Beginning in the 1990s, the medieval historiography has devoted increasing attention to the presence of thought experiments in the medieval philosophical sources. Following the line drawn by King, Perler, Grellard and Marenbon studies, this paper aims to use the concept of thought experiment as an historiographical category to explore the issues of Peter Damian’s dilemma, in the chapter I of De divina omnipotentia, about the capacity of the divine power to restore the virginity of a maiden who has lost it. In this perspective, the case of the virgin appears as a counterfactual scenario, that makes us understand how the question is not metaphysical but fundamentally epistemological. Peter Damian is not discussing about possible boundaries of God’s nature: he is rather arguing about the inability of the dialectic arguments to explain the omnipotence, in an attempt to define the cognitive and linguistic modes under which the human intellect could comprehend the virgin’s dilemma. The crucial step is the shift from possibilitas – intended as a statistical approach to the possible as “potential” – to potentia as a metaphysical attribute, regardless of her actualization: in this way, Peter Damian lifts the question up from the level of the human will, which often fails to grasp his objects, to the divine form of the will, which unfailingly achieves his objectives.