What does it mean to wear a mask?

If first-order empathy is the ability of Self to take into account Other’s point of view, then second-order empathy may be identified as the ability of Self to take into account Other’s point of view as including a view of Self. Considering that a hearer may choose between a first-order empathic and a second-order empathic interpretation of speaker utterances, second-order empathy introduces a pervasive indeterminacy in speaker-hearer interactions. The paper introduces this ambiguity potential in terms of the semiotics of face mask wearing during the corona pandemic, and then extrapolates the ensuing pattern of interpretative options to representative speech acts. The interaction between degree of empathy on one hand, and on the other the convergence or divergence of speaker and hearer beliefs is shown to yield six basic interpretative configurations: assertion, mistake, agreement, disagreement, irony, deception. Recognizing this ambiguity potential of second-order empathy is relevant for linguistic intersubjectivity research and post-Gricean pragmatics, and for the psychological theory of mind paradigm.