The Five of Cups — Loss & Regret Playlist
The Five of Cups embodies grief. It’s heartbreak, regret, and the ache of staring at what’s gone instead of what remains.
This card honors the necessity of mourning. But it also whispers that even in loss, hope still flickers. The cups left standing matter just as much as the ones that spilled.
And that’s where music comes in. A playlist for regret, like this one, acts as a spell. It holds your sorrow, giving space to grieve, while gently pointing you toward healing.
But first, let’s talk about what this card means.
The Five of Cups in Tarot
In the Rider–Waite–Smith deck, the Five of Cups depicts a cloaked figure mourning over three spilled cups, unaware of two still standing behind them. It is grief in sharp focus.
At its core, this card represents:
✨ Loss and Regret — the pain of endings and disappointments.
✨ Mourning and Grief — honoring what is gone.
✨ Resilience and Renewal — remembering that not all is lost.
When this card appears in a reading, it encourages you to grieve fully but also to notice what remains upright.
Music as Magic
To me, music is one of the simplest kinds of spellwork. A playlist can set the tone for an afternoon of creativity, a ritual, or even just a mood shift. The songs we choose become the energy we’re weaving around ourselves.
The Five of Cups playlist is one I imagine playing while:
Sitting with grief and honoring what has been lost.
Journaling to release regret and name what still stands.
Lighting a candle to honor endings and heartbreak.
Meditating on resilience even in sorrow.
It’s music for mourning, memory, and gentle renewal.
The Playlist
Here’s the soundtrack I curated to capture the essence of the Five of Cups:
Back to Black – Amy Winehouse
Amy Winehouse opens this playlist with smoky defiance, a declaration of grief that refuses to hide its edge. “Back to Black” sets the stage for mourning love lost, capturing both the sharp ache of absence and the stubborn insistence on feeling every ounce of sorrow fully.Someone Like You – Adele
Adele’s ballad is heartbreak distilled. With soaring vocals and devastating honesty, she sings of acceptance that still cuts like a knife. It’s the raw ache of realizing love has moved on, the bittersweet attempt to bless someone else’s future while still bleeding from the wound of goodbye.I Was a Fool – Tegan and Sara
This song holds the quiet pain of self-blame. Tegan and Sara’s harmonies weave regret with tenderness, confessing the ways we replay our mistakes when love slips away. It’s not just about loss but about the haunting “what ifs” that echo long after the end.Disarm – Smashing Pumpkins
With its aching strings and vulnerable delivery, “Disarm” tears open hidden wounds. The song speaks to innocence lost and the weight of choices that can’t be undone. It sharpens the playlist’s edge. Grief isn’t only about others; it’s also about the pain we carry inside.Skinny Love – Bon Iver
Bon Iver’s falsetto cracks under the weight of fragile love unraveling. Sparse and haunting, “Skinny Love” is a plea wrapped in resignation, the sound of something once tender collapsing under its own thin scaffolding. It’s heartbreak stripped bare, letting silence speak louder than words.The Night We Met – Lord Huron
This track is pure longing, a desperate wish to rewind time and undo the loss. With ghostly instrumentation and aching vocals, “The Night We Met” embodies regret so heavy it lingers like a haunting. It’s the moment when grief feels inescapable, pulling the listener deeper into its shadow.River – Joni Mitchell
Joni Mitchell’s classic offers sorrow in motion, the yearning to escape one’s own heartbreak by disappearing into something vast and cleansing. “River” shifts the playlist toward reflection, making space for tears that flow freely, carrying away bitterness while leaving behind the still ache of longing.Everybody Hurts – R.E.M.
R.E.M. extends a hand in the darkness. The song is an anthem of shared sorrow, reminding us that pain is universal and fleeting. Its gentle rhythm and heartfelt lyrics offer the first breath of solidarity in the playlist, urging listeners to lean on compassion, to keep going, and to trust that even despair softens with time.I Know It’s Over – The Smiths
Morrissey’s lament closes with brutal honesty: the bitter acceptance that something beloved has come to an end. “I Know It’s Over” refuses to soften its blow, but within its bleakness is catharsis. By facing the stark truth, the song delivers the release of naming loss exactly as it is.Everybody’s Got to Learn Sometime – The Korgis
The playlist ends with melancholy wisdom. Gentle and hypnotic, this track suggests that heartbreak is part of being human, a lesson we all must face. It leaves listeners not in devastation, but in bittersweet acceptance—the recognition that sorrow reshapes us, and in that reshaping, life continues.
Journal Prompts for the Five of Cups
If you want to go deeper into the energy of this card, try reflecting with these prompts:
What am I grieving, and how can I honor that grief with compassion?
What lessons or growth might exist in my experiences of loss?
Which blessings or opportunities might I still be overlooking?
If you’d like to explore these prompts more deeply, I’ve created a free worksheet to guide you through the process.
Blog Rewards Program
The Five of Cups reminds us to honor loss while seeking resilience. 🌧️ Get the free Grief Insight Kit with a 3-card spread and prompts to explore sorrow, release, and renewal. Available in the Blog Reward Program.
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Bringing the Five of Cups Into Your Life
This playlist creates sacred space for mourning and healing.
Candle Ritual: Light a black or blue candle for what you’ve lost.
Grief Journaling: Write about regrets while listening.
Compassion Practice: Place a hand on your heart, breathe, and send yourself kindness.
Affirmation Work: Say, “I honor my grief. Renewal is possible.”
By making listening intentional, you transform music into magic.
Final Thoughts
The Five of Cups honors the ache of loss. This playlist is here to walk with you through sorrow while gently reminding you of the cups still standing.
So put on the music, light a soft candle, and let yourself feel. Let the songs hold space for grief while also whispering that healing is possible, and that even in mourning, you are not broken but becoming.
✨ Want to go deeper? Journal on “what is still here to support me, even in loss?” while you listen.
