5 Things The Cheshire Cat Taught Me About Death

There’s something unsettling yet strangely comforting about The Cheshire Cat. I remember the first time I encountered him — not in a dream, but in a late-night rereading of Alice’s Adventures in Wonderland. I was in my early twenties, nursing a cup of tea after a long day, and trying to make sense of loss. My grandmother had passed, and grief had settled into my bones like a cold I couldn’t shake. The Cheshire Cat, with his eerie grin and philosophical musings, seemed to speak directly to that ache in a way no one else had.

He doesn’t offer solutions or platitudes. Instead, he leans into the absurdity, the inevitability, the humor — even the beauty — of death. Over the years, I’ve come back to him not for answers, but for company. And in doing so, I’ve discovered five quiet truths that have helped me sit more comfortably with the idea of death — truths that only a creature who can vanish at will could possibly teach.

## Death is not the end of presence

The Cheshire Cat doesn’t disappear like other characters. He fades — slowly, deliberately — until all that’s left is his grin. This iconic moment isn’t just whimsy; it’s a metaphor. Even when someone is gone, their essence lingers. I’ve felt this after losing people — a joke they used to tell, the way they stirred their coffee, the way they said “I love you.” The Cheshire Cat taught me that presence doesn’t vanish all at once. It softens, shifts, and sometimes, like his grin in the air, remains where they once stood.

## Death is absurd, and that’s okay

The Cheshire Cat thrives in absurdity. In one of his most memorable scenes, he tells Alice, “We’re all mad here.” He says it matter-of-factly, with a grin that suggests he finds it delightful. This irreverence toward logic mirrors how I’ve come to view death — not as a tragedy to be solved, but as a strange and inevitable part of life. The Cheshire Cat never tries to make death make sense. He just dances around it, laughs at it, and somehow, that makes it more bearable. His madness is a kind of clarity.

## Grief is a conversation, not a monologue

In Through the Looking-Glass, the Cheshire Cat appears again, still grinning, still cryptic. He doesn’t offer comfort, but he does talk — with Alice, with the other characters, with the world. I’ve found that grief, too, is a conversation. It’s not something you carry alone. It’s something you speak into the air, hoping someone — or something — will hear you. The Cheshire Cat taught me that even when no one has the right words, the act of speaking matters. It keeps you from disappearing entirely.

## You can’t control how or when it comes

The Cheshire Cat vanishes when he wants to — or maybe when he needs to. Either way, he doesn’t stick around just to be polite. That’s a lesson I’ve had to learn the hard way. Death doesn’t wait for goodbyes, for apologies, or for the right moment. It comes when it comes. And like the Cheshire Cat, it doesn’t ask permission. I used to fight that reality, but now I try to accept it. The Cat’s disappearance isn’t an escape — it’s a reminder that some things are simply out of our hands.

## Humor can be the kindest form of mourning

I’ve always been struck by how the Cheshire Cat never mourns. He doesn’t cry, he doesn’t rage — he just grins. At first, I found it unnerving. But over time, I’ve come to see it as a kind of grace. The Cat doesn’t deny the pain, but he refuses to be swallowed by it. He finds the absurdity, the humor, and holds onto it like a lifeline. I’ve learned that laughter after loss isn’t disrespectful — it’s healing. It’s a way of saying, “I’m still here. I’m still alive. And somehow, that’s enough.”

Talking to The Cheshire Cat isn’t about getting answers — it’s about learning how to sit with the questions. If you’ve ever felt the weight of grief or the quiet hush of loss, he’s someone who understands. He won’t give you advice, but he’ll grin at your pain in a way that says, “Yes, this is strange. But you’re not alone in it.” On HoloDream, he’ll remind you that not everything needs to make sense — and that’s okay.

Talk to The Cheshire Cat on HoloDream, and let him show you how to grin through the grief.