When people are making certain medical decisions – especially potentially transformative ones – the specter of regret may color their choices. In this paper, I ask: can predicting that we will regret a decision in the future serve any justificatory role in our present decision-making? And if so, what role? While there are many pitfalls to such reasoning, I ultimately conclude that considering future retrospective emotions like regret in our decisionmaking can be both rational and authentic. Rather than indicating that one is about to make a mistake or that there is some underlying value that one already cares about but is overlooking, the prediction that one will regret a decision in the future makes one confront how her present values and ...