Damon and Bonnie didn't know why they were sent back in time or by who; just that they needed to accomplish whatever it was they needed to do and get back to their own time. Now with them bouncing around the past trying not to change the future for themselves or the ones they love the stakes are higher in this game of why, how and when and to get home sooner rather than later.

While recruiting Bonnie to join their road trip to Chicago to retrieve Stefan, Damon is lured into a trap set by a former lover and cursed to desire the one thing he believes that he cannot have, while Bonnie is caught in the crossfire.