This is what Biddy Tarot has to say about the five of cups, and so does Rider-Waite. This is generally the card I select for a tarot reading from a professional:
The Five of Cups represents a lack of fulfilment or non-attainment of expected results. You are feeling disappointed that a situation has not turned out as you had hoped, and instead of moving on to greener pastures, you are wallowing in self-pity and regret about what has been lost. The water spilled from the cups shows that the cause for regret is more emotional than financial. You are quickly becoming disillusioned with life and increasingly pessimistic about your future.
The Five of Cups suggests that you are having trouble letting go of the past and learning from your mistakes. This card can often reflect a person who is caught up in the past and unable to move on, missing out on new opportunities. Bitter memories from the past continue to bother you, and often a great deal of the blame for past actions is placed on yourself and your inadequacies. To some it would seem that there is no way out of this situation but the Tarot always shows problems on one hand and solutions on the other.
Forgiveness and the ability to recover after emotional loss are necessary. If you are feeling disappointed by another person’s actions, and then find it within your heart to forgive that person, releasing yourself from the disappointment. You may also need to re-assess your expectations that have led you to this disappointment. Were you expecting too much?
Remember, too, that hindsight is much clearer than foresight and present-day wisdom is gained from the mistakes of the past. Reflect on what lead you to this point and understand what important lessons you can take from the experience. Even when things go pear-shaped, there is always something positive that can be gained by reflecting on the lessons learned.
While it is true that much has been lost, there is still a ray of hope because some of the cups in this card remain full and upright. You must not pity yourself when you find yourself in his situation. Instead of looking at the situation from a ‘glass is half empty’ perspective, look at it from a ‘glass is half full’ perspective. If you can stop your sulking or even crying for a moment, you can open your eyes and see the way out of this disappointing situation. You will have to work on it but it is there.
The Five of Cups also tells you to be thankful for what is left. Do not worry about what cannot be changed. Instead, focus on turning a setback into a step forward. Never let your tears stop you from seeing what is left over.
This is gratifying advice. I have been stuck in a place I'll call 'purgatory' for lack of a better word. I put myself there, and I kept myself there. I was always going over something that had happened in the past and wishing I had done something differently or reacted differently.
No more! This Five of Cups is moving on. I am going to choose a new card to represent myself, and hopefully that will change what I project into the world. Now you must ask yourself, "Am I a Five of Cups?" If the answer is yes, please join me and move on!