What I don't understand is...
First of all, I can't understand how Roy was considered a "loser" at school. He was miraculously tall, incredibly fit, and drop-dead gorgeous. Whether he was a psycho or not, high school girls would've considered him the hot, "misunderstood" type (before he killed anyone).
With that said, how was Bo the one who got the flirty looks from the ladies in LA? I know Charlie Sheen was supposed to be a heartthrob in the '80s, but standing next to Caulfield he didn't compare. Maybe if they'd switched the rolls, or had cast someone else as Roy, it would've made sense. Had I been in the bar that Roy and Bo walked into, I would've noticed Roy first, and most likely wouldn't have even graced Bo with a glance.
It's all superficial, I know. But most of the time, especially in high school, looks are a major factor in how people treat you. And Caulfield was sex on legs back then.