The paper looks into sociological implications of two discussions currently developing in behavioral economics and organizations theory: (1) regret theory, exploring the proposition that human decision making is governed by avoiding anticipated regret, rather than maximizing expected utility, and (2) studies of sunk cost fallacy, consisting in making decisions aimed at justifying previous decisions. We argue that these two areas of theorizing, presently isolated, are dealing with essentially the same phenomenon. This becomes evident if we recognize that choices are organized in sequences, with the merits of each particular choice being evaluated in the light of outcomes of the whole sequence. We then explore some general conditions of the ability to anticipate regret: interaction with one’s future Self and sequential organizations of states an individual find him/herself. We then discuss some widely spread forms of individual adaptations to the threat of experiencing regret: dissonance avoidance, prospective rationalization, cultivation of prescience, de-sequencing and open endings. We further explore various forms of collective actions involving regret avoidance, using the development of the sociological discipline as an example.