Five of Cups as Obstacle or Challenge (Upright & Reversed) Tarot Card Meaning

The Five of Cups is the card of grief, loss, sadness, and disappointment. This card shows a man crying over three knocked down cups. He is so absorbed in his loss that he doesn’t see that he has two upright cups behind him. He is missing the opportunities that are still available to him. 

The Five of Cups reminds us that grief is a natural part of life. It is normal to grieve over our disappointments and failures. Challenges and losses are part of the journey. However, it is important to not be so wrapped up in the negative that we do not see the positive in our situation. The Five of Cups reminds us to authentically grieve, but also to see how we can use this moment as a learning opportunity to move forward.

Upright Five of Cups as an Obstacle or Challenge

If you are asking about an obstacle or challenge, and you draw the Five of Cups, it means that feelings of loss, grief, or disappointment may be affecting your current situation. This card is often associated with emotional upheaval or sorrow, suggesting that you may be struggling with the after-effects of some loss or disappointment. It is important to process these feelings, but also crucial to recognize that this is a temporary state, and healing will come in time.

The Five of Cups as an obstacle or challenge can represent focusing on past failures or losses instead of recognizing the opportunities still available to you. It indicates a tendency to dwell on what’s been lost, overshadowing the positive aspects or potential that still remains. This card urges you to shift your perspective, turning away from past disappointments and focusing on the opportunities and blessings that are still within your reach.

If you are asking about a potential relationship, the Five of Cups as an obstacle or challenge means that previous heartbreaks or emotional baggage may hinder the development of a new connection. This card suggests that past relationship failures or disappointments might be affecting your ability to trust and open up to someone new. It’s crucial to acknowledge these feelings, but also to understand that each new relationship brings its own potential for happiness and fulfillment.

If you are asking about an existing relationship, the Five of Cups as an obstacle or challenge means that unresolved emotional pain or feelings of loss may be causing strain between partners. This card can suggest that one or both partners are dealing with past hurts or losses, which may be impacting the relationship negatively. It encourages both partners to communicate openly about these feelings, working through them together to heal and strengthen the relationship.

If you are asking about an ex, the Five of Cups as an obstacle or challenge means that lingering feelings of sadness or regret may still be affecting your ability to move on. This card suggests that you may still be grieving the end of the relationship or feeling regret over what could have been. It’s important to allow yourself to feel these emotions, but also to recognize that healing is possible, and there are still opportunities for happiness ahead.

If you are asking about career and financial matters, the Five of Cups as an obstacle or challenge means that past setbacks or disappointments may be holding you back from achieving your goals. This card suggests that you may be focusing on past failures or missed opportunities, causing you to feel stuck or unmotivated. However, it also serves as a reminder that not all is lost and there are still opportunities for success if you can shift your focus towards the future.

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Reversed Five of Cups as an Obstacle or Challenge

If you are asking about an obstacle or challenge, and you draw the Five of Cups reversed, it means that acceptance, healing, and the ability to move on from past difficulties are key to overcoming the issue. This card suggests that you are starting to make progress in dealing with past disappointments or losses. It signifies a time of personal growth, indicating that you’re learning to leave the past behind and look forward to new possibilities.

The Five of Cups reversed as an obstacle or challenge can represent emotional healing, personal growth, and the capacity to forgive and move forward. The presence of this card implies that you may be on the path to overcoming past hurts and disappointments. It’s a reminder that healing is a process, but with patience and perseverance, you can move beyond the pain and toward a brighter future.

If you are asking about a potential relationship, the Five of Cups reversed as an obstacle or challenge means that by healing from past emotional wounds, you can create a healthier and stronger connection with a new partner. This card suggests that it’s important to address and heal from past emotional hurts before entering a new relationship. By doing this, you’re more likely to form a connection based on mutual trust and understanding, leading to a more fulfilling relationship.

If you are asking about an existing relationship, the Five of Cups reversed as an obstacle or challenge means that by addressing and overcoming past emotional pain, both partners can strengthen their bond. This card highlights the importance of open communication and mutual understanding in healing emotional wounds. By working together to overcome past difficulties, you can foster a stronger and more resilient connection.

If you are asking about an ex, the Five of Cups reversed as an obstacle or challenge means that forgiveness and acceptance of past experiences can help you find closure and move on with your life. This card indicates that you’re on the path to healing and moving on from past hurts. By forgiving and accepting what happened, you can close this chapter and open yourself up to new experiences and opportunities.

If you are asking about career and financial matters, the Five of Cups reversed as an obstacle or challenge means that by learning from past setbacks and focusing on future opportunities, you can achieve professional and financial success. This card suggests that past failures should not be seen as a hindrance, but rather as learning experiences. By applying these lessons and focusing on your future goals, you can use these past experiences to fuel your progress and success.

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Conclusion

For relationships and feelings, the Five of Cups represents grief and loss. These challenges are a normal part of life and any relationship. It is not the fact that we have grief and loss that matters, but how we respond to it. The Five of Cups reminds us that we can turn our most difficult moments into learning opportunities. 

If you find yourself needing further clarity in your relationship matters that go beyond reading for yourself, Sibyl offers unlimited tarot readings on love & relationships, as a neutral and objective third party.