Psychoanalysis promotes psychological growth by nurturing patients' semiotic, interpersonal, and affective competence. Emotional, cognitive, and interpersonal maturation is often reflected through one's capacity to engage with irony within the therapeutic dialogue, as it evokes and conveys a growing ability to link, acknowledge, and play with one's multiple emotional states. Irony emerges at the crossroads of words and the nonverbal, wit and sarcasm, metaphor and paradox. Courting irony in the analytic process can assist both the analyst and the patient in tolerating ambiguity and ambivalence that arise from their internal and interpersonal worlds. The exchanges between Jamie, an adult survivor of childhood sexual abuse, and her analyst will illustrate both the benefits and pitfalls of irony and sarcasm.