The reason Ross calls Dean a sheep (Coward), is because of something that happened when there were in high school.
Ross had been Dean's underclassman, and they were the most handsome boys in the whole campus.
Ross was intrigued by Dean despite him not being player, and he wanted to recruit him into his father's Castle Guild.
But that all ended one day, when Ross asked his anti-social senior a personal questions.
– Senior, why don't you have a girlfriend at school?
Ross had been curious about this fact, since many girls proposed to Dean, but he would always find a reason to turn them down.
Dean didn't mind much about his junior asking such a question, and he decided to be honest.
– That is because I already have the most beautiful girlfriend at home.