Related: Klaroline Shippers Are Hoping for … They broke up in 1x06, and in 1x10 Elena told Stefan she loved him and they had sex for the first time. Klaus and Stefan first met in Chicago in 1922 when Stefan was a Ripper and dated Klaus' sister Rebekah.In the beginning Klaus did not like Stefan, but this changed when Klaus discovered that Stefan was a Ripper and they became good friends. Yet season six also marks the beginning of romance between Caroline and Stefan, so it’s hard to picture Stefan going back to Elena after that. Stefan and Caroline had their fist kiss on The Vampire Diaries during Thursday night’s episode “Stay,” and boy oh boy did it exceed all expectations. Klaus and Stefan in 1920s. Early History. The Vampire Diaries‘ seventh season is beginning to wind down, and it looks like Caroline and Alaric’s controversial romance might be disappearing along with it.. The first got together in 1x02. Fans were devastated when Damon was killed off on the Season 5 finale of 'The Vampire Diaries' on May 15, but his death means the return of his equally hot brother Stefan!