Letters From Love with Elizabeth Gilbert

Letters From Love with Elizabeth Gilbert

LETTERS FROM LOVE — With Special Guest Katherine May!

We practice by practicing

Elizabeth Gilbert's avatar
Elizabeth Gilbert
Nov 16, 2025
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Dear Lovelets,

Welcome to another installment of Letters From Love — where we are learning, together and in our precious solitude, how to speak to ourselves and write to ourselves with kindness and affection, rather than with cruelty and contempt.

What if you could behold yourself as a creature imminently worthy of love and mercy? What if you could see your struggles as noble (Earth School is hard, after all) rather than as embarrassing? What if you could reach out to yourself across the expanse of the entire universe (for indeed, that is how far away from myself I have felt at times) and say, “Hey there, little friend. How is your heart today? How can I help you today, dear stranger?”

Will it feel awkward and forced at first? Sure! Especially if you are only accustomed to hearing your own voice say to you such things as: You’re such a loser! You’re such a dirtbag! You’re such a lazy failure! You’re such a monster! Why do you suck at everything? You should be ashamed of yourself! — and many more such unkind sentiments that I could share from the mind-transcripts of my own personal history. Perhaps you have these transcripts, too?

Some people in this community, when they are afraid of writing themselves a letter from Love, say, But that seems so artificial, because it’s just my imagination.

I have news for you: so is the voice that tells you that you are a stupid idiot.

It’s all just your imagination.

So what if we learned to imagine better?

What if maybe for just five minutes, you allowed a more tender voice to have access to your imagination?

What if this is the week when you try writing yourself a letter from Love — and even if only one kind sentence comes through, what if that is the beginning of a whole new imagination?

Could be, right?

What is there to lose, except maybe some shame and self-hatred?

Our special guest this week is Katherine May, author of the books WINTERING and ENCHANTMENT, and The Clearing here on Substack. Katherine’s wise and gentle writing voice is matched only by her wise and gentle speaking voice. Please treat yourself to her letter. Its words and its cadence are hypnotic. Like many of us, she found the exercise awkward and artificial at first. And, like many of us, once she let the voice of Love in, she remembered it as a very, very old friend.

Let’s keep going!

Love,
Your Lizzy

Dear Love, how can I deepen my relationship with you?

Not to flex, honeyhead, but I am everything — so if you could perhaps deepen your relationship with everything, then you will deepen your relationship with me.

Does that sound overwhelming?

I promise you it is not an arduous assignment. In fact, it is not an assignment, but instead a very gentle invitation to a far more beautiful world than the often frightening one in which your mind sometimes abides.

The way to deepen your relationship with anything is to stop being afraid of it, first of all. To surrender into it. To trust it. You know from your own long experience, little heart, that you cannot express true warmth toward, or receive true warmth from, anything that you do not trust. Whatever you do not trust you are reduced to attempting to control. Whatever you do not trust, you are reduced to trying to survive. If you do not trust the experience of life itself, then you are reduced to trying to control it and survive it. Does that feel like love to you? Does that feel like a deepening of something precious and interesting? Or does it feel like a battlefield nightmare from which there is no escape, except through death, and even THAT feels scary?

Warm blanket of a girl, you can help us to find you more often — and you can help us to help you more often — by trusting us.

You like words, so go look up the etymology of trust.

If you look way back, you’ll see it comes from the Proto-Indo-European word “truewaz,” which means to be firm, solid, and steadfast. Do you hear the word “true” in there? Yes, the word “trust” and the word “true” are very old friends.

You may trust what is true, angel. And what is true will always be true. And the truth will always be firm, solid, and steadfast — no matter what else may change, or appear to change. And what is true, what you may trust, is that everything that is, is of love. Came from love, is made of love, will return to love. Which means love can’t go anywhere, except back to the beginning, which is also the end. Which means: infinite.

But let’s not get too obscure or intellectual or philosophical here, darling. Let’s get practical. You can deepen your relationship to us by listening even more closely for our voice, and by asking for connection and guidance even when you are away from your journal, even when there is no pen in your hand or laptop beneath your fingers. Just ask, “What would love have me know right now?” and trust that you will be told. And with each point of communication, with each time you touch us with your mind and hear a message (no matter how simple, even if it’s “drink a glass of water” or “let’s put down the phone”) the relationship will grow deeper.

Darling one, the other day you had a rather audacious thought, and we want to tell you that we heard it, and that we love it. “What if I just gave up resentment, fear, shame, and blame?” you thought. “What if I just put them down, the way, over the course of my life, I have put down alcohol, drugs, cigarettes, lying, sexual intriguing in order to get attention, or holding other people responsible for my life?”

You thought, “What if I realized that all these emotions — resentment, fear, shame, and blame — are just chemicals that alter my mood and mind, and maybe being sober now, really sober, means that I don’t use ANY mood- and mind-altering chemicals out of habit anymore . . . not even the ones that my system generates itself?”

You thought, “What if, every time I feel a jolt of resentment, fear, shame, and blame, instead of helping myself to it, taking a big toke off it, instead of treating myself to it, I just said: ‘No. I don’t do those drugs anymore’?”

You thought, “What would be left of me, if all the resentment, fear, shame, and blame were gone? Who would I be?”

We watched these questions move through your system, and we were pleased, as we watched you realize that — if all that was gone — you would just be something like sunlight moving across water. Which is, perhaps, what love feels like.

Deepen into this experiment, my love. Keep practicing, if you want to know us better. Really take these recent ideas of yours out into the world and practice them. Does it seem too difficult, to shed your old ways of thinking? To us, it does not seem as difficult as keeping your old ways of thinking.

Ask yourself whenever you feel your body clench in resistance to any circumstance (which is to say, any moment of life itself): “What would this moment look like if I was not holding onto fear? Who would I be in this situation if I was not assigning blame? What would my body feel like right now, if it was not burning with resentment? How would I move through this moment if I were suddenly, magically immune to being shamed or feeling shamed — if shame simply could not attach itself to me, because it had nothing to hold onto, because of how soft and open and trusting I have become?”

When the clench comes, stop. Just stop, unwind your body, slow your breath, and trust.

Don’t assume that the way you have always thought and behaved is the way you will always think and behave. Only look at how much you have transformed already! Only look at how differently you believe and behave now than you did 40, 20, even five years ago, as you have passed through one Earth School curriculum after another, learning what works (meaning, what increases serenity) and what does not work (meaning, what increases suffering).

What if you traded all those old habits of thought for the understanding that everything comes from love, is love, goes back to love — including you?

Give us a try, dear one, is what we are saying. Not only on this page, and in the privacy of your mind, or in this community, but in every single engagement of your life.

What have you got to lose, angel face? We have come this far with you. We have seen you through all your seasons and changes. Why not draw even nearer? Why not let us guide you in everything, big and small?

If you are ready for your miracle, we are ready for it too.

We cannot think of a single reason why not to keep going.

Prompt

Whether you’ve been here with us since the beginning or you are a newcomer curious about the voice on the other end of the pen or keyboard, I invite you to join me this week, get still, and write down this question: Dear Love, how can I deepen my relationship to you? I can’t wait to read your answers.

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