Meanings according to Rider Waite:
ASTROLOGICAL SIGNIFICANCE: Saturn/Venus or Saturn/Moon as a symbol of separation, pain, grief, and despair.
FIVE OF CUPS The Five of Cups is a card of sorrow, pain, despair, and melancholy. It indicates that we have lost something that was very important to us for a long time. It shows that we will not be left alone with our grief, but can count on the sympathy and help of friends. However, this consoling aspect of the card should not be interpreted to mean that our grief is imagined and that we will soon be happy and cheerful again. Often the card reveals that our own carelessness was to blame, that we did not value what we had, and therefore lost it. Yet there is a way out of this situation as well: the card advises us not to dwell on our grief for too long.
From the book: Hajo Banzhaf. THE TAROT HANDBOOK. Translated from German by E. Kolesov. Publisher: Center for Astrological Research, 1999.
FIVE OF CUPS Disappointment First decan of Scorpio from October 24 to November 1. Astrological equivalents: Leo, Cancer, Saturn. The sign of Scorpio symbolizes the development of feelings in depth. The first decan of Scorpio expresses the idea of a passionate and demanding analysis of life and the search for its essence. This decan is ruled by the planet of hidden potential, passion, and suffering — Pluto (Mars in the old system). This decan is characterized by emotional dissatisfaction, inner uncompromisingness, and the desire to remake the world. It is self-sacrifice, contemplation of death, and the need to renew life again and again. This card signifies some kind of strong emotion, perhaps righteous anger or a wild romantic infatuation. At the same time, the card has a Saturnian-Uranian flavor — there is, as it were, a purification of emotion, a testing of its truth. On the TAROT card, a man in a black-and-red cloak has covered his face with his hands: his figure expresses sorrow. He stands before three overturned CUPS, not knowing that behind him stand two full ones. He grieves for the feelings by which he formerly lived and in which he became disillusioned, having learned the truth he had sought to know. He thinks that the goal of his existence is lost — but in reality he is grieving only for the past, standing with his back to those wellsprings of life that nourish his present. He need only turn to face them — and his former tirelessness, thirst for the ideal, steadfastness, and readiness for action will return to him. He will understand that his emotional efforts were not in vain and led, above all, to the renewal of his own life. Something has flowed out, drained away, and the sky has darkened. What once filled you to overflowing has now run dry. Pain, loss, disappointment. This is not a cosmetic adjustment; it is a radical disillusionment. There is nothing positive here. At the same time, the card points to the (false) point of view we often adopt in such a situation: the gaze is directed to the past. We are not yet able to see what will reward us for our disappointment. Emptiness can clear a space for new replenishment. Sometimes this card means liberation from delusions. The FIVE OF CUPS is maximalist, sometimes even excessively so. On the emotional level it tends toward the "Gothic" — that is, cutting off everything superfluous, to feelings on the "all or nothing" level. Here a very strong influence of Saturn makes itself felt, bringing into the action of the card something of the implacability and uncompromisingness of Capricorn. On a low level, the FIVE OF CUPS is realized precisely through Saturn, bringing with it losses, disappointment, sorrows, and a sense of imperfection. It is precisely here that all shortcomings in the building of relationships, all things left unsaid, may "surface." At the same time, like every FIVE, the FIVE OF CUPS symbolizes an attempt to break beyond the rigid quaternary form. Within the suit of CUPS this breaking-out occurs through connection to a great current, a great tradition. Venus (the principal planet of CUPS) hinders direct confrontation. Therefore the card may indicate strengthening through tradition, through the past, which is realized through one or another form of spiritual inheritance, the recovery of forgotten knowledge. On a low level this may indicate a gift or inheritance in the most literal and direct sense. Higher — at the level of the card — Leo already sounds. The trap is to dwell in one's sorrow. He who looks only backward will not notice love, even if it is right beside him.
UPRIGHT POSITION In the upright position of the card it would be more correct to say that the influences of Leo and Cancer are mingled in this card. At one pole, metamorphosis in love relationships, even sudden changes; at the other — typically "Cancerian" manifestations, such as ancestors, gifts, inheritance. (Both Cancer and Leo, in one way or another, draw attention to the past.) In love — these are past unspoken matters that now become obstacles; in affairs — these are all manner of past oversights. The traditional meaning of the FIVE OF CUPS is disappointment, tears and regrets, sorrow, the loss of the source of feelings, radical sudden and painful realization. Abortion.
REVERSED POSITION In the reversed position the card signifies: a new outlook on life, hope, encouraging news, pleasant experiences, new alliances, connections, the return to old friends, reunion, the return of the "Lion who has roamed his fill."