Why We Keep the Letters We’ll Never Send

The drawer was jammed again.

I yanked at it, muttering under my breath, and a thin cascade of envelopes slid forward, fanning across the floor like pale autumn leaves. They smelled faintly of paper and time—slightly yellowed, edges curling inward, some stained with coffee rings or thumb-smudges.

They were my letters.

Not bills. Not cards from friends. Not invitations or receipts.

But the ones I had written and never sent.

For a moment, I sat cross-legged on the floor, just staring at them. I didn’t know what had made me keep them all these years. It was an odd ritual—writing something that would never be read, folding it neatly, placing it in an envelope as if it were real, and then… hiding it away.

Some people journal.

I write letters to ghosts.

The earliest was dated June 14, 2007.

The handwriting was my high-school scrawl—messy, impatient, all loops and tilted lines. It began:

Dear Mom,

I’m not mad at you. I think I’m mad at the space between us. It feels like an ocean now, and I’m not sure if I’m supposed to swim or let myself drown.

I remember writing it in my bedroom with my headphones on, music blasting to drown out the sound of her talking on the phone in the kitchen. She’d been laughing at something—probably with her new boyfriend—and it had hit me, sharply, how little of her laughter was shared with me anymore.

I never gave it to her.

Partly because I was afraid she’d dismiss it, and partly because I didn’t want her to know she had hurt me that much.

It’s strange—keeping a letter like that isn’t about hoping the person will read it someday.

It’s about preserving the moment you finally admitted to yourself how you felt.

Some letters were heavier to touch than others. This one was thick, the paper warped from where my pen had pressed too hard.

Dear Adam,

It’s been three years and I still think about your hands. Not your smile, not your voice—your hands. The way you cupped them around your coffee mug in winter, like you were afraid of losing warmth. The way you touched my back in a crowd, not to pull me closer, but just so I’d know you were there.

We’d been more than friends but less than a couple, a kind of purgatory I convinced myself was romantic. I wrote the letter the night I found out he’d gotten engaged. I never mailed it, of course. I think part of me believed that if I kept it, I’d also keep him—at least the version of him that existed in my memory.

Letters are like photographs that way.

They freeze a version of someone that can’t be touched by the reality of who they became.

I’ve read enough psychology blogs to know what the experts say:

We keep unsent letters because they are safe containers. They hold feelings too sharp to keep inside, but too dangerous to share out loud.

But I think it’s more than that.

Every letter I’ve never sent feels like a conversation between two versions of myself: the one who was too afraid to speak, and the one who finally found the courage to write.

They are proof that I did feel deeply once, even if no one else knew it.

And sometimes, on the bad days, that’s all I need to remember—that I have been alive enough to hurt.

There’s one that still makes my chest ache when I touch it.

Dear Dad,

I’ve been dreaming of you lately. In one of them, you were standing in the rain without an umbrella, laughing like it was the best thing that had ever happened to you. I woke up crying, because I realized I couldn’t remember the sound of your laugh in real life.

I wrote it on the anniversary of his death. Not the first year—that one I spent in numb disbelief—but on the fifth, when the sharpness had dulled and I was left with something heavier: the fear that I was forgetting him.

That letter lives in its own envelope, tucked inside a book of poetry he once gave me. I never reread it, but I can’t throw it away. It’s the closest thing I have to a conversation with him.

Not all the letters were to other people. Some were to future versions of me.

One read:

Dear Me (age 30),

If you’re reading this, it means we survived. I hope you’re not still afraid of being alone. I hope you’ve stopped measuring your worth by who stays and who leaves.

I was twenty-two when I wrote it, freshly heartbroken and convinced that I’d missed my only shot at love.

It’s funny, looking back now. I didn’t know then that I’d write many letters to future selves, each one a breadcrumb trail of who I’d been. They remind me that I’ve grown, even when it feels like I haven’t.

There was a night, a few years ago, when I almost burned them all.

I had just moved into a new apartment after a messy breakup. The drawer was sitting on the floor, and the sight of it made me feel sick. These letters felt like an anchor to a past I wanted to sever.

I lit a candle. I even held one letter above the flame, watching the edges curl and blacken. But I couldn’t do it.

Not because I was still attached to the people in them, but because destroying the letters felt like erasing me.

Every unsent letter is a fossilized version of my truth—raw, unpolished, unperformative. They are the only times I have spoken without thinking about how I would sound to someone else.

A month ago, I wrote a new letter.

Dear Clara,

You don’t know me yet, but you will. I’m the person you’ll become in ten years. I want you to know something: you will lose people you think you can’t live without, and you will live without them. Not because you stop loving them, but because life will make you.

I sealed it, dated it, and put it in the drawer with the others.

Maybe one day I’ll open it. Maybe I won’t.

That’s not the point.

The truth is, we don’t keep these letters because we secretly hope to send them one day.

We keep them because they are monuments to the moments we couldn’t say what we felt in real time.

They’re not for the people we wrote them to.

They’re for the people we were when we wrote them.

And maybe that’s the most honest thing I’ve ever admitted:

I keep my letters not to hold onto you—but to hold onto me.