This study reads Auden's poetry and plays through the shifts from modernism to postmodernism. It analyzes the experiments in Auden's writings for their engagement with crucial contemporary problems: that of the individual in relation to others, loved ones, community, society, but also transcendental truths. It shows that rather than providing firm answers, Auden's poetry emphasized the absence of certainties. Yet far from becoming nihilistic, it generates hope, affection, and most importantly an ethical challenge of responsibility of its discoveries.