Regret is a negative emotion that we generally experience after acting in ways contrary to our normative standards. Many scholars argue that this emotion has little, if any, practical or moral justification. As a result, it is on-balance unwarranted. Some scholars argue that regret is simply adding an additional pain to the first pain (when the regretful action was made) and is therefore impractical and unreasonable (Bittner 1992). Others argue that most of the regret we experience is inappropriate. If we regret what happens in the past from our current psychological and normative framework, it is inappropriate because we are no longer the same person, in the relevant way, who transgressed (McQueen 2017). However, little research has directly addressed the normative and practical justification of regret from the standpoint of one’s current value system. My project considers how regret should be viewed and why it is valuable. It also reorients the literature toward a more straightforward understanding of regret and regretting that most people appear to experience. In Chapter 1, I consider the regret skeptic and the common objections to regret. In Chapter 2, I consider how regret has been misunderstood and seek to consolidate a coherent and consistent definition. In Chapter 3, I defend regret on the grounds that there is value in acknowledging the regretful act because of the way it activates and reorients us to what we value. I also show that there is value in learning from regret. This not only applies to making better choices in the future but also to improving our character as a result. In Chapter 4, I defend the view that being able to display regret is a social commodity because of its regulative and symbolic functions. The regulative and symbolic effects of regret are useful in our social and legal practices. It is only when we are in a position to consider the normative and practical benefits of regret that we are able to consider whether or not it is worth the pain