"It's no use crying over spilled milk"
Tarot imagery for this card is, in general, one of a sad figure lamenting over turned, empty, cups. The loss of water symbolising emotional loss. In the Rider Waite Smith deck the person stands head bowed, facing left, with 3 over turned cups also on the left. It's important to take note of the direction a character is facing when looking at symbolic imagery. The left represents the past. These over turned cups are a past event and they are mourned by someone lost in that past. We can't see the face and this character wears a cloak. They have shut themselves off from others. Behind them remain 2 full cups, on the right, in the future.
In Numerology the negative aspects of the number 3 are loss, bad luck, heart ache. (See the 3 of Swords). If you look through the suit of Cups you'll find one other card with two full cups. The 2 of Cups. In such a negative card these two full cups point to a brighter future. Something new to look forward to. The message here is to let the past go, accept what is and move on and embrace new, emotional, possibilities and partnerships.
The 5 of Cups is a card of emotional loss, regret, melancholy, self pity or feeling blue. The element here is Water which relates to love and emotions. In numerology the number 5's positive traits are change, unattachment, adaptability, freedom. The negative traits are instability, irresponsibility, carelessness, thoughtlessness and over indulgence.
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THE PICTORIAL KEY TO THE TAROT
By Arthur Edward Waite (1911)
A dark, cloaked figure, looking sideways at three prone cups two others stand upright behind him; a bridge is in the background, leading to a small keep or holding. Divanatory Meanings: It is a card of loss, but something remains over; three have been taken, but two are left; it is a card of inheritance, patrimony, transmission, but not corresponding to expectations; with some interpreters it is a card of marriage, but not without bitterness or frustration. Reversed: News, alliances, affinity, consanguinity, ancestry, return, false projects.