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- Season 5 overviewOct 3, 2013-May 15, 201422 episodesSeason 5 episodes1. I Know What You Did Last Summer Oct 3, 2013
- Elena moves to college with Caroline; a student named Megan shows up in Bonnie's place at the dorm.
- 2. True Lies Oct 10, 2013
- Damon tries to find Stefan without telling Elena that he is missing.
- 3. Original Sin Oct 17, 2013
- Katherine and Elena have the same dream about Stefan being in danger.
- 4. For Whom the Bell Tolls Oct 24, 2013
- Elena and Damon try to help Stefan through a confusing time; Jeremy makes a confession.
- 5. Monster's Ball Oct 31, 2013
- Damon and Elena attend the Whitmore historical ball; Caroline's happiness turns to heartbreak.
- 6. Handle With Care Nov 7, 2013
- Damon and Elena are skeptical of Silas's new goal; Tessa realizes she was outsmarted by Silas.
- 7. Death and the Maiden Nov 14, 2013
- Damon and Elena attempt to explain Amara's situation to Stefan; Katherine receives disturbing news.
- 8. Dead Man on Campus Nov 21, 2013
- Caroline and Elena decide to throw a big party; Damon makes a discovery about a secret society.
- 9. The Cell Dec 5, 2013
- Stefan tries to mask his pain as he offers Katherine support; Elena asks Aaron for help.
- 10. Fifty Shades of Grayson Dec 12, 2013
- Damon asks Stefan for help finding Elena; Dr. Wes unleashes his secret weapon.
- 11. 500 Years of Solitude Jan 23, 2014
- Katherine remembers the night she gave birth to a baby girl who was immediately taken away.
- 12. The Devil Inside Jan 30, 2014
- Damon receives a grisly gift from Enzo; Matt throws an impromptu party.
- 13. Total Eclipse of the Heart Feb 6, 2014
- Caroline talks Bonnie and Elena into attending a dance for broken-hearted students.
- 14. No Exit Feb 27, 2014
- Stefan decides to track down Damon, whose behavior has escalated from destructive to deadly.
- 15. Gone Girl Mar 6, 2014
- Nadia remembers the centuries she spent searching for her mother; a desperate plan to save Elena.
- 16. While You Were Sleeping Mar 20, 2014
- Damon tries to figure out how to make a disturbing confession; Caroline uncovers a secret.
- 17. Rescue Me Mar 27, 2014
- Enzo and Caroline go on a trip and find another doppleganger; Bonnie has an encounter with Luke.
- 18. Resident Evil Apr 17, 2014
- Elena and Stefan start having dreams about an alternate version of their lives.
- 19. Man on Fire Apr 24, 2014
- Stefan tries to distract Elena from her relationship problems; Enzo reveals what happened to Maggie.
- 20. What Lies Beneath May 1, 2014
- When Stefan and Elena are put in imminent danger, Damon suggests they hide in a remote cabin.
- 21. Promised Land May 8, 2014
- Stefan and Elena are stranded in a remote location; Luke and Liv form a dangerous new strategy.
- 22. Home May 15, 2014
- Damon focuses on holding himself together after an unexpected tragedy.