Five of Cups
i. The Nutshell
Upright
Are you ruminating on what didn’t work out, or holding onto regret? This card signifies sadness, disappointment, and shame that can weigh you down unless you make changes. There’s an emphasis on focusing on the loss rather than the opportunity that can be gained from it, as indicated by the three spilled cups and the oblivion to the two remaining upright. This card doesn’t attempt to sweep or sidestep grief, but it does ask you to acknowledge where the sadness lies and to evolve in some way from it. You may be replaying mistakes, blaming yourself, feeling drained and withdrawing from life. To be honest, this card could be a book in itself because in my opinion, most growth happens from struggle and hardship, making this card your flagstone to a pivotal point. Whilst its minor arcana, make no mistake in judging its spectrum of severity. This can be anything from a spilled cup of tea to the unimaginable, but the message remains.
Whether you’ve gone through a break up, circling regretful behaviour you know you’ve since learned from, or beating yourself up for a lost opportunity, start by identifying your emotion to gain perspective and acceptance. In most situations, not everything is lost and what is meant for us doesn’t bypass us. There are multiple ways to reach something if we’re open to finding the value, growth or learning once we’ve healed enough to be able to take a step back to see it. Regret is futile and binds us to rumination, stagnation and self defeating prophecies. Shame is a common reaction, but it’s debilitating because it feeds the belief we are fundamentally flawed for doing ‘the wrong’. This belief keeps us in the negative cycle, and prevents us from seeing new perspectives and evolving - which makes the whole experience pointless. Meaningless pain is harder to bear than pain with purpose, as it offers no chance for growth or inspiration.
Keywords: Avoidance, detachment, loss, grief, pessimism, regret, sadness, failure, disappointment, fixation, emotional withdrawal
Translation: Validate your pain but don’t allow it to define your life.
Reversed
The reversed Five of Cups indicates that you are working through your emotions based on acceptance and re-engagement of life after overcoming, or beginning to - something that was weighing you down. This might involve reconnecting with others, finding new meaning in your emotions or not letting regret affect your life in the present since you know the past cannot be changed.
As you begin the healing process, this card highlights the need to continue to work on perspective and to stay open to new possibilities. Feelings fluctuate and can easily control you if you’re not compassionate and accepting of yourself for having them. As you accept the situation with kindness for what it is, be open to emerging insights that guide you toward growth and change. Remaining present takes practice but is rewarding. Acknowledge the strength you've gained by supporting others through their challenges by offering them your courage, insight, and experience.
Finally, remember healing is complex and wholly individual. There’s no time limit, markers or defined pace. Others may have opinions about how quickly or slowly you’re moving through your emotions, but those judgements reflect their own unresolved pain and not your process. If you're moving quickly, they might call you shallow or detached. If you're moving slowly, they may label you stuck or hopeless. Either way, their lens is not your truth, so trust yourself with compassion and be around those who respect and support you.
Keywords: Overcoming setbacks, forgiving yourself, moving forward, acceptance, renewal, emotional release, perspective
Translation: Healing begins when you stop battling with what already happened.
ii. Illus-traits
A quick glance at the symbolic language of the Four of Cups in the Rider-Waite-Smith deck:
Shrouded Figure Facing Spilled Cups – The figure’s posture reflects grief, shame, or deep regret. This fixation point reflects how unresolved pain obscures everything.
Three Spilled Cups – Representing emotional loss whilst urging us to face pain for personal growth and reflect on the internal narratives.
Two Upright Cups Behind – The parts of us unbroken by loss that are ready for us to notice when ready with new perspective, opportunity and hope.
Dark Cloak and Hidden Face – A visual metaphor for shame and internalised belief that we are what happened, thus creating cycles of self abandonment and emotional paralysis.
River and Bridge in Background – These indicate the potential for movement between our inner and outer worlds. However, the figure's current stance makes that journey feel distant.
Castle Across the Water – A symbol of safety, integration, and life beyond the wound. Healing begins with acceptance and the capacity to believe again.
iii. Influences
Planetary Influence
Mars illustrates how grief affects identity and creates a need for presence, while the Sun helps restore energy by encouraging enjoyment and self-expression. Venus highlights how grief reshapes relationships, often leading to emotional honesty and mutual respect. Uranus ousts buried emotions and brings sudden insight, offering a chance to break inherited patterns. Pluto intensifies this process by revealing hidden attachments and encouraging change.
Natal Houses
The First House pushes you to redefine what matters to you beyond your loss, whilst the Fifth house offers healing through creativity and rediscovering happiness. The Seventh House shows how our interpersonal style is affected by unhealed issues such as codependence, the Eighth House becomes a catalyst for transformation whilst the Twelfth points to generational change.
Astrological Signs
The Five of Cups represents Scorpio's strength to confront pain and become stronger. Aries encourages the reclamation of self after loss and moving past regret. Leo inspires emotional healing through courage, Libra highlights emotional balance and merges individuality with connection. Aquarius offers the needed distance to reflect on past patterns and see things more clearly.
Numerology: Five
Five marks disruption, the mid-point in a cycle, emotional upheaval, and the challenge of change. Five wants you to experience as much of your life path as possible and make the most of every opportunity good and bad that comes your way whilst communicating what you’ve learned to help others improve their lives.
Element: Water
Water holds memory, emotion, and intuition. The Five of Cups encourages honest reflection without drowning in your pain. Healing starts when you acknowledge your feelings without becoming overwhelmed.
iv. A Day in the Life of the Five of Cups
Well That Escalated Quickly
You go through the motions of life but regret, guilt, or the feeling that something important has been lost resides underneath everything you do like a black cloud that won’t go away. You avoid thinking, and certainly conversations about it because revisiting the past feels too overwhelming, uncontrollable and pointless. You’re lethargic and small decisions have become heavy. You’re emotionally at sea and physically unanchored. You know you need help, but even if there was a point to that, where would you start given how you feel.
Adjusting the Knobs
You start to see the cost of holding onto unresolved feelings and realise that isolating yourself, over-analysing and detaching may not be that healthy. You begin to question what you’re grieving and whether a part of yourself for making choices that led to this are part of it, or the significance of something that used to matter but now doesn’t. You’re not moving on, but can see that being more present is giving you a moment to see a bigger meaning.
Unsubscribed from Self-Sabotage
You allow yourself to feel what’s there without making it your identity. Instead of rehearsing doom and gloom assumptions, you reflect on what they’re teaching you. The two metaphorical upright cups in the card become visible and this inspires hope that your experiences have not defined you - and that bridge is a bit closer. You begin to selectively engage again whilst considering that healing might involve learning rather than forgetting.
Writing the TED Talk
You respond to emotion rather than avoid it. Loss is still part of your story, but it no longer defines your choices from the place of victim-hood. You’re communicating clearer because you’re feeling clearer. Whilst you’re feeling a healthy kind of self protection, you are now engaging in new opportunities. You know these won't replace what you’ve lost because you're not expecting them to. Instead, you're looking at them with a fresh perspective that comes from emotional balance and availability; simultaneously holding memories and possibilities.
v. Working with these Energies
The Five of Cups encourages you to look within and acknowledge your losses while also appreciating what you still have, even if that’s unknown opportunities you’re yet to be offered.
Emotional Inventory - Recall a time you experienced regret or emotional loss. What did you internalise about yourself because of it? Were there beliefs about failure, responsibility, or worth that took hold? What remains unresolved, and what have you learned from navigating through it?
Recognition versus rumination - Think of a moment when you repeatedly replayed a past event. What were you hoping to resolve by doing so? Notice where you mind goes with that question. Can you distinguish between reflection that brings insight, and rumination that reinforces powerlessness and/or defensiveness?
A measured return - Identify one low-risk way to re-engage. This may be a conversation you've been avoiding, or simply acknowledging that all is not lost. Pick one area to start with, either personal or relational, where you can be present even if not everything is settled.
Anchor in Awareness - Notice how your body responds when grief or memory arises. What does tension or stillness reveal? Staying present means allowing what’s there to be seen without collapsing into the emotional sink hole. This is where integration begins.
vi. Building Skills
Unhooking through Grief
When we lose someone or something we held dear, the mind often loops through memories, regrets, and imagined scenarios. Some thoughts hold meaning; others simply keep pain alive without offering understanding. Instead of avoiding or investing in these thoughts, notice them. What do they reveal about what mattered to you and what mattered to the person you lost?
Rather than trying to silence the pain, reflect on what values your person lived by that you respected. Where do those values overlap?
Grief often reveals what was deeply meaningful, so by identifying those shared values, you’re able to carry something of the person forward that honours the bond you shared through committed action.
Shapeshifting
If someone you lost valued honesty, creativity, or being there for others, consider how you might embody those values now and in your own way. Maybe you initiate a conversation you’ve been avoiding, or return to a creative practice they once encouraged.
Where can you nurture the value and make a genuine enquiry as to whether something can continue to be part of your life albeit in a different way?
vii. Embodiment
The Five of Cups: Recovery in real time
Scent - What smell brings you back to a memory that carries both ache and meaning? The pages of a book? The air in a hospital room? A familiar food you haven’t made since the loss?
Body - Where do you hold grief that hasn’t had space to move? Sinus pain behind the eyes? A heaviness in the lungs? Root chakra related issues? And where does the first sign of relief show when you’ve given that grief attention?
Soundtrack - What sound allows you to sit with sorrow without being consumed by it? Is it the hum of an appliance, a voice message you’ve saved, or a piece of music that helps you feel but doesn’t require more?
Action - What one action honours the memory of what’s gone while helping you re-engage? Sorting through a drawer, revisiting a place, hand-writing a letter to mark the reality of loss and continuity?
Nature Cue - Notice how nature takes in emptiness without falling apart, like a tree hollow or burrow where something once lived.
viii. Your Impressions
Look at the Five of Cups in your own deck or the image above. Simply notice, and resist the urge to interpret, instead allowing the illustration to serve as a mirror:
What pulls your attention first? The figure’s posture, the spilled cups, or the two still standing?
Notice how your body responds. Do you feel heaviness, distance, tension, a desire for something?
What might this card reflect about how you process emotional pain or regret? Are there parts of your experience you overlook because of shame, or grief you avoid because it feels too final?
Which emotions are still waiting to be acknowledged?
ix. Intuitive Meaning
Use this space to reflect on what the Five of Cups means to you personally:
What is this card inviting you to face in your experience of loss, regret, or unexpressed emotion?
Where might you be holding on to something that no longer needs protecting, and what could move if you made space to acknowledge both pain and potential?
When have you felt detached or numb to avoid feeling too much? And what would it take to let even a small part of that grief move?
Applied insight with a three-card reading using the Five of Cups as your anchor:
What part of my grief or emotional pain am I still carrying alone?
What stops me from seeing what is valuable or meaningful?
What allows me to respond compassionately to what hurts?
Let your cards talk and note your feelings as your answers unfold, writing your own words below:
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x. Closing Reflection: Track Your Evolving Lens
Your relationship with each card will grow over time because it’s meant to shaped by your life. Consider the prompts below to revisit and reflect.
What I thought this card meant when I first pulled it: —————————————————
A recent experience that changed how I see it: —————————————————
How I feel about it now, in my body or life: —————————————————
What surprised me as this card kept showing up: —————————————————
One way this card is living in my life right now: —————————————————
If this card visited me today as a guide, what would it want me to remember? —————————————————
Revisit these after a week, a moon phase, or a meaningful moment. Let the card evolve as you do.
If you feel a quiet sense of recognition, curiosity and want to explore it, browse the sessions page for what feels right.