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Philosopher Paddy McQueen provides a detailed examination of the nature of regret and its role in decision-making. Contrary to influential philosophical accounts of regret, he argues that we should only regret choices we make that were not justified at the time, based on the information that was available to us. Consequently, he suggests that many of us should have fewer regrets than we do, and we should worry less than we do about whether we might come to regret a decision. In making this case, he engages with important areas of philosophical debate, such as reasons, time and justification, the temporal self, values and valuing, responsibility, the causal framing of events, and self-forgiveness. The result is a complex, novel account of when we should regret the things that we do. In addition, McQueen explores how experiences of regret are shaped by social discourses, especially those about gender and parenthood. He examines how regret has become politicized in debates about abortion and trans identities and reveals ways in which regret is used to regulate people's reproductive choices. Through this cultural politics of regret, he challenges assumptions about gender identities and the expectations of regret that are attached to certain people's decisions. In so doing, he shows how confronting these assumptions and expectations can help to promote people's autonomy and well-being. Weaving these threads together, McQueen highlights the personal and political significance of regret.