If imaginative sympathy is only one way of approaching character, it also has some more general limitations. The phrase ‘the creative imagination’ is one which almost everyone on the planet seems to find unequivocally positive, like ‘We’re off to Marrakesh tomorrow’ or ‘Have another Guinness.’ But the imagination is by no means unambiguously positive. Serial killing requires a fair amount of imagination. The imagination is able to project all kinds of dark, diseased scenarios as well as a great many affirmative ones. Every lethal weapon ever invented was the result of an act of imagination. The imagination is thought to be among the noblest of human faculties, but it is also unnervingly akin to fantasy, which is generally ranked among the lowest.
In any case, trying to feel what you are feeling will not necessarily improve my moral character. A sadist likes to know what his victim is feeling. Someone may need to know how are you feeling in order to exploit you more effectively. The Nazis did not kill Jews because they could not identify with what they were feeling. They did not care what they were feeling. I cannot experience the pains of childbirth, but this does not mean that I am callously indifferent to someone who does. Morality has precious little to do with feeling in any case. The fact that you feel a surge of nausea at the sight of someone with half their head shot away is neither here nor there as long as you try to help them. Conversely, feeling intense compassion for someone who has just fallen down a manhole, while nipping down a side-street to avoid having to haul him out, will not win you many humanitarian prizes.
– How to Read Literature (Yale University Press)