The Five of Cups is Water (connections, relationships) related to the element Ether (time, experiences, great numbers, stories, places, exploration).
The Five of Cups represents a kind of stability in connections, one achieved through strengthening of relationships over time, or alternatively one achieved through an established culture. Within this stability it is safe to have new experiences with old friends or to make new friends.
The Five of Cups may be a bar where people come to meet new friends and to reminisce with old friends. It may be a sanctuary or religious circle that offers a safe place to forge new connections. It may represent such a third place where people go to be together and have new experiences, or it may represent regularly scheduled meetings where people can go to safely explore matters, including deep, difficult or possibly troubling issues.
If it represents something private, it may be a pastime in which one can connect with oneself and find enjoyment or refuge, or comfort and safety to reflect.
The Five of Cups may also be the comfort of relationships that are stable, where trust runs deep and fosters confidence in the ability to wander the world together, or to pursue goals or try new things together.
The Abstract Five of Cups combines abstract Water (affinity, love, enchantment, allure, feeling mystified) with Ether (new experiences, the unknown, pathways). Ether oftentimes indicates many experiences or longstanding edifices, but it can also indicate novel pathways or unfamiliar situations. In this case it indicates the latter; it may signify early relationships or young love, or it may also signify being out of one's comfort zone emotionally, or being around unfamiliar people.
This card may also signify emotional immaturity or inexperience. It may be representative of tendencies that could get a person hurt or taken advantage of in relationships, or behaviors which may cause a lot of confusion and anxiety in others, like attachment issues.