The quintessential ladies' man - which I, admittedly, am pretty fucking far from - shows fabulous success because most women are mostly the same in fundamental ways. Think about it, if every women were truly her own snowflake then what commonality could he exploit; I decline to accept this, women have many of the same wants and insecurities; I simply do not have the time, energy, or lack of compassion to exploit those insecurities on a daily basis.
QFT, that.
See, the fucked up truth is that all of human mating and courtship basically comes down to economics, game theory and probability. Which is to say that no matter who you are or what you're doing, you're just playing the odds and doing things to try and shift those odds in your favor. Some people are in high demand because lots of people want them (to fuck, to date, to marry, whatever), while others are in the opposite position. Likewise, someone who is in high demand can be fickle, choosy, and equally demanding of their clients. Someone who is in the opposite position has to hope they can pay more than anyone else. Not monetarily, necessarily, but in social status or dick size or offer of novel experiences or something else. Men would seem to have higher biological sex drives than women, in general, which basically means that men need male-female interaction more (for this at least) than women do. Hence while any one girl may go out with fifty different guys a week, overall women act as the choosers because they're on the supply side and we're (males) on the demand side. Obviously in any particular situation it could be the guy or the girl in high/low demand, though. (Now that I think about it, I suppose each person probably has a unique time-dependent supply-demand curve associated with them.)
That's the econ part, the probability part is because the obvious truth is that there's no one person out there you were meant to be with or anything, any given person just ranks everyone else according to how desirable they are to them, which is obviously affected by the economics/supply issue. Someone might be great at the time, but then if your position in life changes and suddenly another hundred "better people" want you, your rankings might change some. The less picky you are then the better chances you have of meeting someone, so it's just a matter of running through as many people as possible until you find the optimal thing. So honestly, while people don't like to admit it, you're a lot better off just mindlessly playing the numbers than trying to focus on specific people who seem better than the mob or whatever.
The game theory part because, unless you're in high demand, then you have some competition. Hence you can obviously skew the odds in your favor by applying more successful strategies than the other guys, like dealing with many of the desired sex superficially vs. making a concerted effort towards few specific people. Well hell, if you even watch
A Beautiful Mind (movie), the specific example they use to demonstrate a Nash equilibrium involves
dating picking up chicks at a bar. I'd argue that this is largely what the "player" types do: create high demand through successful applications of game theory, whether they know it or think of it in these terms or not. I mean it would seem superficially rational that a girl would like a smarter, richer, better looking guy who was nicer to her 100% of the time, but when many guys are trying that then the one who acts like he doesn't give a fuck may win out simply by applying a unique strategy.
That's my grand unified theory. Emotions and horniness just fuels the entire thing and obfuscates what's really going on at the same time - after all, if nature hadn't bred that into us then what rational person would ever put up with all this shit. But I think the behavior of everyone involved is pretty well explained by the above. People need to understand that so they don't end up really pissed off by thinking this was ever a level playing field in the first place, which is what happens when people pretend like this is about love and romance and "finding someone special" versus, well, the fact that all people are whores just looking to get the most they can out of everyone else.