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Puberty marks a developmental period of profound physical, hormonal, and psychological change. This paper explores some of the brain transformations that occur during puberty and considers how they may mirror – and possibly enable – the psychological task of separation and individuation. Focusing on female psychosexual development, the paper examines how menarche (first menstruation) and the menstrual cycle signal a fundamental shift from pre-pubertal linearity to a cyclical way of being. It argues that the menstrual cycle has been largely neglected in psychoanalytic thinking. Prominent early psychoanalytic formulations of female development, alongside representations of menarche and menstruation in theory and literature, are reviewed. The paper also situates menarche and menstruation within broader Western cultural history. Attention is drawn to the silence surrounding menstruation – not only in psychoanalytic literature but also in clinical work with adolescent girls, where discussion of the menstrual cycle often remains difficult. In response, the paper introduces an innovative, psychoanalytically informed workshop developed by the author for mothers and daughters, designed to foster menstrual cycle awareness and thoughtful preparation for menarche. Finally, it invites psychoanalytic psychotherapists to reflect on what it means to live in a cyclical body – both as therapist and patient – and to consider how different phases of the menstrual cycle may shape cognition, affect, and behaviour. The paper calls for a more open, nuanced integration of these experiences into therapeutic work with adolescent girls.