As a new years resolution I told myself that I'm going to live life without hesitation, without caring, without giving a fuck. As a start, I began having small talk with everyday people (customers, cashiers at stores, waitress etc.) I'm even planing to go to karaoke bars to sing (I'm a bad singer) to help me simply not give a fuck but there's always something that holds me back, something that makes me think for to long and hesitate.

My question: Is there something I can do to get over this (activities, lines, etc.), is there something I can say to myself basically saying I have nothing to lose?

So you don't want to give a fuck? Here:
http://inoveryourhead.net/the-complete- ... ng-a-fuck/

That should be a great start. It sure helped me when I first read it.

For one, I think you need to change your mentality. Instead of worrying about people and their thoughts of you, try to put those out and not worry about them. Many of the people you meet, you probably will never see again. So just keep pushing yourself and you'll eventually will get there.

i know this sounds like it sucks, but getting rejected a bunch of times will do wonders for not giving a fuck. if you were to go out right now and do 20 approaches, some of those girls might tell you to fuck off. it's embarassing and it stings, but it makes you stronger every time it happens. if i went out and approached 1000 girls, and they all shot me down, do you think i'd give a fuck after number 999?
also, what's helpful is getting a job where you work with people. you are constantly exposed every day, you will start to become desensitized. try doing sales or retail. anything where you have to talk face to face. specially with sales, you will come to accept hearing "no". you'll realize it's not as big a deal as you may have thought.

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I'm an Ultra-Dork Neurotic Creeper who vlogs about approaching hot girls in da club.

WARNING: i have a sick mind...
http://www.youtube.com/playlist?list=PL ... dI-kuvLf2G