The goal-directed efforts of other agents tend to strike us as to be helped, or at least, as not to be obstructed. We feel called upon in this way almost without any thought, and usually without consulting some general principle of morality, interest, or even courtesy, even where such principles may urge us along the same course. I call this general phenomenon volitional empathy, which I take to be the disposition to take what another agent wills as one’s own internal reason to will likewise—as a reason to promote, or at least not to obstruct, another agent’s goal-directed effort. This dissertation explores volitional empathy’s normative significance for regret, punishment, and trust. My first chapter seeks to show that agent regret, understood as moral self-reproach, is rationally required, even though the agent of agent regret is not morally blameworthy for the regretted event. In my second chapter, I argue that punishment, when successful, induces belated volitional empathy in the punishment subject, and thereby prompts the punishment subject’s regret for the punished violation. This effect of punishment raises the prospect that volitional empathy might underwrite interpersonal norms by giving one agent an internal reason under the control of a second agent, namely, the agent whose effort underwrites the internal reason of the first. In my third chapter, I use this idea to explain the normativity of trust: I propose that the trustor’s reliance on the trustee involves the volitional empathy of the trustee for the trustor. The trustor can enforce this reliance by compelling either the trustee’s performance, or, following betrayal, by compelling him to repair the harm he caused. In both cases, the trustor pressures the trustee with his own internal reason, which, being his own, he cannot but take as motivating. The last chapter more closely considers rebukes of the betrayal of trust. Since rebukes occur after the damage of betrayal is done, it is not obvious why they are reasonable. I show that they are reasonable by explaining how, by inducing regret, they allow the trustor to compel the trustee to repair the harm he caused.