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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.
During Caroline's mom's funeral ceremony, Stefan overcame the doubts in his mind and realized that he had developed deep feelings for Caroline - referring to it as being potentially "something even better" than his previous romances, even if he could not quite define them - but after the service, he arrived at her address too late to tell her since she had already flipped her humanity switch in order to cope with her mother's death and in the belief that her love was unrequited.
She was the person who revealed to Stefan both that Elena was sired to Damon and that Elena had slept with Damon.
Stefan, on the other hand, comforted Caroline during the emotional fallout of her sleeping with Klaus.
They decide to attend The "Heaven and Hell" ball where they force Nora to siphon the spell off of Caroline after threatening Mary Louise's life.
Later Caroline started dating Stefan's brother, Damon.
Caroline gets released by Lily but still had "vervain skin".
A few days later, Stefan and Caroline still cannot make physical contact and try to convince two of the heretics, Mary Louise and Nora, to siphon the spell off of Caroline.
Stefan and Caroline share their secrets and always help each other.
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".
Were Married, Husband and Wife (Stefan died, leaving Caroline widowed); Best Friends, Former Allies; Sexual, They were in love with each other, Cared about each other, They were willing to start a life together, Caroline will always love him. He became her mentor, teaching her how to control her emotions and thirst for blood.