Daybreak Medley

This story is about a male protagonist and female protagonist couple who reincarnate again and again into different persons during the same time period to form a team of heroes to fight against the forces of evil, and how their destinies intertwine and how their relationships pan out.
He will always start out as a loner and social misfit with the saving grace of some talents, and she will always be the beautiful and popular unattainable target, and fate will decree that they will end up together after always pulling them away from the wrong people.