In Fernando de Rojas’ La Celestina truth and truth-telling are dangerous activities that could lead the characters to be harmed or killed. After Michel Foucault’s 1983 series of conferences and classes at the University of California, Berkeley, and the Collège de France, parrhesia, the freedom to speak the truth, has become an important literary tool through which literary critics understand the way in which individuals interact and manipulate the truth. In Celestina, all characters are aware of the danger of truth-telling, and Celestina converts the truth into an art form. This study shows that Celestina was aware of the perils involved in conveying the truth, particularly when she spoke with a member of a higher social class. In order to circumvent the dangers of engaging in truth telling, Celestina makes Melibea, a noble lady who could harm her if the truth offended her sense of honor and chastity, enter into what Foucault called a “parrhesiastic contract”, which allowed her to tell the truth without incurring any danger. After telling the truth, the parrhesiastic covenant saved Celestina from an imminent death—even though she died as a direct consequence of her pandering for Calisto in Pleberio’s house.