This chapter highlights key constructs and insights into gendered relationships in later life within the larger context of changing demographics and social expectations. Distinguishing later life (customarily age 65–79) from late life (age 80+) is crucial when discussing the gendered nature of personal relationships and the probability of social isolation. The chapter provides an overview of some important areas of consideration to include gendered assumptions about men’s and women’s social relationships and opportunities, grandparenting as a unique site of socialization, and sexual intimacy and connectedness. The wide-scope lenses through which older age has traditionally been viewed has lacked the finer perspectives that are important when considering intersections of race, gender, age, class, and a variety of other layers. In addition, assumptions and perspectives drawing from and relying on such large lens approaches run the serious risk of stereotyping older persons.