Mr. Dicks, proper success with women can only be achieved by addressing every single aspect of your life in the best way possible.
First I'm just going to draw attention to that username of yours quickly. Sure, it's just a username on a forum but it's a perfect little example of how everything you do has some effect. Chances are you honestly don't care, and that's all well and good - but that does have certain repercussions - if you don't care, why should we take you seriously? Or perhaps you're just putting up the facade of not caring to appear cool, which is a fundamental flaw with traditional pickup. A username like "Roaker1" while possibly strange and meaningless to most people (like my own username) has a completely different effect (or rather, lack of one) than a username like "Ihaveamassivedick" or "penispenispenis" or "vaginavaginavagina".
Anyway...
From your first post your problem is clearly this - you're too hung up on fear, or "being rejected", like if the girl doesn't respond favourably, it's the end of the world. You're not even willing to try it once.
More importantly, this says you aren't regularly experimenting face to face by starting random conversations. It's hard, but that's the point. You're doing this till it becomes easy.
And you imagine this means getting used to a girl going "get lost dweeb!" and then feeling "I could never get used to that, that's going to hurt every time..." no, that's not what you're getting used to.
You're goal is to be getting used to talking to someone in such a way, that if they're not interested, it isn't a big deal - take this example;
You: "You look gorgeous."
Girl: "...hahah... thanks..."
You: "Sorry I just had to say that

Where are you off to today?"
(short interesting conversation)
You: "I really got to go now... what are you doing this afternoon, would you like to catch up after work?"
What actually happens at this point is ENTIRELY DEPENDANT on how your body language, tone of voice, etc. the vibe you were giving off and her interpretation of it.
Your problem in the past has likely been you've come off too much like... you're trying too hard to be "attractive", you're really hoping to get her number - this colours all your actions and
it doesn't matter what you say, girls will feel this and respond "Yeah I gotta go..." or "get lost dweeb!" and they have every right to do so.
Get out there and talk to people like you're just having fun. Practice it.