Five of Cups Tarot Meaning: Upright and Reversed

What does the Five of Cups tarot card mean upright and reversed? We explore its symbolism, interpretation in love and career, and what it reveals about feelings, advice, and yes-or-no answers. 

Five of Cups Keywords Upright and Reversed 

• Upright: Regret, disappointment, loss, separation, and feeling pessimistic. A sense of despair; lack of ability to see opportunities that are there. 
• Reversed: Acceptance, acknowledgement, moving on, forgiving, and letting go. 

Upright Five of Cups Description and Symbolism 

This is one of the least fortunate tarot cards, and it does signify a period of difficulty in life: the challenges of dealing with loss, mourning a situation that has ceased to be, and beginning to pick up the pieces and move on. Now depicted on this card is a figure who wears a black coat, he is hiding his face; there is a sense of despair, and he is downcast. His body language is vulnerable and defeatist.

The picture shows five cups in front of him which have fallen and spilled onto the ground, and there are another two behind his back which are still standing. Importantly, he fails to notice the upright cups because he is so focused on the fallen cups. Ahead of him there is a river flowing between himself and a castle in the distance. To his right is a bridge, which can potentially help him get across the river to the security of the castle. So, despite this card indicating trials and tribulations or a transition period, there is a positive aspect as well, represented by the bridge, the castle in the distance, and the two upright cups. 

Upright Five of Cups Meaning 

Seeing this tarot card can represent a time in your life when you are suffering disappointment. Perhaps a job or relationship hasn’t panned out as you expected, and you’re having to cope with a sense of disappointment, loss, or even despair. The card indicates that you’re not quite ready to move on as you are still going through the process of anger, bargaining, grief, and eventually acceptance over what has been lost. The water that has spilled from the cups shows the loss will be more emotional than financial ie it may be a broken attachment or loss of a significant person in your life who has perhaps moved or moved on, but this doesn’t necessarily mean bad luck financially. 

This tarot card shows that, in the interim, you are pessimistic about your future, but there are many positives which you will start to uncover as you go through the grieving process. This card encourages a phase of acceptance and then letting go, so you do not become caught up in the past and unable to move on. It does indicate that you are currently not seeing the benefits that can come out of the situation, because there are many powerful opportunities indicated. 

It’s vital not to get caught up in bitterness, resentment, or the blame game. Forgiving both yourself and others for what has transpired is an important part of the grieving and acceptance process. 

Love Meaning Upright Five of Cups 

This could suggest a recent relationship breakup or a disappointment. It’s likely that someone you met was promising at the start, but perhaps the relationship fizzled out, or they turned out not to be the person you thought they were. In some cases, you may end up not being interested in pursuing the relationship. So, whether it is yourself or the other person who breaks it off, there’s still a sense of disappointment at the lost opportunity. 

This card represents that you were once happy and hopeful about a situation, but it has ended up not realising your expectations. This signifies a period of independence and adjustment, but you should not linger too long in mourning this relationship, as new opportunities are coming very soon, especially if you try a slightly different approach. 

In an ongoing relationship or marriage, this indicates things are at breaking point. Things are highly stressful, and one or both of you may need to walk away and have a pause, or perhaps a separation. This doesn’t mean that there cannot be a reconciliation, but a period of healing while you’re in a pause is essential so that you give your relationship the best chance of having a reboot. This does suggest a cold light-of-day appraisal and a relationship audit. It says don’t keep plugging on, doing the same old, same old. Take a break, let the dust settle, and pick up the pieces in a few weeks or months. 

Career meaning upright Five of Cups 

This may indicate a setback in terms of your career. Perhaps you made a wrong choice, a mistake in your calculations, or perhaps misread a situation. This card says that while you should acknowledge your error, put things right, and learn from it, you shouldn’t linger and obsess over the disappointment. Don’t overanalyse what you did; these things happen. It’s important to remedy the mistake as far as you can and quickly move forward to once again prove yourself and rebuild your reputation. 

If you’re looking for a job, you shouldn’t be concerned if you’re being stonewalled or experiencing a lot of rejections. Keep going; something is going to break for you. Don’t give up. Sometimes it’s important that you step away for a while so you can see the wood from the trees, because you may be applying for too many things without focusing your attention on what has the most potential and is the most fitting.

Health Meaning Upright Five of Cups 

This often indicates a recent health setback. Perhaps you broke your diet, fell off the wagon, or you haven’t been feeling your usual self. It indicates the importance of holistic wellbeing in remedying health problems. It’s vital not to pay too much attention to diet without attention to work-life balance or your spiritual life, or pay too much attention to your spiritual life but ignore your diet. Make sure that you tackle improving your health from multiple different angles and perspectives. 

Spiritual Meaning Upright Five of Cups 

This card encourages forgiveness and letting go. There’s nothing more powerful than releasing a situation and all those involved in it, and that involves a degree of forgiveness and being able to move forward. It’s important to understand that life has its ups and downs, for every success, there are many failures, and we only truly fail if we continue to dwell on the failures instead of seeking the successes. The only way to fail, really, is to keep looking back and not look forward. 

Feelings or Actions Related to the Upright Five of Cups 

This card encourages you to learn from your mistakes, but not to get stuck in self-recrimination or blaming others. Remember that when we were at school and we took exams, it was very rare that anyone, even the smartest kid in the class, got 100% or even 90%. The average was probably around 50%, and that’s a good way to look at life. We win some, we lose some, and so does everybody else. So, we have to forgive ourselves for the times we messed up, but we also have to forgive others. 

This encourages you to start looking forward, welcoming new opportunities, and working hard to drop the resentment and bitterness that may linger from things in your life that didn’t work out quite how you wanted. The positive message of this card is that, despite the fact that you may feel despairing and lonely, you’re going to bounce back, and the many opportunities will soon be revealed. 

Reversed Five of Cups Meaning 

In this case, the reversed tarot card is a powerful signal that you are beginning to leave a difficult situation in the past. This is a sign that you have made some bold decisions, picked yourself up after hitting rock bottom, and now you’re feeling a sense of momentum.

Events are moving forward in your life, perhaps in relationships, career, or your spiritual life, and you are beginning to feel that springtime has come after the winter. You may also be able to recognise the benefit of the failures and disappointments in a broader context, through what they might have taught you. 

Love meaning reversed Five of Cups 

In a love reading, this means that you are beginning to see a relationship in perspective. Perhaps you had a separation, a relationship pause, or you decided to give the dating game a break, and during this break suddenly things fell into place. You perhaps understood why relationships had failed, and maybe you recognised failings within yourself, such as boundary setting or lack of discernment, that led to setting unrealistic expectations which caused things to fail. 

This indicates you are in a good position to either reconcile with a partner, start a new relationship chapter in your marriage, or enter into the dating game because you understand your needs better, you’ve learned from your past mistakes, and you’re ready to see the warning signs when perhaps you or your partner are falling into negative patterns again. 

Career Meaning Reversed Five of Cups 

When you see this card reversed, it is a sign that you should be open to grabbing new opportunities in terms of career, but you should also accept a certain amount of risk. This is not a time to stick to your old comfort zones or paradigms. It’s time to be a little bit more bold, assertive, and to embrace new challenges if you really want to move your career forward. 

It represents that you are hopeful, and that the sentimentality or nostalgia related to a former career has lost its gloss, and you’re perhaps seeing the downside. If you have been struggling to find employment, this is a sign that you will be more successful, but remember the key is attempting things in a slightly different way as you don’t want to be too static or conservative in your approach. 

Health Meaning Reversed Five of Cups 

This is a powerful and positive indication that your health is beginning to improve, and that the suffering you might have recently experienced is coming to an end. This reversed tarot card is a strong indication that you are about to find a therapy or remedy that will make a remarkable difference, and you will be freed up from the issues that you were suffering from. However, it is also important to acknowledge the impact that holding on to resentment and an inability to let go could have had in making health conditions linger. This is also a cue that habits you might have had for many, many years have to go now.

Spiritual Meaning Reversed Five of Cups 

Spiritually, this tarot card can indicate that you feel trapped by some event or experience in the past that has shaped you. It does suggest that you may need a period of therapy in order to fully resolve something in your past, something that continues to replay in your head, causing you anxiety or fears. 

Sometimes this card means that an event in the present has triggered repressed feelings from a long time ago. It might have brought to the surface feelings of despair, abandonment, loss, or grief that were never adequately dealt with. Now is a time when you can positively deal with those issues, and therefore your life will be able to move in a powerful direction without that baggage. 

Feelings or Actions Related to the Reversed Five of Cups 

What’s great about this reversed tarot card is that it encourages you to connect with your integrity, know your values, and realise what you truly want from both relationships and a career, because this is key to success. The more you force situations which, in your heart, you know don’t feel right and aren’t going to satisfy you, the less success you will have. If you are able to bravely reach for those situations that would make you most happy and bring your life the most vibrancy, you are actually going to be much more successful. 

So, the message is don’t be scared to go after what you truly want. It also reminds you that within any success story there are numerous disappointments along the way, and one must simply bounce up, pick up the baton, and carry on. 

Past, Present and Future Positions for Five of Cups

Past

You may have experienced a breakup, a missed opportunity, or a project that failed to meet your expectations. The focus was on what was lost rather than what remained, and this emotional weight may have influenced later choices, making you more cautious or guarded. 

Present

You may be dwelling on past mistakes, feeling disappointed in yourself or others, or struggling to let go of what didn’t work out. There are opportunities, support, or emotional resources still available to you now, but they require a shift in focus. Healing is underway, even if it feels slow, and acceptance is the next important step. 

Future

You will be faced with the decision to either remain anchored to past sorrow or to begin truly moving on. New opportunities will emerge once you release resentment and grief. The future message is one of emotional resilience: while loss has shaped you, it will not define you, and renewal becomes possible when you choose to look forward rather than back.

Five of Cups — YES or NO Answer 

Upright: NO 

The Five of Cups upright leans strongly toward a NO. It reflects disappointment, regret, emotional loss, and focusing on what has gone wrong rather than what remains. The energy is heavy and backward-looking, suggesting that the outcome is not favourable at this time. 

Reversed: YES 

The Five of Cups reversed shifts toward Yes, especially if you are willing to let go of the past. This card suggests that you are ready to move forward with a healthier mindset. The answer becomes Yes when you stop focusing on what was lost and begin engaging with what is still possible. 

Advice and Message of the Five of Cups 

The advice with the Five of Cups is finding it in your heart to forgive. Remember the power of forgiveness, because not only is it spiritually the right thing to do, it also helps you to let go and move on. The more you don’t forgive, the more you get caught in bitterness, recriminations, and anger, and these toxic emotions can influence your health, your personal growth, and hold you in the status quo. Once you embrace forgiveness, it is like you have ripped up the anchor and are once again ready to set sail on your journey in life. Often, you will feel a huge sense of relief when you do it, so delaying forgiveness is hurting you more than the person you need to forgive. 

Summary 

The Five of Cups is a card that indicates there has recently been some sort of disappointment that is bothering you. You may feel rather deflated, pessimistic, or even in despair, but what this card reminds you is that while it is important to grieve and to process the emotions around a disappointment, you shouldn’t get trapped in that stage. You should quickly pick yourself up, dust yourself off, forgive yourself and others for their involvement, and start awakening to the brand-new opportunities that have arisen as a result of this loss. 

It’s important to realise that life is not plain sailing; there will always be things that don’t work out as we expected, but that’s often a cue that they weren’t meant to be, and that something even better is out there, but we haven’t glimpsed it yet because we were perhaps too fixated on one outcome. There is a saying that when God wants to punish you, he answers your prayers, so when your prayers aren’t answered, the deeper message may be that it wasn’t actually what was best for you anyway.