In order to deal with their recent trauma, Emma suggests the students participate in a group simulation that transports them to a film noir world. Hope, Josie, Lizzie, MG and Rafael quickly learn they must confront their conflicts head-on or risk facing the game's catastrophic consequences.

When things take a dark turn on the twins' 17th birthday, Lizzie is left to make a difficult decision. Meanwhile, Hope takes drastic measures when she and Alaric clash over how to handle an issue involving Josie. Finally, Rafael makes a heartbreaking discovery.

In a race to save Josie, Hope infiltrates her subconscious and finds herself in a fairytale world filled with dark magic. Back at the Salvatore School, Alaric, Lizzie and the Super Squad commit to their own risky plan to get Josie back despite the potential consequences.