Family-living has been recognized as a necessary prerequisite for the evolution of advanced cooperative societies, yet the evolutionary and ecological processes that drive the coupling of different forms of cooperation in family-based societies are still poorly understood. In my dissertation, I investigate the correlated evolution of parental care, monogamy, and cooperative breeding in a variety of family-based taxa. I explore the mating and social behavior of family-living beetles with incipient cooperation to better understand the factors driving these social traits. Specifically, I evaluate different causes of extra-pair mating in socially monogamous beetles, the potential benefits that young adult offspring may gain from remaining in the family group, and how these behaviors correspond to different ecological niches. These studies demonstrated that many of the factors predicted to favor family-living in cooperatively breeding animals fail to explain delayed dispersal and family cohesion in this beetle group. In a phylogenetic comparative study of birds, I further evaluate how ecological selective pressures drive the correlated evolution of monogamy, biparental cooperation, and cooperative breeding. Taken together, these studies have implications for our general understanding of the evolution of cooperation, and suggest the action of previously unrecognized processes in shaping and pairing social behaviors.