The movie begins with a story told by the father of the main character in the story. There once was a young prince, seeking to please the king of the East, who was his father. He ventured on a journey to Egypt, seeking a majestic and valuable pearl. On his way there, he met some people that offered him a drink from a cup. Drinking, he forgot his mission, his father and his purpose. The King, his father, sent messengers to lead him back home.
Rick, who has now grown up, is searching for a meaning to his life. His father, who is now deep in guilt for another of his son’s death, used to tell him the story of the Knight of Cups when he was younger. Wandering around, searching for purpose, he works as a screenwriter, hoping to give with viewers something to hope for as well.
The movie is then turned into chapters, each focusing on a woman Rick spent time with, which he ultimately left or broke up with. However, they all taught him something new and strengthening about himself. Della, Nancy, Helen, Elizabeth, Karen and Isabel are all wise women and have somehow learnt what life is about. They are his guide, his messengers leading him to the East, leading him back home.