Title: The End of the Affair
Air Date: September 29, 2011 at 8:00 PM PDT
An unlikely source sends Damon and Elena to Chicago as they continue to track Klaus and Stefan. The Ripper will confront his own past, when he did something really monstrous in 1920s Chicago. An old love interest of Stefan’s named Bex is introduced via a flapper-era flashback. Meanwhile, werewolf Tyler starts to worry about Caroline and looks for help from Sheriff Forbes.