Pregnancy and childbirth typically are associated with positive emotions and with motherhood, but the reality is that this is not the case for all women or for all pregnancies. This review addresses a different aspect of these reproductive events, focusing on stressful circumstances surrounding pregnancy, as well as times when the pregnancy itself becomes a stressful life event. Pregnancy-related topics that tend to receive less attention will be emphasized. These include issues related to infertility; unplanned pregnancy; stress associated with testing and diagnosis of common medical complications; peripartum cardiomyopathy; fear of childbirth; and pregnancy loss as a risk factor for psychopathology. Epidemiologic information will be presented, as will relevant psychosocial factors related to each phenomenon. Healthcare providers should be sensitive to the distress and anxiety experienced by many women and their families as a consequence of these adverse events and the stressful challenge of any consequential decision-making, as well as stressors in their broader life context that can further exacerbate their distress, and make mental health referrals as appropriate.