The global growth in menstrual research over the past two decades has, among other things, emphasised the role of maternal figures in preparing adolescent girls for menarche. Adult women, including mothers, grandmothers, sisters and aunts, are primarily vested in educating girl children about menstruation, guiding their adaptation to related physical, psychosocial and sociocultural developments. Despite their key role in facilitating menstrual preparation, less is known about the experiences of adult women as recipients and facilitators of these intergenerational exchanges. This paper uses storytelling and thematic analysis to reflect on women's experiences of the intergenerational exchange of menstrual knowledge. The reflections are drawn from qualitative research conducted with 20 women aged 26-52 years living in Umlazi and Inanda in KwaZulu-Natal, South Africa. The paper outlines how teachings are pathways of gendered socialisation within families. The paper also details the contradictory messaging that characterises early menstrual conversations wherein menstruation is simultaneously affirmed as normal but also stigmatised and as needing careful surveillance and concealment. Finally, the paper adds to existing menstrual discourse by highlighting the role played by grandmothers especially, in transferring menstrual knowledge, and sisters, cousins, and aunts in supporting and guiding adolescent girls' adaptation to menarche and related sociocultural prescripts.