This paper addresses the challenges of working with narcissistically vulnerable patients who suffer vast schisms between objective and subjective time. Such patients ward off awareness of temporal limits both because they long to access an authentic sense of personal rhythm and agency, and because they cannot tolerate the encounter with past and present losses that living in real time requires. A clinical vignette centered around the developmental window of fertility illustrates how temporal enactments unfold when the analyst feels forced to choose between inviting the potentials of timelessness and the expansion of continuity and interiority, or acknowledging the urgency to act and the threat of new losses that accompany the patient’s longing to wait for subjective experiences of “readiness.”