Since their creation in the latter part of the nineteenth century, women's colleges in America have undergone many significant changes. In 1960, over 230 women's colleges were in operation; over the next forty years more than 75 percent chose to admit men or shut their doors entirely (Miller-Bernal, 2006a). This chapter will shed light on the dilemmas facing women's colleges when pondering coeducation. It will look specifically to Lesley College's decision about coeducation as a case study that reveals the challenges facing many single-sex institutions. Underlying this analysis is one central question: What does the future hold for women's colleges?