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i read that book too, he suggested picking up the phone book and calling random strangers and asking for some make believe person. Then once they say that person dont live here, you start with questions like "hows the weather" or Have u seen any good movies lately"
its not to pick them up just to get talking, being social. It's not a terrible suggestion either, it makes talking to the next person that much easier.
another thing is to simply say hi to every woman u see. on the street, in a mall, in a bank, at school. library etc.
those are risk free chances to get over the shyness, the worst the woman can do is roll her eyes and walk away.
I find about half of the women i say hi to during the day will either smile, or say hi back. some will look the other way, and some will make a dramatic run away, as if u were following them, anything to make themslves believe everybody is after them
i find approaching women during the daytime, is much easier than at night, cause their defenses are down during the day, they dont expect to get hit on as much and will usually at least be nice.
give it a shot, it does work and makes u feel a tad better about yourself when they smile back.
Oh man you just reminded me of what I used to do with the phone operators (females) whenever I was on hold with them on the line. I would ask what state they live in, married, weather, etc... good times!