Dipper didn't know he was masochistic until Bill took over his body, because being as if he were a ghost did not mean he still couldn't feel pain. Which he could. And when Mabel called Bill inside Dipper's body Bipper a warm fuzzy feeling began to form. He had always was liked powerful beings and giving over control. But later in life he felt conflicted by the emotions of the good and evil aspect of it all. But after a while Dipper learned not to care about good or evil but just to care about feeling like he had been worthy of someone or something.

Bill had almost always found Dipper cute for a human that is. But when Bill takes on a human form three years after they leave Gravity Falls he finds a friend in Soos who helps him understand this strange feeling inside him. That he would always get when torturing people and sometimes even other demons—he was the king of demons after all. But Soos helped him figure out this feeling was more than a liking for the boy it may actually be love. He just had to figure it out for himself.