This paper explores the complex interplay that unfolded between analyst and patient around their respective childlessness and aims to draw attention to the larger societal issues of imperative parenthood and the stigma of childlessness. As the analyst confronted her own internal conflicts about motherhood, children, and procreation as a woman living in a pronatalist society (one that encourages increasing birth-rates), she was treating a lesbian patient with a history of childhood relational trauma and sexual abuse who was undergoing fertility treatments. The patient’s experience with assisted reproductive technologies raised complicated questions and concerns within the analyst regarding their emotional impact on her patient and, more broadly, how they might reflect societal dissociation. Themes of trauma, loss, dissociation, and shifting self-states, which emerged during the fertility treatments and wove their way throughout the analysis, are discussed. In addition, the author describes the nature of the therapeutic action in this case.