The Five of Cups stands for loss, bereavement, and regret. For the querent, the appearance of the Five of Cups means to alert him to possibilities of a loss. It could be related to tangible loses, such as money, possession, relationship, and work; or could be intangible, such as dreams, opportunities, prospects, or reputation. The loss, the sorrow, the regret, could be great or small. When this card is drawn, the querent may already be aware of the loss; if not, this is when he must try to reduce the import of the loss, if not avoid it altogether.
The querent needs not be discouraged by the appearance of this card, as every negative has a positive side to it. The figure on the Five of Cups card is draped in black, and covered in grief. He is staring at the upturned Cups in front of him, oblivious of the fact that there are two upstanding Cups behind him.
Loss always hurts, as we always resist change. However, every loss opens up new opportunities and possibilities for growth. Every loss initiates a change. We need to go with the flow. If we struggle to hold on to what is gone, we suffer more.