Multiple pregnancies occur in humans and other primates, which indicate that the twinning propensity is phylogenetically old. Factors such as decreased sexual dimorphism and size, rich and diverse nutrition and paternal care are related to multiple pregnancies in other animals. In human populations, despite its costs, twinning has a genetic basis and in Europe, Africa, and America, it was found that it increases mothers' fitness. Here, we explore the hypothesis that twinning represents an evolved physiological mechanism, particularly in mothers of higher age, as an 'all-or-nothing' last chance strategy for reproduction just before menopause. We present decade-long, large-scale population data about maternities from the city of São Paulo and the entire country of Brazil that indicate a considerable main effect of advanced age in promoting twinning, particularly dizygotic (DZ) twinning, but also monozygotic (MZ) twinning and higher order maternities. We also show that socioeconomic status is an important contextual factor increasing twinning. Besides the theoretical implications, these datasets establish a Brazilian countrywide twinning rate of 9.39‰ and highlight an increasing historical trend. This chapter promotes the importance of integrating proximate patterns from human and nonhuman animals and evolutionary factors in order to reach a comprehensive view about twinning.