The current set of studies examined regret involving action and inaction in the realm of romantic relationships by testing whether such regret is associated with the characteristics of one's mate. In study 1, 394 participants reported on a previous casual sexual encounter, and in study 2, 358 participants reported on a previous romantic relationship. In both, instances of actual engagement and instances of passing up opportunities were studied. Study 3 was experimental and elicited reactions to hypothetical scenarios from 201 participants. Regret reported by men in both study 1 and study 2 varied as a function of the perceived attractiveness of the participants' actual and potential mate. Regret reported by women in study 2 varied as a function of the perceived stinginess of the participant's mate and perceived wealth of the participants' potential mate. Study 3 found that sex differences in type of regret (with men regretting inaction more than women) occurred only when the mate presented in the scenario was described in ways consistent with mate preferences. Together these findings suggest that regret differs between the sexes in ways consistent with sex differences in mate preferences.