October Kingsley

Elena is surprised to receive an invitation to a formal ball, and when Damon and Stefan hear the party is being hosted at Klaus’ newly renovated mansion, they both insist on attending the event with her. Caroline and Matt also receive invitations to the ball from unexpected admirers. At the elegant party, Elena learns of a horrifying plan that could lead to numerous deaths and she must decide who she can trust with her new information. Caroline discovers a side of Klaus no one would have suspected. Finally, after an evening of violence and dashed hopes, Damon finds a new way to cope.

This special black-and-white episode gives a nod to 1940s-era film noir as Spencer's numerous sleepless nights with the help of prescription pills start to take a toll on her, as her hunt for Ali and much-needed answers continues. As she pours over newly acquired information, her world view takes a turn into black and white. Now teleported into the world of film noir, Spencer tries to come up with the answers she and her friends have been desperately looking for. But in this world of fedora hats, switchboards and 15-cent coffee, can Spencer finally put all of the pieces together that lay in front of her?