In representational art when people are portrayed, it is impossible for the artist to be objective. If what you are looking at in a painting is derived from the real world and not an abstraction from the artist's mind, then as the viewer, you will project your own imagination and perceptions on to the work.
I am fascinated by the representational work of Jorge Santos whose photorealist style places people in often surreal environments and begs the viewer to ask..."what the hell is going on?" His paintings are often humorous and ominous. Similar to reading a good book or watching a movie, the viewer's psychology will play a key role in either the enjoyment or discomfort of the art.