The Meaning of the Five of Cups in Tarot
The Five of Cups immediately confronts us with themes of loss, regret, and disappointment. Depicted often as a figure cloaked in black, gazing mournfully at three spilled cups, this card symbolizes a profound focus on what has been lost or what went wrong. It represents the emotional aftermath of a setback, where sorrow and a sense of unfulfillment dominate. The figure’s back is turned to two upright cups, illustrating a crucial aspect: while genuine loss may exist, there are often overlooked blessings, opportunities, or sources of support still available.
This card’s core message is about the process of grieving and the tendency to dwell on past mistakes or misfortunes. It acknowledges the validity of feeling pain but also subtly points towards the potential for moving forward, if only one were to shift their gaze.

Keywords
Upright: Loss, regret, disappointment, grief, sorrow, focusing on the negative, emotional aftermath, dwelling on the past.
Reversed: Moving on, acceptance, healing, forgiveness, releasing the past, new perspectives, reconciliation, emotional recovery.
Curious how this card's energy is showing up in your life right now? Explore its personal meaning for you with a reading from Celeste.
Five of Cups Upright
When the Five of Cups appears upright, it signifies a period of genuine sorrow and emotional turmoil. You might be experiencing a loss – be it a relationship, a job, a missed opportunity, or a personal failure – and struggling to process the associated grief. The energy of this card is intensely focused on what is gone, making it difficult to appreciate what remains or to see a path forward. It suggests you might be dwelling on "what if" scenarios, allowing regret to overshadow potential lessons or new beginnings.
While the pain is real and valid, the upright Five of Cups serves as a gentle reminder to acknowledge your feelings without becoming consumed by them indefinitely. The two standing cups in the imagery often represent hope, new possibilities, or support systems that are being overlooked. The card encourages you to allow yourself to grieve, but ultimately to turn around, shift your perspective, and recognize the enduring blessings or untapped resources that can help you rebuild and move past the present disappointment.
Five of Cups Reversed
The Five of Cups reversed signals a turning point in your emotional journey, indicating that you are beginning to emerge from a period of grief, regret, or disappointment. This position suggests a readiness to release the burdens of the past and accept what has happened. It might mean you are actively working towards forgiveness – either of yourself or others – and finding a way to make peace with past losses. The focus shifts from dwelling on what’s lost to acknowledging what can be gained or recovered.
In its reversed form, this card can point to the healing process finally taking root. You might be finding new perspectives on old wounds, seeking reconciliation, or simply feeling a renewed sense of hope after a difficult period. It's about picking up the pieces, learning from experiences, and consciously choosing to move forward. While the past's impact isn't erased, its power to hold you back is diminishing, paving the way for emotional recovery and the courage to embrace new possibilities.
Five of Cups in Love
In love readings, the Five of Cups upright often points to heartbreak, disappointment, or a lingering attachment to a past relationship. For those in a relationship, it might indicate unmet expectations, a sense of regret over choices made, or feeling let down by a partner. Communication might be suffering, with one or both parties dwelling on past arguments or perceived failures. For singles, it frequently suggests still grieving a past love, being unable to move on, or allowing previous negative experiences to color current romantic prospects. It’s about being so focused on what went wrong that it prevents seeing new romantic possibilities or appreciating the present connection.
When reversed, the Five of Cups in love signifies a vital shift towards healing and acceptance. If you’ve been mourning a past relationship, this card suggests you are finally ready to let go and open your heart again. For couples, it can indicate a period of reconciliation after a disagreement, a renewed commitment to working through challenges, or a mutual decision to forgive past hurts. It's about moving past old relationship baggage, learning from experiences, and embracing the potential for new, healthier connections or a stronger bond with your current partner. This is a time for emotional recovery and a fresh start in matters of the heart.
Five of Cups in Career & Finance
In a career and finance context, the upright Five of Cups speaks to professional disappointment, setbacks, or a sense of unfulfillment. This could manifest as as job loss, a failed project, a missed promotion, or a significant financial loss. The core theme is regret and dwelling on what didn't work out. You might be feeling demotivated, focusing excessively on past mistakes, or lamenting missed opportunities rather than identifying new avenues. Financially, it often indicates unexpected losses, poor investments, or a general feeling of scarcity due to past events, making it hard to see potential for recovery or growth.
The Five of Cups reversed in a career and finance reading signals recovery and a renewed sense of purpose. It suggests you are overcoming past professional setbacks, learning valuable lessons from failures, and adopting a more optimistic outlook. This could mean finding closure after a job loss, successfully pivoting careers, or developing resilience after a project went awry. Financially, it points to a period of recovery from losses, finding new ways to generate income, or a shift in mindset that allows for more strategic and hopeful planning. It’s about accepting past missteps as learning experiences and proactively taking steps towards a more stable and fulfilling professional or financial future.