The Five of Cups (Five of Ice in the Penguin tarot) is the card in the Minor Arcana that represents disappointment, pessimism, having plenty of regrets, as well as failure. And when this card shows up then that means you have been wallowing in self-pity and you are having a hard time getting past the disappointments that have happened.
This card shows up when you are sad and depressed over something that simply went wrong. Something that you had high hopes for but it did not end up working out and now you are indulging in your sadness over it. For instance, you may have had high hopes for getting a job that you had applied for and you did what you could to present yourself well. You created a very impressive portfolio and resume. But you did not get the job. Another applicant was chosen over you despite how well you prepared yourself for the interview and the work you put into the resume. You are feeling like a failure, you are wallowing in self-pity, and you don’t think you will ever get a job again.
It comes to a point where you need to basically allow the feelings of disappointment to run its course and move back on, and to try again.
When the Five of Cups shows up in reverse, it has two meanings. One is that you are not just depressed over something going wrong, but you are blaming yourself for it. You are dealing with a personal setback. The other is that you are finally able to move on and forgive the situation from going wrong and forgive yourself.
The associated astrological placement is Mars in Scorpio.