The purpose of this chapter is to review three menstrual cycle-related health concerns: Polycystic ovary syndrome, dysmenorrhea, and menstrual migraine. Each is characterized by symptoms temporally associated with the menstrual cycle and related endocrine fluctuations. Each is reviewed from a biomedical perspective (including diagnostic criteria and usual therapies) and then contrasted with women’s reports of their experiences. Little attention has been paid to the ways in which women’s culturally-determined gender role interplays with the etiology of the conditions, willingness or ability of women to seek help, and response of medical professionals when women do seek help. Investigators appear to assume that all study participants were cisgender individuals with both biological structures and hormones typically identified as female as well as a female gender identity. Future researchers need to parse out the effects of female physiology from feminine gender role and female identity.