This dissertation investigates circumstances in which the reactive attitudes – the interpersonal and intrapersonal responses found within our distinctively human relationships – are stretched to their limits in various ways. Through an investigation of these limit cases (which nonetheless are easily recognizable in everyday life), I draw significant conclusions for our general and philosophical thinking about them. Chapter 1 explores a special kind of response to the recognition that one has nonculpably played a central role in the production of a harm. I defend the appropriateness of a specific version of this feeling, motivator-regret. Motivator-regret is appropriate when one sees one’s own role in motivating another person’s harmful action. And this response also includes a desire to address the resultant harm in some reparative way. I conclude this chapter by showing how this feeling provides the best account of the moral discomfort that many white Americans feel when considering the harmful actions of white supremacists in the country’s past. Chapter 2 shifts to the other-directed emotion of gratitude. I argue that, just as it can sometimes be appropriate to forswear fitting resentment and forgive someone, it can sometimes be appropriate to forswear fitting gratitude. Defensive ingratitude – a structural counterpart of forgiveness – is all-things-considered appropriate when gratitude would be dangerous, such as when it would make it more difficult for someone to leave a harmful relationship. To defend my claims, I provide a functional account of both gratitude and resentment, showing some key lessons we can draw from this view. Chapter 3 offers an explanation of the phenomenon of supererogation – the idea that an action might be morally good without being morally required. I argue that the best way to make sense of supererogatory actions is by seeing them as ones which an agent has strong moral reasons to do, but also would be excused for failing to do. The second half of this chapter explores excuses directly, showing a theoretically satisfying way of understanding supererogation and excuse as deeply related: two possible outcomes from the same set of circumstances.