I am 28. I live downtown in a major city in one of the best neighborhoods in the united states. I make well into 6 figures and have a great job. I went to an excellent private school. I have no problem talking with people, making conversation or leading groups but I cannot and I mean I cannot pick up girls out at clubs/bars. I do work in a heavily male dominated industry and have few female interactions. I am just not sure what to do or where to start at this point. In the last year I literally spent around 50k (usd) at strip clubs, and I get what I pay for in terms of pay to play stuff but I don't just get girls who are into me normally that I can approach and pick up myself at a normal lounge, bar or club. I just can't understand it. I am constantly overcome with extreme anxiety approaching really hot chicks -- even when im sitting at a table with a bottle of ace of spades, clearly the "highest value" person in a club. When I finally do work up the courage to talk the girl I want to its like I am a 5 year old kid. It's really debilitating, frustrating and most nights i am out, I just end up talking with my friends in my comfort zone because of my huge fear of rejection. My job includes taking huge financial risks, but I can't even take the smallest social ones out at clubs/bars. I really don't know what to do guys and any advice would be appreciated. Books, maybe a group or something, anything. I just need to grow up in this one aspect of my life that is completely lacking and I hope this forum can lead me down a path where I can develop.