Regarding different situations, AIs are mostly equipped with situations which are common and more readily available, so they are very good at reading news about traffic, weather, etc. But the natural tragedy is a tricky one, although it can be done since these are rare events they are not yet trained properly to handle that.
Another major challenge from the psychological perspective is the lack of empathy. When a human talks to a human, more or less there is a sense of empathy or micro-emotions which drives the conversation. These micro-emotions although are studied from decades are still far from modeled correctly in some form where AI would be able to mimic it easily.