The intimate relationship between timelessness, time, and transference is generative in its clinical impact on analysis. A tendency to define and represent timelessness and time as opposing structures, antithetical in aim, can obscure the fertility and complexity of their relationship. The creative and transformative power of an (a)temporal dialectic is proposed whose engagement with transference destroys and creates new paradigms of human experience, presenting analyst and analysand with fresh ways of thinking and being. A brief history of timelessness and time in psychoanalysis follows their intertwined developmental path and their import in transference-countertransference experience.