The principle of charity is used in philosophy of language and argumentation theory as an important principle of interpretation which credits speakers with “the best” plausible interpretation of their discourse. I contend that the argumentation account, while broadly advocated, misses the basic point of a dialectical conception which approaches argumentation as discussion between two parties who disagree over the issue discussed. Therefore, paradoxically, an analyst who is charitable to one discussion party easily becomes uncharitable to the other. To overcome this (...) paradox, I suggest to significantly limit the application of the principle of charity depending on contextual factors. (shrink)