I'm generally an introvert, but I can function fairly well in social situations (being an introvert just means that prolong social contact tires me out; extroverts get invigorated by such contact).

One of my biggest weaknesses is the inability to go to a bar by myself. There's a bar near my place, and I know the bar tenders a little bit; and it often has the kind of women I'd like to get to know. But for the life of me I can't get the courage to walk in, plop down on the counter and start working the crowd.

One of my blockers is: how do I keep myself occupied? I am bad at just walking up to someone and start chatting; I need a reason to do so (get a drink, point out something salient on the dress, etc.).

Any tips, pointers, etc. would be appreciated.