An old friend (Arielle Kebbel) visits Stefan on his birthday and she gives Elena some insight into dating him. Meanwhile, Caroline attempts to get Damon's medallion back from Bonnie, and Damon offers to help Sheriff Forbes, which leads to tragedy.

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