Dregs of Sorrow and Cups of Hope
The Five of Cups depicts a figure cloaked in black, standing amidst two full cups, and three overturned ones. The figure looks dejected, and seems unsure of where to go and what to do next.
I think of this card as representing depression and uncertainty. Like all of the fives, it is a harbinger of change or transition. My pip card cheat sheet has it as “crying over spilled milk.”
Life is change, and uncertainty. Some of that change is unpleasant and sorrowful. The challenge that this card poses is to face whatever comes without being drawn into negative states of mind.
Take up the hopeful cup.