Drawn upright in a yes-or-no tarot reading, Five of Cups is traditionally a no.
Traditions differ on reversed cards. A common reading: a reversed yes softens toward "not yet", while a reversed no tends to stand firm. For Five of Cups, most readers treat the reversal as a signal to examine timing and intention before acting. Decide before drawing whether you count reversals at all.
In a yes or no reading, Five of Cups upright is traditionally a no. Loss and focusing on what is gone.
Traditions differ on reversals. A common rule: a reversed yes softens toward "not yet", while a reversed no tends to stand firm. Decide before your reading whether you count reversed cards.
One clear, answerable question — "Should I…?" — works best. Avoid double-barrelled questions; the card answers one thing at a time.