This essay examines the interplay of communication and the basic human need to integrate probabilistic and evaluative orientations. The analysis focuses on communication in four experiences where it is difficult to satisfy the need: diverging probability and evaluation (e.g., unlikely happiness or likely sorrow), ambiguity, ambivalence, and impossibility. The aims are to (a) present a rudimentary theory of communication and the problematic integration of probability and evaluation, and (b) establish the significance of the interplay of communication and problematic integration. In so doing, the essay offers a set of ideas that synthesizes and extends understandings of a wide range of communicative phenomena, from the mundane (commiserating on day-to-day concerns) to the momentous (debates about war and peace), from the idiosyncratic (coping styles) to the common (dynamics of attitude change), and from the intimate (parent-child relations) to the mass public (responding to natural disaster).