The Five of Cups is a profound, powerful, yet subtle card. In a reading, it usually refers to a loss we have suffered: something we valued or hoped for us has ended in disappointment, represented by the three spilled Cups. It is only for us to know - or intuit - whether those lost Cups contained what we hoped they did. Either way, the pain right now is deep, and may, in some cases, be tinged with regret, if we feel we have played some part in what has happened.
The Five, despite initial appearances, is a card of hope. When the woman is ready and has accepted what has happened, then she will turn, realizing (or remembering) that two standing Cups remain behind her. The bridge spanning the river in the background of the card represents the road back to life again, waiting for us to cross, and the building beyond it symbolizes stability.
Two meanings present themselves when the Five of Cups reversed comes up in a reading, and the other cards in the spread, and our intuition, will guide us as to which is the correct one. Firstly, the reversed card can indicate that we are not accepting the loss that has come about; as a result, we may be prone to making unwise decisions, or choices that do not serve us well. In this scenario, the card counsels that we may need a time of introspection so that we can fully recognize what has happened. Secondly, the Five of Cups reversed can indicate that we are ready to turn to what remains with a sense of deep appreciation.
The Five of Cups is both a card of loss and of hope: the standing Cups may still be upright for the simple reason that they are not so easily knocked down - which suggests that, perhaps, the spilling of the Three that were easily toppled is not a loss of the magnitude that we had originally thought.