This paper critically analyzes literary representations of greensickness and menstruation in Early Modern England, utilizing cultural perspectives of medical theory and socially acceptable practices to situate these ideas and frame the inquiry. Analyzed works include a significant number of primary sources such as poems, articles, and medical books ranging from fifteenth to seventeenth century England, as well as secondary academic articles that investigated similar topics to enrich the discussion. Menstruation was less frequently treated in the literary representations, here mainly poetry, compared to greensickness. However, mentions of both were comparatively high inmedical texts from this time period, suggesting many remedies and addressing menstrual issues in great depth. Poets indicate a preference for discussing greensickness in their works, as evidenced by the generally greater frequency of works found with references to this ailment, as compared to menstruation. This paper argues that greensickness was a more socially acceptable topic to discuss, since menstruation was considered polluted and polluting, private, and taboo thus reflecting essential beliefs, values,and ideas of the time.