The present-day murders in Mystic Falls remind Damon of a similar crime spree a century earlier. Flashing back to 1912, Damon recalls a beautiful vampire.

Stefan still struggles desperately to get his blood-lust back under control. Damon keeps an eye on him, but has other priorities. Damon's former teacher Sage returns as his lover, in a secret pact against Rebekah, whom he seduces to keep an eye on her quest for the original white oak's sole known shoot. The old vampires are actually in league and torch the bridge made from its wood, fearing the weapon that could be made from it, but Damon stayed a step ahead. Dr. Fell tries to treat Alaric medically while Bonnie attempts to undo the curse which caused his hereditary madness, but they aren't careful enough, so Damon must intervene. Jeremy calls home from Denver, reporting that he only suffers from melancholy, but is doing well at school.

Stefan's emotional turmoil leads him to a dangerous confrontation with Klaus and, later to a heartbreaking moment with Elena. Claire Holt and Casper Zafer guest star