Five of Cups does represent the challenges of the emotional processes; those that have not contemplated at the initiation but appeared on the way; predominantly the pain of letting go and the losses, because the heart does not acknowledge the concept of “for the better”; it still cries for what is no more.
The Five of Cups shows a man in a black cloak, standing in destitute. Around him; there are five cups, three of those are spilled on the ground (what seems to be blood) while the other two remains upright. Before him, a river flows powerfully; and across the river, there is a castle. To the right of the figure, however, there is a bridge; therefore the stream is not unsurmountable.
The general emotion in this card is loss and bereavement; it is most evident in the spilled cups, destitute posture and black cloak of the figure. The figure, choosing to ignore upright cups; mourns over the spilled ones. The castle represents the security the figure is yearning to reach, but again falling into the flow of the free associations of his consciousness, he fails to see the bridge that would take him there.
Character cannot be developed in ease and quiet. Only through experience of trial and suffering can the soul be strengthened, ambition inspired, and success achieved.
There is a strong feeling of loss and disappointment on this card, yet the card advises to not give up in the face of losses but to move on. The cause of the feeling of bereavement is possibly emotional. Both denying the importance of loss and letting it lead one to pessimism; however, are disillusions: One should learn from those, mourn as necessary and move on. A person represented by this card would be a pessimist, focusing on the problems rather than the solutions; almost always grieved. In a relationship reading, this card indicates that the promise and potential were not able to deliver, resulting in a feeling of disappointment; and perhaps a sense of grief at the end of the relationship. Career-wise, this card indicates an error set-back and calls for repairing and learning from it and then moving on rather than becoming sadder on it.
Summing up, the Five of Cups is a card which acknowledges that the life is no bed of roses, but even in the losses and griefs, there is an opportunity to grow.