The Five of Cups represents loss, bereavement, and regret, but it also shows that there is still hope. Two cups are still standing, and they encourage the seeker to stop wallowing in self-pity and let go of the past.
Brynjolf and Karliah stood by the font in the Twilight Sepulcher, preparing to summon their Lady Nocturnal. They had already known about the sun’s disappearance before receiving Selene’s letter, but until now, they hadn’t acted on what they had learned. Even after hearing from Selene, Brynjolf was skittish about summoning the Daedric Prince, preferring not to draw attention to himself and the others. He had made his commitment and would honor it, but the thought of lingering as a ghost in the Sepulcher until Nocturnal decided he had fulfilled his contract scared him. There was no set amount of time, just Nocturnal’s whim. What if, when they called on her, she decided to extend the contract as payment for her inconvenience? What if she never let him out of his contract? He would just float around the Sepulcher for all eternity. And if she did end it, what then? He would become nothing more than a shadow. Would he be conscious? Would he know what was happening to him? And would he care?