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Later Caroline started dating Stefan's brother, Damon.

Their friendship deepened, culminating in a kiss, but Stefan was unsure of how to move forward, given the fact that Caroline's mother had just died, and Damon had planted doubts in his mind.

Shortly after, she started dating Matt, Elena's ex-boyfriend.

You told me once that I would fall madly in love without realizing it. Stefan saves her after Damon attempted to kill her.

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.

It's funny the things we remember out of all the years that go by.

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".

After regaining his memories, when Caroline believed that him and Elena were getting back together, she seemed quite jealous, which was a drastic departure from before, when she always supported their relationship.

Upon learning of Bonnie's death, Stefan told Caroline that he would always be there for her as she has always been there for him.