What I don't understand is...

1. it's an 80s movie where most everyone cast was goodlooking so finding a good actor who wasn't quite "handsome" to play an outsider psycho would've been a challenge
2. they were all graduating & it seemed like the "cool kids" already knew Beau & Roy very well since the 3-4 years of attending skool with them so Roy was probably already known as a psycho/weirdo or loser poor kid...someone to stay away from
3. Beau was looking to score with any women he could so he had his eye out, the film never depicted Roy interested in nor aware that any women were glancing his way...so the camera never noticed, either

and as an aside, I always found Cauldfield to be a handsome guy but oddly dorky in a way

I agree, they were both super good looking. But both their behaviors were repugnant, with Max Caulfield being the leader and Charlie being strung along for the ride even though the majority of the time he was happy to be messing around, if Charlie didn't have Max he would more than likely have a girlfriend and be on the football team.

Roy hated people and probably went out of his way to keep people away, even sabotaging Charlie Sheens attempts of trying to fit in. We see a few times in the film Max goes over the top to ruin the fun for everybody else in social settings, which cracks Charlie up, but without Max he could be pals with all these people.

The only person Max liked was Charlie and he probably wanted to keep it a duo and not an ensemble.

They were both handsome guys but they creeped everyone out and rightfully so.

Those Columbine shooter boys were not at all ugly but were not very ‘popular High School kids’ either.

You can tell when a guy is a danger, and when he’s got a sidekick it’s extra obvious.