After reading the journal left by one of the Gilbert ancestors, Jeremy is inspired to return to his hobby of sketching fantasy creatures, a talent he had abandoned when his parents died. Much to the surprise of their friends, Matt and Caroline continue to hang out together. When Sheriff Forbes tells Damon there has been another attack, he offers to track down the killer and learns a startling piece of information about the town's founding families. Alaric steps in to help during an awkward scene with Jeremy, Tyler and Mayor Lockwood. Stefan and Elena come to a new understanding, but everything changes when Elena accidentally makes a devastating discovery

As Stefan and Damon try to figure out the identity of the new vampire in town, Stefan gives Elena jewelry filled with Vervain to protect her family and friends. Hurting for money, Matt takes a job at the Mystic Grill, where former high school football-star Ben, works as a bartender. Ben comes to Bonnie's aid when he notices Damon is bothering her. Damon and Stefan accompany Elena to a school dance with a 1950s' theme, where Alaric introduces himself to Damon.