Sorry for the late replies, but I am currently out of the country, not having access to the internet or a properly working computer.
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If you don't care about sarging girls then and you just want to have fun with your friends, then I assume you don't open girls? I can't imagine that you approach and open girls if you don't give a shit about them at the moment. To my own experiences: no matter how much fun you have with the guys, girls will not just start approaching you, especialy if your in a club or a bar where you only know your mates.
Secondly, most people are aware that you should adopt an "I don't give a shit attitude" to increase your confidence. But the question is: how do you make yourself congruent with these toughts? How to truly believe it? It's like you said, thinking "fake it till you make it" doesn't work. If I understand you well there was just a moment in your life when caring into game and what others thought of you turned into not caring at all?
To answer your first question - Don't get me wrong, you DO open sets. However, you do it while you have fun with your friends - spontaneously. If you see a chick doing something funny or weird, you got yourself a good opener right there. Start busting her balls. This one time, a chick almost caught her hair on fire (and she would have, if I didn't save her lol). Not saying these kind of things happen all the time, but the point is - open sets while having fun. Dont force yourself out there if you feel like its all work and no play. Hope you get my point.
The attitude will develop itself the moment you are comfortable with who YOU are and the moment you stop caring what others think of you. You need to motivate yourself to think along these lines - or your whole life will be shackelled in chains.
The moment you actually feel comfy with yourself - everything else will follow (the confidence, the i dont give a shit attitude, and practically anything else that is GOOD).
Question is, how much do you truly care of what people think of you? If you care the least, make it go away. Here is a fact for you - people in fact DONT care about anything you do or act like, because they are too busy thinking about themselves and how people view them.
So even if you feel that you have screwed something up... trust me.... it is a tiny detail that no one even pays attention to - no matter how significant it feels for you.
Hope this helped,
Panda.