Are there limits to what it is morally okay to imagine? More particularly, is imaginatively inhabiting morally suspect perspectives something that is off-limits for truly virtuous people? In this paper, I investigate the surprisingly fraught relation between virtue and a familiar form of imaginative perspective taking I call empathy. I draw out a puzzle about the relation between empathy and virtuousness. First, I present an argument to the effect that empathy with vicious attitudes is not, in fact, something that the fully virtuous person can indulge in. At least one prominent way of thinking about the psychology of the virtuous person excludes the possibility that the virtuous could emotionally apprehend the world in a less than virtuous way, and empathizing with vicious outlooks does seem to run afoul of that restriction. Then, I develop an argument that runs in the contrary direction: virtue in fact requires empathy with vicious outlooks, at least in some situations. There is reason to think that a crucial part of being virtuous is ministering effectively to others’ needs, and there is also reason to think that other people may need to be empathized with, even if their emotional outlooks are at least minorly vicious. Finally, I outline two different solutions to this puzzle. Both solutions hold some promise, but they also bring new challenges in their train.