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His entire sense of self is dependent upon girls telling him how he is such an "amazing guy" and he is "the best" at sex. Because he lacks self-esteem, he is unable to be with one of these girls once they realize that this "amazingness" is just a facade and that deep down is he just a flawed person like the rest of us. Therefore, all his energies are put towards the conquest of girl after girl and his life is reduced to nothing more than that of an immature cad.
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