Psychoanalysis promotes psychological growth by nurturing patients’ creativity and cognitive, interpersonal, and affective competence. Cultivating ironic sensibility in the analytic relationship can give rise to a therapeutic play space in which the patient’s new ways of thinking, feeling, and relating are respected and supported. In particular, irony can facilitate the patient’s growing ability to link, acknowledge, and explore previously unsymbolized, dissociated affective states. By courting irony, the analyst can assist the patient in tolerating the anxiety and shame that emerge while working through traumatic material. This article discusses both the benefits and pitfalls of irony in the analytic process.