The truth is, they only want guys with a lot of money to approach them. It's not as much about looks as it is about money. I'm sure women don't care when Hugh Hefner, or another old, wealthy person approaches them. On the other hand, there are guys with the "ideal" gym body, and girls will ignore them if they don't have money.
It's the harsh reality, but women in their 30's, and older are better. Most young women are closed minded.
Well some times if a girl wants a certain guy to approch them and the wrong guy comes up well they can expect to not get eye contact be shrugged off. Unfortunatly im guilty of this action but in the last few months i relized that just because the guy you havnt pin pointed approaches you dosnt mean this guy dosnt have feelings and that there could be an amazing friendship lying just beneath the surface of awkward.
I don't think the paradox you came up with is very realistic. Women aren't going to label attractive men with lots of things going for them as desperate creepers. Obviously at times, there are actual creepy dudes that try, though.
Unfortunately, often times, women use the creepy tag on an otherwise normal, well adjusted guy, who just happens to be not attractive enough for them. I remember a girl on here asking a question that basically amounted to declaring a guy in her class as creepy because he would occasionally sneak in some quick stares. How dare an unattractive guy glance at a cute girl!
It seems to me like some women just want to avoid being labeled as shallow or something, so they try to flip the whole thing on it's head by instead making it seem like these guys are creepy and at fault for playing the game properly and having the gall to approach a women who was apparently too good for him.