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With something as complicated as dating, with so many random factors involved, surely the probability of anything happening or not happening is about equal? Everything from physical characteristics.. "too short, too tall, too black, too white".. to positioning, chance, demeanour, etc etc.
What you describe would further the argument that the probability is not about equal or 50% in relation to dating. If you are able to control and minimize some these various factors, then maybe you could say the probability of success is equally likely as not likely. For example, people tend to marry those with similar IQ levels, therefore we would assign a low probability of success if one person has an IQ of 145 while the other has one of 90. Good looking people also tend to pair off with other good looking people, races by and large tend to marry within their own race (although this trend has fallen in recent times). Aside from that, you must like the person, and they must also like you, which is another whole factor that alters probabilities. Because there are these factors, if you saw a random person you think you like, and you aren't controlling for anything special (i.e. you did not see this person at a Mensa meeting), then you probably should assign a lower probability of success considering all these factors. The more information you know, the more the subjective probability changes from the first more random one and the more accurate it becomes. Unless of course, you're a Bayesian in which case you should assume the prior probability as the correct one.