The modern increase in opportunities for social activities also brings with it unintended side effects posed by the liberating potential and the acceleration of modern life. In this paper it is argued that the views reflected in Georg Simmel’s formal approach and in American sociologist Edward A. Ross’ reformative sociology are (1) complementary and (2) offer fresh insights for our current sociological understanding of unexpected consequences in contemporary “high modernity” or knowledge societies. A long forgotten nexus between the ideas of Simmel’s and the work of Ross will be reviewed in order to point out affinities between the two authors’ takes on the unintended and sometimes tragic moments in modern culture and their relevance for sociology today. Based on these discussions a fundamental mode for framing the unexpected in modern society as a recursively-linked component to the intended is illustrated.