The Five of Cups represents grief, loss, and a depressed mood. This card oftentimes makes an appearance when there has been a broken romance or friendship of some kind.
Historically the card represented inheritances following a death which also ties into this cup's principal meaning of an emotional loss.
In the Rider Waite deck a lone character swathed in the mourning colour of black cuts a lugubrious figure.
He is flanked by three cups to his left which have fallen and two to his right which remain vertical. His gaze, however, remains firmly fixed on the cups which have fallen, symbolising that whatever is plaguing him is something that he is not easily able to overcome. Although hope and promise is represented by the two cups still standing, this individual is not yet able to see the bright side of his predicament.
In a love reading this card is one of the chief cards which represents a separation. It predicts a divorce, separation and an almost insurmountable hurdle to overcome within your relationship. However, since this card formerly represented inheritances, there will be a silver lining to your situation which may come in the form of being able to move on to better things.
If a separation is not likely, this card can show that either you or your partner are trapped in a pessimistic way of thinking and that such thinking is doing nothing to improve matters between you. If this is the case, professional help is advised. If your connection is relatively new, this card can reveal that you are dealing with a chronically melancholic character who is far too consumed with their own emotional issues to pay you much attention.
In a work reading the Five of Cups symbolises abandoned plans and fractured working relationships with your colleagues. In this context, the Five of Cups can also indicate an individual who allows their mood to dictate their performance too much, which can cause the best laid plans to go awry. Lastly, it may reflect that you are dissatisfied with your current role which in turn is causing you to feel no end of discontent: in this instance it may be wise to search for better opportunities.
Positive Aspects: inheritances, silver lining, letting go of a bad situation to welcome better things
Negative Aspects: grief, loss, death, depression, preoccupation with oneself