Klaus and Stefan arrive in Chicago where the latter reunites with a woman from the past who still has interest in him, while Damon and Elena follow their trail.
Klaus and Stefan are going nostalgic in the upcoming episode of "The Vampire Diaries". The former takes the latter to Chicago to bring back memories of the good old ripper days. Also there, Stefan is reunited with a vampire who hasn't really moved on from her interest in him decades earlier.
In a flashback to Chicago in the 1920s, Stefan comes face-to-face with a shocking chapter from his wild past. After Damon gets a tip on Stefan and Klaus' whereabouts from an unexpected source, he and Elena follow their trail although their last plan to find Stefan did not work well.
Back in Mystic Falls, Tyler is concerned about Caroline and turns to Sheriff Forbes for help, but Bill might have an extreme way to "fix" her. Damon, meanwhile, upsets Klaus when they have an encounter.
"The End of the Affair" will air Thursday, September 29 at 8/7c on The CW. Claire Holt of "Pretty Little Liars" will guest star as the woman from Stefan's past.