The current study examined how event saliency and reason for action influence the amount of regret anticipated about a foregone option, and on people‟s anticipated choice of behavior when they are confronted with a choice between two equally aversive options. The participants were 120 undergraduate psychology students. Participants who were prompted to imagine choosing to fulfill an internal desire instead of an internal obligation anticipated significantly more regret than those who were prompted to make the opposite choice. No significant differences in the amount of regret anticipated was found between participants who had to choose between two external obligations. Interestingly, participants were not more likely to choose an action which would have avoided a salient outcome, when imagining actually being in the situation. These findings were interpreted to suggest dissociation between people‟s anticipated emotions and subsequent choice of action regarding important preventative health behavior. The implications for health promotion campaigns are discussed.