http://www.amazon.com/Hope-its-Sunny-Out-Meeting-ebook/dp/B00F13MD3I I just read this. Free download. It's a real short and sweet read that addresses this troubling issue. I found it through r/seduction which has also has a lot of useful info.

There's a lot of innocent ways to approach her. You could go with, 'You seem like a friendly girl, so I just wanted to say Hi. I'm kiwidong123'." Or, simply ask her for the time or a random question about anything insignificant. The hardest part is just starting the conversation, and after that weight is lifted, it's a whole lot easier.

If you want to read something that will change your life for the better and get you thinking about yourself and women in a much healthier way, read the book Models by Mark Manson. It should almost be mandatory reading for men.

edit: "Here's an excerpt from that first book: Often my students see an approach opportunity, but they don't take it, because people will see or hear them. this might be on a crowded bus, or a busy park. Their fear manifests through their body language and vocal tonality. Instead of speaking loudly, they squeak in a quiet, embarrassed tone.

If you want to be great with women, you have to learn to NOT GIVE A FLYING FUCK what anyone thinks of you. If you're overridden with social fear, you will be stifled. When you're stifled, it's like wearing a mask. You're not showing the girls your true, confident self. How can you be truly confident if you're worried about other people think of you?

One exercise I use to gauge a students social fear is to have them stand on a park bench and yell, as loud as they can, 'I'm the king of the world!' Most guys are barely audible; some even refuse to try the drill.

Then I get up, and in my loudest voice, a veritable war cry, I yell, 'I'm the king of the fucking world!!!' People three blocks down stop to look at me, shrug, and continue on with their day.