Later, Elena and Damon attend the Whitmore Historical Ball dressed as Anne Boleyn and Henry VIII. While there, Elena receives a disturbing message from Dr. Maxfield. Meanwhile, Nadia reveals her surprising history to Katherine; and Silas demands that Damon commit an unthinkable act. (TV Guide)

Silas announces his new goal to Damon and Elena; Tessa tells Stefan about her next move; Katherine discovers an unexpected consequence of being human and realizes she needs a new place to stay; Bonnie is touched by Jeremy's determination to stand by her; Damon is stunned when he learns the secret to Tessa's plan. (TV Guide)

While Elena and Damon try to explain Amara's situation to Stefan, Dr. Wes gives Katherine some deeply disturbing news. Silas fails to keep a promise, causing Damon to turn to Tessa for help with his new plan, and Stefan makes a heartbreaking confession to Damon and Elena. (The CW)

At Whitmore College, Elena and Caroline decide it's time to throw a big party, but their plans are interrupted when Jesse suddenly needs Caroline's help. Finally, Damon makes a terrifying discovery about a secret society. (The CW)

Caroline offers Stefan an unusual form of therapy. Meanwhile, Damon tells Elena about a terrible ordeal in his past that he has kept secret for decades, and she shares with him some disturbing information she recently learned about her family. (TV Guide)

Damon is forced to deal with a part of his past he thought was gone forever when Dr. Wes unleashes a secret weapon to stop him from rescuing Elena. Meanwhile, Elena learns about the dark history of Whitmore College; and Katherine turns to Matt for help. (TV Guide)

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. (TV Guide)

Enzo brings Damon a gruesome present and insists that they bond by committing an act of revenge; Matt impulsively decides to throw a party; Caroline makes a stunning confession to Elena; Aaron tries to make amends for his family's past misdeeds; Elena faces a life-threatening situation with only minutes to figure out how to save herself. (TV Guide)

Caroline convinces Elena and Bonnie to attend Whitmore College's Bitter Ball for broken-hearted students; and Bonnie meets a fellow student who appears to be dabbling in witchcraft. Meanwhile, Tyler worries about Matt's relationship with Nadia; and Damon and Enzo resort to violence to convince Bonnie and Jeremy to help them get revenge, but their plan takes a horrifying turn. (TV Guide)

Damon's behavior escalates from destructive to deadly. Stefan begins to regret their last conversation and tries to track Damon down and intervene. Meanwhile, Dr. Wes enlists the Travelers to set a trap that will test Damon's friendship with Enzo; and a talk between Caroline and Stefan leads to a horrifying realization. (TV Guide)

Nadia recalls her centuries-long search for her mother; Stefan, Caroline and Matt come up with a desperate plan to save Elena's life; Damon baits Tyler into an ugly confrontation and seeks revenge against Dr. Wes; Bonnie learns a terrifying secret that threatens the lives of all her friends. (TV Guide)

Damon tries to find the right way to make a disturbing confession to Elena; Caroline discovers a scary secret in Dr. Wes' files; Enzo claims to have a solution everyone is searching for; Sloan reveals new information on the importance of doppelgangers. (TV Guide)

Damon tells Elena some upsetting news about Jeremy's personal life; Enzo opens up to Caroline about his past; Bonnie experiences an unsettling encounter with Luke; the mysterious leader of the Travelers appears after some terrifying events at a camp. (TV Guide)

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 learns that Jeremy is working with Liv; Matt has a terrifying encounter with inhabitants of the Other Side. (TV Guide)

Enzo, through flashbacks to election night in 1960, learns what happened to his long-lost love; Elena obsesses over the state of her relationship with Damon; Markos enlists Sloan's help in a ritual designed to break an ancient curse against the Travelers. (TV Guide)

Damon takes Stefan and Elena to a cabin to keep them safe, and then he devises a parlor game to get them to reveal a secret they've been hiding. Meanwhile, Bonnie keeps Jeremy in the dark regarding the truth about the Other Side. (TV Guide)

Stefan and Elena become stranded in a remote location, after escaping from Markos, and he gets philosophical about her relationship with Damon. Meanwhile, Damon sets a trap for Markos; Bonnie admits that she's been keeping the truth about the Other Side from everyone; and Caroline witnesses an unthinkable act of violence by one of the Travelers. (TV Guide)

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. (TV Guide)