Upright the Five of Cups is read as grief, regret and disappointment fixed on what has been lost; reversed, as acceptance, forgiveness, and the turn toward what still remains.
Cartomancers working the suit before Smith's picture existed read a bare five of cups, like any suit's five, as disruption breaking a settled four, an unhappiness in matters of the heart without her specific staging of two cups left unseen; it is the picture, not the older number-based tradition or the Golden Dawn's Mars-in-Scorpio placement, that supplies the reminder built into the card that something remains, since neither the bare number nor the occult title requires any hopeful remainder at all.
Waite's own printed meaning for the reversed card, a return, a renewal, an alliance restored after a quarrel, is somewhat more concrete and relational than the general acceptance most contemporary readers now describe, another instance of the deck's twentieth-century drift toward reading feeling states rather than events.
Because the figure's back is turned rather than his eyes closed, careful readers commonly treat the card less as a claim that recovery is impossible than as a description of where attention currently sits, which makes the reversed meaning read less as an external rescue than as the same figure finally choosing to turn around.