This chapter provides an overview of the etiology, symptoms, evaluation, and management of abnormal uterine bleeding (AUB), amenorrhea, premenstrual syndrome, menstrual headaches, and dysmenorrhea. In order to address abnormal perimenstrual conditions, it is important to first understand the normal menstrual physiology. Pregnancy is the primary reason for AUB. Health care providers should consider gynecologic structural defects or systemic sources as possible causes of AUB, once pregnancy has been ruled out. Ovarian dysfunction is typically the source of AUB at the extremes of childbearing age groups. Imperforate hymen and a transverse vaginal septum may obstruct menstrual flow, yet women may experience cyclic premenstrual changes and complain of pelvic pain. Anovulatory menstrual patterns are sporadic in timing and volume and can be related to hormonal contraceptive use, pregnancy, and pelvic infection. In some instances, diagnostic imaging may be indicated to rule out pelvic abnormalities and definitively diagnose primary dysmenorrhea.