I have been doing some thinking about the five of cups and been doing some math. In it there are three spilled cups that a morose cloaked figure seems to be ruminating on, with two upright cups behind them.
What comes to mind for me is the two separate cards of the three of cups, (where we see three feminine energies holding up three cups in celebration of their bond.), and the two of cups. However, since the three cups in the five of cups is upturned and spilled it would point ruminating on the shadow aspect of the three of cups. All cards have a shadow aspect as well as a light aspect. The shadow aspect would definitely related to reversals and in this case overturned cups.
The shadow/reversal aspects of the three of cups would be, gossip, scandal, excess, isolation, loneliness, solitude, imbalanced social life. This seems to be a flow on effect and seems to be from a self-consciousness within their own relationships. The gossip and scandal part forcing someone to view their relationships from the outside and disrupt their own presence in their own life. Effectively making them a spectator within their own life, the opposite of main character energy. This is someone who defers to someone else's say so about their lives. Who either has a lack of boundaries or a lack of ability to identify and express their boundaries.
By the time it's the 8 of cups, the gossip and scandal has happened two times over and the person, fed up, is walking away. Leaving 8 cups intentionally been cleaned, turned upright, and waiting for the waters of emotion to fill it. This is someone who has considered what they want out of a relationship and what their boundaries are. This person does not need closure to have decided to leave a toxic situation. A person's actions is enough closure for them to detach if their actions do not meet their standards. This involves a lot of self-knowledge and self-awareness.
The 9 of cups, this person has found something or someone that brings them joy, the ace of cups with the 8 of cups. Their cup runneth over enough to be able to give to themselves and others. It's a card of thriving, self-sufficiency, mastery of self, and being ready for a healthy relationship once they feel whole within themselves.