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In our society we are frequently taught to hide our 'negative' emotions. Anger, sadness, and grief are something we are only allowed to express in the privacy of our own homes. This fosters shame around these feelings, and we begin to repress or hide them even in private. When we run into our private caves, expressing grief (or wishing it would simply go away), we miss out on a lot of what goes on around us. Our solitude and singularity in grief make us an island. This is the energy of the Five of Cups.
A man stands on the cover of the Five of Cups, shrouded in a black cloak. He covers most of his body and face with this cloak, barely revealing his eyes. His stare is focused on the ground in front of him, three cups lay dashed and spilled, the liquid they held now in puddles all around. There are, however, two more cups just behind the man... but his focus is on the spilled cups, so he cannot see the two that are behind him.
The Five of Cups can signal a loss of any kind, especially emotional. This can mean a loss of a relationship, a friend, or a lover. Of course, while this loss can indeed include death, it is more often the case of heartbreak through more conventional means. A divorce, a separation, or simply not being allowed to see that person anymore for whatever reason. Do not rule out the loss of something more physical, such as a car, job, or home – if you have a personal, emotional link to these things, then you will still feel an emotional loss at their physical loss.
The grieving process is the inevitable next step for someone who has gone through a loss, so it's no surprise that the Five of Cups represents grief as much as it does loss. Grieving has been proven to be a step-by-step process, known commonly as the Five Stages of Grief: denial/isolation, anger, bargaining, depression, and lastly acceptance. This card may be a sign that you need to accept the grieving process and begin working through these stages.
While the Five of Cups may indicate any type of loss, this card usually pertains to emotional loss. This may imply the end of a relationship, the loss of a friend, or the loss of a lover. Of course, although death may be a part of this loss, it is more frequently a case of sorrow caused by more traditional methods. A divorce, a separation, or just not being permitted to see that person for whatever reason are all possibilities. Do not dismiss the possibility of losing anything more tangible, such as a vehicle, job, or house; if you have a personal, emotional attachment to these items, you will still experience an emotional loss when they are taken away.
Lastly, this card symbolizes regret. When someone loses something important to them, you will often hear them speak of how they wish they had done something while they still had it. They will wish they had spent time with a loved one who has passed, for instance. This emotion is regret, and it stings for far longer than we think it will. This card is telling you that you might be regretting something and that it's time to try and face it and move on.
When you pull the Five of Cups in your readings, try asking yourself these questions. What have I recently lost? Am I accepting the loss? Am I still grieving? What would I do if I lost something precious to me? Would I regret anything? How can I move to prevent that regret? What step am I on in the grieving process?
Death shares several notable traits with the Five of Cups: grief, loss, and even regret. The Death card, however, indicates that new life will spring up from that loss... while the Five says that there is life already present in unseen territory. Four of Cups is remarkably similar to the Five of Cups in one way – inward focus. With the Four, the seclusion is based on denial, while the Five has the self-absorption based on grief and guilt.
When the Five of Cups shows up it is a sign that you are likely to experience some kind of upset in your life. This can range from mild annoyances to absolute tragedy but either way, it is important to embrace and process these emotions and then move on, rather than staying stuck dwelling in them or repressing them. With every disappointment, there is a chance for spiritual growth. Suffering comes from mental activity. When you learn to silence the negative chatter in your head, you can learn to be content and balanced even in the worst of circumstances. This too shall pass.