Chatting up complete strangers

My dad likes to do it, maybe part of his nature.
My friend seems to have a gift for it which makes everyone get along with him fairly well, which is why I became one of his good friends since the start of uni. I met him through a friend and he initiated everything (eg. add me to msn, talk to me first, etc.), otherwise I wouldn't bothered to have known him.

I don't bother talking to other people very much anymore, because although I've made my best and closest friends through initiating conversation with them one day randomly, I get the feeling it's because they're the kind of people that are nice to everyone and wouldn't particularly decline a conversation. Plus, I can tell when people don't bother to want to know me better which happens a lot, especially, friend of a friend situations. I think mostly past experience has deterred me from chatting. That plus, I'm a shy person.

How ya doing, buddy?