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You need to get into some random fights. Your adrenaline will pump and you'll get the fight or flight feeling at first but if you fight often enough you will become a bad ass and it also will help transition you into a pimp cuz you shouldn't hesitate in anything you do.
This is total bullshit. Don't take this advice. Let me explain why: - "You get in a random fight. You get the shit kicked through you. How much more confident do you feel now? Lying down face first on the pavement will surely give you that much needed confidence.."
However, the majority of what people on here has said is fairly solid advice. I've been in the game for quite a while now, and the one key thing that I could say has helped me gain confidence is reading new material, then going out and practicing it. If it's successful = more confident. If it fails = me reading more, revising my strategy, going out again till I do get successful. Bear in mind that everyone has a different approach to gain confidence, and it doesn't happen overnight. Heck, I'd like to be a more confident person than I am now.
One more thing, don't confuse arrogance with confidence. Arrogance is a "fake" way of obtaining confidence, eg: it will make you feel better about yourself, but it's a total turn-off when it comes to the girls. (I'll point out, that every girl is different, and some may like it, but I'm talking about the majority here).
I'm familiar with Style's Rules of the Game, and although I reckon it's kind of lame eg (don't take a shower for one day, and see if anyone notices... wtf??) Hey you could use a laugh and a good time, I enjoyed myself for some of the challenges. Make sure that you do ALL of the exercises if you do go through with it, even the ones where you have to write out paragraphs, because its useful later on.
So yeah, that's about all I have to add. Confidence takes time to achieve, and it's more of a soul-searching kind of thing, rather then someone giving you advice on how to get it. You need to figure it out on your own, because its all in your head. Just got to put the pieces together. I wish you the best of luck.
EDIT: Quote of the day:
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Grab life by the tits and fuck that bitch cuz this world is a giant pussy waiting to get fucked.