General

The Five of Cups symbolise regret and sadness, and is often a break up card. The Five of Cups is about loss and the challenges that stem from this loss. When I see the Five of Cups, this is often an indication that someone is wallowing in self pity and sadness, so much so that they do not notice the blessings and the good thing that is before them. This is because in traditional tarot, there is a figure in black with his back turned. In front of this person are three cups that have been spilled, and behind are two cups that are still full. This person is too busy mourning the three cups to notice the ones that are full. Hence, this is why I often associate this card as a self pity card.

Upright

The Five of Cups is a card of disappointment and a card that predicts that things may not turn out the way you expect it to. Sometimes this can indicate someone who is unwilling to let go of the past and see the blessings that are there in front of them. In love, this is a break up card and it’s a card that talks about the grief that follows the breakup. This indicates that the breakup is still fresh, and it is unlikely that there would be any reconciliation or peaceful resolution anytime soon. In career and finances, this could mean a job loss or financial loss. Perhaps this could mean a demotion in your job. The Five of Cups is just not a great card to receive for anything as it talks about challenges and difficult times.

Reversed

In the reversed position, the Five of Cups is a slightly more positive card, and it symbolises recovery and acceptance. This is a card that indicates that you are on the path to moving on. In love, this could mean that you are moving on from the past and healing the past. And now are ready to embrace the new, and ready for a new beginning in love again. Whether this means that there would be a reconciliation really depends on the surrounding cards. In career and finances, the loss of your job could be a blessing in disguise and it may lead to better positions. This could also mean that there is healing from the job or financial loss.