In this chapter, the author proposes to continue his “search for meaning” in two of Woody Allen's more recent films, comparing the positions in his classic oeuvre with those in Vicky Cristina Barcelona and Cassandra's Dream. He examines whether Allen takes a consistent philosophical stance on the moral issues raised by life in a meaningless universe. The examination of Vicky Cristina Barcelona demonstrates the failure of romantic love. The author uses the existential philosophy to interpret the behavior of the characters in Vicky Cristina Barcelona. He explains Allen's pessimism about the chances for successful romantic love and his ambiguity about a reliance on emotion alone. Next, the analysis of Cassandra's Dream shows the devastating consequences of lives lived with no regard for moral values. Allen clearly believes there is no possibility of a satisfying life for those who “cross the line” and engage in grossly immoral acts.