Against the background of Gadamer's hermeneutics of trust, for which the primary concern of the hermeneutical enterprise is the matter under discussion, the Sache, this essay raises the question of Gadamer's treatment of irony. Gadamer and Gadamerians have criticized the hermeneutics of suspicion—a hermeneutics that always looks under the surface of what is said to see what is hidden. This would seem to make irony a problematic aspect of texts and discourse for a Gadamerian hermeneutics. Nowhere in Gadamer's corpus can we find an extensive discussion of irony, but Gadamer does raise the question of irony in a provocative way in several important junctures. This essay contrasts Gadamer's treatment of irony to that of Leo Strauss and Jacques Derrida. It explores why for Gadamer irony does not call for a hermeneutics of suspicion.