Dean Winchester may have had the reputation of the popular guy who sleeps around with every girl, but he definitely did not have the reputation of being a dick. He was one of the most caring guys in high school, always looking out for the younger kids who got bullied (which may have been why all the girls would fall for him so easily). When Dean stands up for an older guy with a strange name from getting picked on, he never expects for the guy to have fallen for him. Literally.