All men by nature desire to know. When it comes to questioning on the "meaning" of things, as you should do, it is better to consider their "relevance". Relevance is a practical notion of meaning particular to you. The more crucial aspect of learning game is to know very well why you are learning game, going out, and trying to get laid. What is your true motivation? Idealism (metaphysical meaning) is great and all as point to strive towards, but it may simply not be exactly relevant to you at your point in life and thus not a sufficient motivation. Without satisfactory motivation or purpose, your activity will be hopeless.
How can you apply this? Sit down and think, for as long as it takes, why you want to get laid until you feel you have reached a satisfying understanding of your purpose.
One thing among many for me is that I've realized that I had a sort of "self hate" for not having a voracious sex drive, "pit bull tenacity", and being unable to freely express my sexual desire. I've always felt myself different from others in this way and being less than for it. The daily stress of this lack would drive me to damn near suicide if I was unable to figure this shit out. Regardless of the truth of the matter with respect to how other people actually experience their sex drive and so on, this notion of myself was extremely relevant and in connecting with it by being honest with myself, I found the proper congruent motivation for carrying an interaction all the way to sex in spite of very basic fear, uncertainty, and doubt.
We are drawn towards pleasure or away from pain. When you are in your head by default, stifled, neurotic as most people are, the escape from pain is the far more relevant motivation, as unideal and un-Pookish as that may be. I knew full well that if I was unable to express my sexual desire, my life would be an endless cycle of pain. I could go on about the catastrophic scenario painted in my mind but I'll save that for my hard drive. The point is that this motivation was relevant to my mental state and my self-concept and my history and so on and without that sufficient relevant congruence, I would have never pushed beyond my comfort zone.
"The unexamined life is not worth living," spoke Socrates. "Know thyself" is written at the Temple of Apollo at Delphi. Be shameless in sitting down, spending the time to introspect, and being honest with yourself about who have grown up to be, and what it is that you want and more importantly do not want. Write it all out. You will know when you have struck gold because you will get up, go outside, and make it happen. The information you need will make itself apparent to you. It will simply make plain sense to you because it will have become completely relevant and resonant with you.
Your truth shall set you free.
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