This is the obstetrician’s view on 3 different clinical scenarios involving bleeding and thrombotic disorders. In the first scenario, an 18 year old with a history of heavy menstrual bleeding since menarche presents with abdominal pain and ultrasound findings suggestive of a hemorrhagic ovarian cyst. The association with an underlying bleeding disorder is recognized. The goals of management, which are controlling hemorrhage and preserving fertility, are stated. Ovarian suppression, the most effective method to prevent recurrent hemorrhagic ovarian cysts, is outlined. Long-term management of heavy menstrual bleeding with hormonal contraception is described. In the second scenario, the same patient returns 5 years later for a preconception visit. The potential risks to an unborn baby with von Willebrand disease (VWD) are addressed. The natural rise in von Willebrand factor (VWF) during pregnancy is discussed, but the fact that women with VWD do not achieve the same VWF levels as women without VWD is emphasized and the implications are presented. In anticipation of pregnancy, the need for nonhormonal management of heavy menstrual bleeding and hemorrhagic ovarian cysts is mentioned. In the third and final scenario, the patient’s cousin with factor V Leiden seeks consultation regarding the risks of thrombosis with in vitro fertilization. The steps of assisted reproductive technology are described. The strategies to prevent venous thromboembolism by preventing ovarian hyperstimulation and reducing the likelihood of multiple gestation are detailed.