I think that the first few times that you try to comfort someone are awkward. How many times have you felt out of place and confused when listening to someone explain their problems? I don't always know what should be said in situations like that. And when I end up saying nothing, it's almost as bad as saying something inappropriate. It's nothing like feigning interest, I actually am interested but it's just that I don't know how I should be reacting. How much sympathy should I project? Should I cry? It's not as simple as that 'do unto others' crap.