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In Season Two, their relationship changed due to Caroline's transformation into a vampire. Shortly after, she started dating Matt, Elena's ex-boyfriend.Notably, they have always been able to help each other with the other's relationship problems.Caroline always supported his relationship with Elena up to the point where she herself developed romantic feelings for Stefan. The relationship between the cured vampire doppelgänger, Stefan Salvatore and the vampire, Caroline Forbes. In Season One, Caroline felt an attraction for Stefan, but he rejected her immediately because he was interested in Elena. I remember how you told me that when I was ready for you, you would be ready for me. I think a part of me has been ready for this day since the moment I first saw you, the new mystery guy in the hallway at school. A hundred years from now, I will remember this moment for the both of us. You told me once that I would fall madly in love without realizing it. Stefan saves her after Damon attempted to kill her. Later Caroline started dating Stefan's brother, Damon.
In Season Five, when Stefan lost his memories due to a spell, Caroline was the only person that he trusted immediately and he also blatantly flirted with her on at least one occasion, telling her she was "much hotter in person".Stefan succeeds and after feeding on a bystander victim together, the two have sex for the first time.