dclayh comments on Honesty: Beyond Internal Truth - Less Wrong
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I've heard from many sources that con men are actually among the easiest to deceive. The rationale seems to be along the lines that con men have utter contempt for their marks, and therefore once a con man thinks of you as a mark he'll be oblivious to any signs that you're actually the one playing him.
(I've also heard, separately, a saying to the effect of "It is difficult/impossible to deceive an honest man", but it comes with no justification other than perhaps a religious one.)
del
I recall watching a television show just as microexpressions were receiving pop-science attention which claimed that tests against videotaped gold standards showed that the only people who were reliably able to distinguish liars from truth-tellers at a rate above chance were either people explicitly trained to detect microexpressions or professional spies.