The reversed Five of Cups represents recovery from regret and an acceptance of the past. Maybe you recognize the value of previous painful experiences that prepare you for future experiences. You are ready to pick up the remaining two cups that are full and move forth.
This card also involves learning to be open and to take risks again. Even though the card has some bittersweet sense, it is more a card of hope for the future, of getting over. If you have suffered the ending of a relationship, the reversed Five of Cups indicates the end to the suffering, and a start of relationships, new interests.
The reversed Five of Cups implies values and knowing what you really want and what makes you happy. We sometimes need certain disappointments in order to break free from illusions and find what we truly cherish. Once this transition is done, you will be completely free to take up new opportunities.