Anna Enger Ritch

Stefan has his own ideas about Elena’s new plan for the future. While Damon tries to get the truth out of Jules, he asks Elena to keep an eye on Rose, a situation that turns unexpectedly dangerous. Caroline and Matt try to be honest about their feelings for one another, and Tyler’s reaction to Caroline’s generosity comes as a surprise to her... Damon struggles to hide his true feelings when a life-and-death crisis hits him harder than he expected.

Caroline is determined to see that Elena, Bonnie, Matt and Tyler all enjoy a traditional Senior Prank Night before the school year begins … but the evening takes a deadly turn.

As the high school prepares to throw a "1960s Decade Dance," Elena starts receiving disturbing messages from Klaus via an unusual source. Bonnie tries to reassure Jeremy that she is strong enough to help Elena, but a worried Jeremy asks Stefan for advice. Caroline talks Matt into taking her to the dance. Expecting Klaus to show up at the dance, Damon and Alaric attend as chaperones, but Klaus is playing a complicated game that keeps them on edge. Finally, Damon comes up with a new plan of action that shocks and upsets everyone.

In the season five premiere, Will and Natalie face the aftermath of a horrific car incident and are left to battle for their lives. An investigation is launched following the suspicious death of the elder Cornelius Rhodes, Dr. Rhodes' father. Maggie receives life changing news. Dr. Charles cuts his honeymoon short to tend to a young patient he suspects might have schizophrenia.

April finds herself in a dangerous situation and Natalie gets an update on Will. Dr. Rhodes gears up for a gala honoring his hybrid O.R. and tries to convince Dr. Bekker to join him.