There's some discussion at GNXP on Machiavellian behavior, in particular as regards its application to getting sex. To expand my comment, recall what the different facets of Agreeableness and Conscientiousness measure. Here is a brief outline. Someone who scores low in Agreeableness will tend to mistrust others and believe they're motivated by self-serving goals, be equivocal or devious in expression rather than frank, have little concern for the welfare of others, respond more antagonistically than compliantly during interpersonal conflict, brag rather than be modest, and be more toughminded rather than sympathetic towards others. Machiavellians probably don't score in the bottom of the Conscientiousness distribution, since they believe in their own self-efficacy (or else plotting is pointless), strive for achievement, practice self-discipline despite distractions, and think things through before acting or speaking. However, personal organization (or Order) and emphasis on fulfilling moral obligations (or Dutifulness) they would score low on. Someone who scored high on Order would have everything in their living space tightly organized, be a neat freak, always be punctual even in informal settings, etc. But to go from one woman to another without setting down roots requires a certain degree of aimlessness and vagabondishness, of course in addition to little concern for the other's feelings. Machiavellians probably wouldn't score as low on A and C as sociopaths would, but this is only due to sociopaths scoring very low on C. Sociopaths are great seducers, too, though, as this item from Steve's blog demonstrates nicely. They are not necessarily serial killers, but they would bilk trusting old ladies out of their life savings (perhaps by seduction) without flinching.
My stance is that Machiavellian plotting is like war (a point that Robert Greene may or may not have already made; I haven't read any of his books). So, it's fine in self-defense and perhaps even in revenge, but unprovoked manipulation I don't support. In most cases, though, it's like learning a martial art just to go out and kick ass on the people you've always wanted to rough up. Similarly, it's one thing to have the low empathy of a misanthrope who wouldn't, say, donote money to charities for poor kids to attend college; but it would be another to actively steal funds from such charities. Of course, I'm not suggesting that seduction is criminal, but simply that it's in the same direction as these activities (pro-actively using others for personal gain rather than reacting to the provocations of others), though certainly not of the same magnitude. I may not care if gold-diggers have their feelings ripped to shreds, but nor am I going to devise a plot to exploit them as they do others. If it were a matter of revenge, then sure; but again, pro-activeness is a different creature in using others. And to be sure, if the others were a social plague, who knows, but I could see myself taking on a Travis Bickle-ish role and flushing some of the garbage down the sewer. The other group would have to be something pretty awful, though -- violent criminals at the least.
Let me put it simply: there are simply too many groups of sub-criminal, vile individuals for me to plot to use them all for my personal gain. I'd rather take the few moments of consciousness I've got to find a pleasant, exciting girl to settle down with, and to find work where I can be left alone by bosses rather than be forced into political maneuvering to advance my status. Again, though I'm pretty low in empathy, I'm not evil; and from all accounts I've read online relating to pickup artists and the like, once you go down that road, your respect for women vanishes. There are plenty of silly things relating to women that I'll never respect: the taboo that surrounds discussion of male-female differences in intelligence (variance) and personality (averages), chick lit and chick flics, their incessant gossiping, and so on. And there are large swaths of Anglo-country women infected with various strains of radical feminism. But there are attractive, agreeable, fun girls out there among whom I'd like to find a mate, and for that to work I have to have my basic respect for women intact -- not viewing them as puppets for my amusement, at the very least. The abyss staring back into you, and all that. Don't get me wrong -- most guys, including me, would love to have anonymous sex with a variety of hot girls if they presented themselves at our door. But in the real world, groupies are not literally banging down your door, so this requires effort, a part of which means you'll view the targets as puppets. I couldn't respect a puppet, obviously, so I would only feel disgusted by their presence, which I could overcome if it were subservient to a goal of revenge, but if I can manage it, I prefer to just avoid loathsome people.
Incidentally, to show how one might use one of Greene's 48 Laws of Power in self-defense, consider this one that I just read in the recent New Yorker profile of him: "Play a sucker to catch a sucker." Last week, some early 20-something guy pounded at my door, and it looked like he was selling something. I hate these fuckwads as much as I do telemarketers, except you can't simply say "Remove me from your calling list." Moreover, you're in a unique spot to cleanse this rot from your entire neighborhood -- not that I feel especially close ties to my neighbors, but I'd want them to perform this sort of basic housecleaning for all if the screwball were on their doorstep. Before I called the police on him, though, I had to make sure he'd never suspect it. I let him talk my ear off about the magazine subscriptions he was selling, purportedly to raise funds for him to attend college and get his life going in the right direction. The more time that passed without the door being slammed in his face, the more confident he became -- so confident that he won't see it coming. I even invited him in to warm up, whereupon he continued with his obvious lies and obsequious complements about how the living room looked.
I still wasn't convinced that I was going to call the cops on him, but something finally set off the alarm -- he claimed that there were other kids selling subscriptions in the area, so if I did end up buying a subscription, he'd give me a tag to put on my door so that the others wouldn't pester me. Only a moron couldn't plan it out so that two kids didn't knock on the same door, and few people who plan things are morons in the sense of having low IQ. That was such a bizarre thing to say, that I agreed to buy a subscription, with the full intention of canceling it once he left. This way, I got his name and company he was working for, not to mention again the effect this had on his confidence and cockiness. So after I signed the receipts, he tore off the thin strip that held the several carbon-copy receipts together and wrote, by hand, "So-and-so's winning, bug off," which I was to affix to my door with scotch tape to let the other sellers to "bug off." Again, only a fly-by-night company would do something so bizarre, rather than have a professionally made "Do Not Disturb"-type hanger that I would leave on my doorknob (again assuming they couldn't just have the kids take non-overlapping areas).
Sure enough, when I Googled the company -- Great Lakes Circulation, Inc. -- I discovered that their door-to-door employees are all liars who spin various heartstring-tugging stories about college tuition assitance, hospital fundraisers, and so on. In reality, they simply sell magazines at roughly 300% the cover price. At least I had the name of the company if I needed to take any action to keep them from revisiting my neighborhood. Even better, though, all that time this doofus spent trying to sell me snake oil allowed me to develop a perfect mental image of what he looked like and what he was wearing, so that I could report his ass in flawless detail to the police. I jumped up and down when I saw the county police cars pulling out of the street I gave them, where I last saw him walking. I knew the police would've told me to buzz off if they were having a busy day, and the fact that they sent two cars to haul off someone who was soliciting without a permit and misrepresenting themselves, just shows how slow a day it was. So I don't want to hear how I prevented them from stopping a murder or anything. Now not only that fucker but his bosses as well know that men with guns will show them the way out if they come around here again. "Play a sucker to catch a sucker" indeed.