When the Five of Cups appears in your reading, you are going through a transit of emotional disappointment.
The lesson from the Four of Cups is extended to this card, but it also includes an extra layer of regret and loss over a pleasure that you thought you would get a chance to experience.
The image of the Five of Cups depicts a person who is wrapped up in the black cloth of despair. Three cups lay on the ground, having spilled the wine of pleasure. He is so focused on the cups that have tipped over that he has completely missed the fact that there are two perfectly good cups of wine still available to him. But he cannot make any move toward realizing they are there, because he is too swept up in his sadness.
In life we also get swept up in what we have lost. Disappointment comes from becoming emotionally attached to something that has not come to fruition as you expected. We become extremely attached to the plans that we make in life, and when something comes through to derail those plans it is extremely difficult at points to get through. This card is referencing matters of the heart, a broken marriage or a loss of a friendship. Any kind of loss that makes you feels regret falls under the umbrella of this card. There is more for you to see, but right now it is exceptionally difficult to do so. You find that life is now no longer what you thought it would be and you are having a hard time feeling the need or want to go on. This card is one that calls out to your sadness and understands it, but the Five of Cups is telling you that there is so much more in store for you if you would only allow yourself to drink the wine of pleasure from the two remaining cups.
In some cases you have only just begun to appreciate what it is that you had now that you have lost it, and that is also a very challenging concept to take in. The process of letting go of a person or a lifestyle takes time. You cannot rush these matters. Going inward makes sense, but remember not to get stuck. True healing can occur only when you let go of the sorrow and begin to have happy and healthy interactions with others in your life who do love you.
To get out of this cycle, you must focus all of your energy on a new endeavor or project. Create some goals that you wish to accomplish but take some time to just flow. Right now it is important for you to let go of any attachment you might have to the outcomes that you have and just take one step at a time. Make a determined choice to pick up the pieces of your broken heart and move forward to your new beginning.
The Five of Cups in Love
The Five of Cups will present itself in a love reading to both honor what you are going through and to let you know what to do about it. If you are currently in a relationship that is having problems, this is going to be the card that will let you know that you must take charge of this situation and do your best to appreciate what you have or you are going to lose it. If the moment has already passed and a separation had to happen, then know that through your sorrow of this change, sometimes change is necessary for you to discover even more about yourself. As adults, we can grow apart. Sometimes we no longer want what you both wanted originally. This is a normal part of life. Spend the time grieving that you need to and then move on. In this there is some form of separation or loss that is transiting you right now, so the best thing you can do right now is hold onto the ones that do love you so that they can help you through the process of grief.
When it comes to single life in the pursuit of love, this card usually signifies a loss that is still affecting you. Perhaps you loved someone a long time ago and you find that you are unlucky in love since then. There is a portion of this loss that you have not yet recovered from, and in order for you to move forward you must. If you are in some way comparing others to that relationship, then you are not looking straight ahead, only backwards, and that is not healthy.
The Five of Cups in Health
The Five of Cups regarding health is expressing a time of your life in which you are becoming completely claustrophobic or afraid to be social. This is an extremely unhealthy place to be, as there is much that you are missing. Your physical health will be improved greatly if you start practicing getting outside here and there, meeting new people and branching out.
The Five of Cups in Work and Wealth
When the Five of Cups shows up in a reading regarding work and wealth, you can expect to be dealing with some losses. This is not the time to make investments, but to make sure that all of your legal matters are in order so that you are prepared should something relating to business change randomly.
Reversed Five of Cups in a reading
The Five of Cups will appear in a reading in the reversed position to continue to reiterate the feeling of loss that you have experienced. Think before you make any big decision. You cannot fix or change what has happened. Better to just let it go. There is a level of carelessness associated with this position as a result of the grieving period. Make sure to not abuse or mistreat others as a way to process your feelings. It is imperative now that you continue to focus on overcoming obstacles. You have only experienced the feeling of limitation, but that is not all encompassing. There is more available to you once the tears have stopped flowing.