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Raising bar vis-à-vis opposite sex

A recent post by an older virgin asking whether "losing it" to an escort is a good idea, and the subsequent discussion about psychological consequences for him got me thinking about a different question.

Has anyone else, due to shyness at a younger age, historically find himself calculating which women he could realistically be with, all things considered, as a weighted average (pun intended)? Cutting out the bottom quartile (you have to get it up) and the top quartile (to be realistic), and target girls who would appreciate the attention? And then after X years you get an opportunity to sleep with a truly attractive woman, and you realize the experience is much different due not just to the touch, or to the better shapes to hold on to (truly better, not simply bigger), but because your brain is overflowing with hormones from realizing you got the top reward billions of years of evolution have taught the male brain. Suddenly the bar is higher, but it seems unrealistic to proceed to hold it that high...

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