I used to be a shy guy, probably much like yourself I imagine.
I'm an engineer by training but there's no work in that round here anymore, I didn't ned to talk to people to do that job except in technical terms which was easy. But talking about mundane every day things just didn't work for me..

I started working in a retail store, part of the job is talking small talk to people, difficult at first but my confidence soon grew, now I'm the top performer in getting people to have our store cards because I can talk to them and persuade them..

I guess what I'm saying is, you do need to practise to become comfortable and then it will come easily.
It sounds like you are maybe trying too hard, you can't just walk up to somebody and start talking to them, they will think you escaped from somewhere..LOL. Best way is to maybe sit or stand by someone where there is a point of interest you could start talking about, say in a coffee shop, talk to the person at the next table about how good [or bad] the coffee is or in a shop talk about the goods etc...Once a conversation starts you can take it on from there.
Give it a go, just don't try too hard or you will come over as a bit of a nutter..LOL.

Injustice will be avenged.
Cofiwch Dryweryn.