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There's more to the world than what you know. After Caroline and Katherine finish college together (after the Elena/Silas cure fiasco), they come to some important self-discoveries and go through some major life changes. Who knew that Katherine would be the one to encourage Caroline to follow her heart to New Orleans and to Niklaus Mikaelson. Will Katherine get the chance to follow her own advice? Okay so chapter one relates to Finn/Sage. If he met her maybe 100 years into his vampire life and she was a pirate. (IDK where this really came from, I do remember seeing someone else have a headcannon that they were pirates together though so that's probably it.)
A Pirate's Regret
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