You have to understand that in our culture, men are supposed to initiate courtship, and that's the way it goes ninety eight times out of a hundred, probably. If he's interested in you, he can't wait for you to show interest. Because he's most likely gonna be waiting forever before he receives any sort of unambiguous signal.
Sure, some girls think they're being too available by giving an indication of interest that is actually detectable by guys. Personally, I always find that an early, quick wink gets things moving along.
So he has to just go for it, and then find out afterwards whether or not you're interested. It's like a coin toss.
I think most girls make it clear enough whether they're interested or not. I know guys sometimes struggle with social cues, but even then, when a girl is playing with her hair, laughing at your dumb jokes or smiling at you, chances are she likes you. If you're not incapable of reading body language, I reckon it's more like an 85%.
If a guy never asks a girl out, he will die single and alone. And that's something most people would prefer to avoid. Since the probability of being rejected is high, he usually has to ask out several people before getting a match. By "several people" I mean whatever women he's had enough contact with to deem a potentially suitable partner, who potentially might show interest or willingness to him. A woman who he hangs out with a lot would probably be near the top of that list.
I don't think the probability of being rejected is high at all. I think that if a girl is showing interest in you, you'll wind up with her like 85% of the time. You shouldn't be just randomly approaching girls. You should be waiting to read their body language, and then responding to that. A woman who hangs around him is more likely to just want to be friends, elsewise she'd give some pretty overt indications of interest (I know I certainly would).
Some guys just never have the guts. Other guys take almost any ambiguous signal (such as a polite smile or polite laughter at a half-@$$ed joke) to mean a yes and so they go for it, no holds barred. Because when two people of the opposite sex interact, communication difficulties can easily ensue.
Courtship is very often preceded by friendship. It can sometimes be difficult for a guy to tell when trying to take things to the next stage is inappropriate (again, miscommunication), unless she tells him off the bat, which she might feel to be too awkward a conversation to have (and so she doesn't).
If a guy continues to attempt courtship with her after this convo has been had, I'd have a lot less sympathy for him. I'd also have very little sympathy with a guy who started out with "Hey, wanna bone?", though forgive me if I'm skeptical of the claim that anybody either here or on DDO did that to you, except perhaps out of malice (the reasons behind which should escape no seasoned user here).
Yeah I think not only some guys are just too shy, but most guys. It's like they need permission to take the relationship anywhere. All you need to do as a guy is gradually increase the intimacy of the interaction, and it becomes pretty clear what stage you can take it to. If you're met with a firm "no" (not a playful no), or body language which shows that she's uncomfortable, you've reach the stage that she's comfortable with.
The guys who ignore overt rejection, or just skip to a whole heap of intimacy, aren't going to be very successful.
Your best bet would be a guy who's in a situation where he's not looking for somebody, though among people of your age finding a male person in that kind of situation is sort of unlikely. Many are generally apathetic towards dating but would run with an opportunity if handed to them. Just approach one of those guys, signal interest in friendship only, and poof. There you go. Platonic thingamajig established.
Oh I'm not desperately looking for male friendship.
Women don't have to worry about finding a mate. Guys will literally flock to them, and then they pick one. So many guys, in fact, that they complain about it. Save an exceptionally unattractive woman, not being able to find a mate is something that women usually aren't going to have a problem with. So as for those guys who seem to always be pestering you, you can't understand where they're coming from. You'll never have to deal with rejection, or being alone. A ton of guys would give an eye and a limb to be in your shoes. So don't be so quick to judge, ladies.
This thread was more about friendship between men and women, rather than courting realities.