I used to be so frozen approaching women cold, if my intention was to pick them up. Which is odd, since I am a total extrovert. It was probably the one area where I had at that time not been successful when it came to talking to people.
I met girls online, which got around the cold approach, had a couple of shorter things then a long term relationship, which then went belly up. Then I was back at square one. What I did to break out of it was not to approach with the intent of picking up - but with the intent of just talking, then seeing where it goes. Trial and error, and making yourself think not every interaction is high stakes.
Then I cold approached a girl and one of her friends at a bar, started a conversation with that girl as her friend wandered off, got her number... fast forward just over 2 years, we are engaged and will be buying a house soon.
All I would say is pick an environment/situation that is comfortable, be authentic, talk without an agenda and see how things go.
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