Given the pivotal role of differential reproduction to the evolutionary success of ancestral men, evolution has produced a plethora of reproductive strategies aimed at solving the complexities of intramale competition and satisfying and/or thwarting the reproductive desires of women. Life history theory recognizes that an organism has limited resources and must invest energy appropriately. Broadly, reproductive strategies can be dichotomized into short-term (emphasizing mating over parental effort) versus long-term (emphasizing parenting over mating effort) strategies. Increasingly, the neuroendocrine system—especially testosterone—has been recognized as the proximate mechanism orchestrating adoption of one strategy over the other. This chapter reviews behaviors geared toward solving problems associated with both long-term and short-term reproductive strategies and discusses the neuroendocrine correlates. The adoption of one strategy over another is conceptualized as conditional or facultative adaptations in which strategic switching points are tuned over evolutionary time to produce optimal fitness responses to men’s social and physical conditions.