Five of Cups Emotions associated with Five of Cups are: Regret, failure, disappointment, pessimism, personal setbacks, self-forgiveness and moving on. In the “Five of Cups” card, we can see a man who has worn a long black cloak. He is looking down at the three cups that have fallen. These three fallen cups represent disappointments, … Continue reading Five of Cups : Its 1 Of The Most Powerful Cards.