Here's the deal. You need a friend/friends who can help you break the barrier. You'll always be more comfortable around your boys. Go to a bar/some party with a friend/some friends, drink a bit to loosen up, and talk to girls. Don't talk to them with the intention of banging them out, but talk to them. It will help you. Do this a few times. Alcohol is a great social lubricant, USE IT.
Find a girl attractive? Get a few drinks in you (know your f***ing limit! If one or two will get you buzzed, that's fine. DO NOT get smangered out. Just a little buzz), talk to her, find common interests. Find out what kind of music she's into, movies, sports, activities etc. Just a little bit, don't pry all crazy. Gauge her personality. Not digging her? Cut the small talk down, and make an exit. Digging her? Get her number, and TELL HER (don't ask) that you want to take her out to dinner sometime. That is all. If she's down, you'll get her number. Wait a day or two to text her. Text her, tell her something along these lines: "So I'm thinking italian, this Saturday. You free?" notice how I didn't ask her, I made a suggestion. Women like confidence. You're not being bossy, or a d**k, you're showing her that when needed, you can be assertive, and that you are confident (even though you're still working on your confidence, this will push you in the right direction). If she's free, and down, you are on your way.
Blam. As crash said, women like karaoke! It shows them that you can sing (women love it, trust me. I'm a singer, and even though I don't sing much other than with my band etc., when I do acoustic stuff, women get all 'OMFGGG BANG ME OUT'), and that you like to have fun. It also shows that you have confidence in yourself. I would suggest going out and doing karaoke with a few guy friends first, so that you don't look like a stuttering fool in front of some chick you are interested in.
OH, one more thing. That girl you are interested in, that you're good friends with? Yeah not gonna happen. You're in the friendzone, and there is no coming out of that s***.
I'm comin up on a year without dicking down. At first it was driving me crazy, not so much now. I may smash on this girl, though, just because I know she's down to get the guts beat. I've got so much stuff going on right now, that it's not on my list of priorities. I don't have time to think half the time haha.