Confidence is the key, the key to most things really. I just speak to woman as if they're one of my mates, it seems to catch them off guard & get intimidated putting yourself in control. Initiating conversation is half the battle LOL
If I'm with a group of friends & I see a girl I fancy, I like the line "Me & my mate were discussing something (eg. what woman want in a man) & we'd like a womans opinion" You'd be surprised how quickly they rip into that topic, & that pretty much gets the ball rolling
I once heard a quote along the lines of "Most men want to be more successful with woman. & you know what they do about it? NOTHING!"