To attempt to quickly and deviously fuck people over by any means necessary for ones own personal advancement.
My Machiavellian step-daughter attempted to extort money from me and ruin my reputation when I divorced her mother.
by crappieguide December 30, 2013
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Someone who is extremely good at manipulating and deceiving people for their own selfish gain. Examples of Machiavellians include, but are not limited to: IRS scammers, sugar daddys, e-girls, e-prostitutes, black hat hackers, Donald Trump, your girlfriend (potentially), sketchy sellers on Aliexpress, and that guy down the street who claims he is homeless.

If you are a Machiavellian, please do take note that machiavellianism begets machiavellianism. Research has shown that people who have been psychologically manipulated are more likely to manipulate others.
Dude 1: So I heard you bought some custom videos from this e-girl on Reddit, how'd that go for you?
Dude 2: Extremely bad. I thought she was legit and everything, she even showed me a screenshot of the video, but once I had paid her she never replied back.
Dude 1: Damn dude, I mean I wouldn't have trusted some random internet girl in the first place. The online sex market is filled with Machiavellians, y'know?
by UltimateDoge April 27, 2021
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Negative term used to characterize unscrupulous politicians of the sort Machiavelli described most famously in The prince.
Machiavellianism is completely immoral, but effective to maintain power.
by ChellythebestinMK8 January 09, 2019
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A conscious delay in response for the purpose of not appearing too overly eager to respond.
"I reject the concept of a Machiavellian delay. I think social networking has made this tactic transparent. The new ethic is authenticity, which lends itself to fluid communication."
by shadyladyk March 06, 2010
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Similar to the sexual position, 'the wheel-barrow' (i.e on one's back in a submissive role with the legs pulled over the partner's shoulders) the bottoming person would be either debating, complaining, glaring (or all at the same time) during the entire process.
I was trying to make him comfortable for his first time, but the agitated little shit kept patronizing me and glaring at me. It was probably my fault for provoking him, but heck it was a total Machiavellian wheel-barrow moment.
by Le Emme February 02, 2011
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Demoralizing somebody just enough that doing something to break even seems like a morale boost.
Disney world tells people theres an hour wait when they know the wait is 45 minutes, this keeps the crowds from making the wait an hour wait. People think they're getting something extra, but really theyre not getting anything but a Machiavellian morale boost from someone who tried to jerk them around and waste their time.
by Solid Mantis August 25, 2020
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A manly princess. Not to be confused with a true tomboy that does things guys do, a Machiavellian princess appears/seems to be a tomboy or like a tomboy on the surface, but is actually excessively masculine by nature, and someone you would think would have had a sex change by now, but hasn't done so only for fear of the social stigma. A Machiavellian princess is called a Machiavellian princess in the same way an effeminate prince is called Machiavellian, she is the female version of a Reptilian effeminate prince.
The Machiavellian princess wants everybody back in line.
by Solid Mantis May 06, 2021
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