Three experiments were conducted investigating feelings of regret following poor decisions involving behaviors that were either typical for the decision-maker or atypical. Using a retrospection paradigm, the present research found that typical behaviors were more regrettable when decisions were in the context of goals to change whereas atypical behaviors were more regrettable in the context of maintenance goals. We ruled out explanations of these effects based on the temporal distance of the decision, behavioral typicality per se, the severity of the decision-outcomes and the ease of recalling the events. Results were discussed from a consistency-fit analysis of regret and decision-making.