Love Letters I Never Sent

Letters I Never Sent
By Lila Hart

They’re still in the shoebox beneath my bed—creased envelopes, yellowed with time, addressed but never mailed.

Each letter begins the same: Dear Eli…

I wrote the first one the night you left for college. The rain tapped on my window like your fingers used to on my shoulder when you had something secret to share. I remember sitting cross-legged on my bedroom floor, pen in hand, heart wide open. I wrote about how proud I was of you. How I knew you’d conquer the world with your laugh and the constellation of freckles on your cheek that danced every time you smiled.

But I never sent it.

Back then, I told myself it was because you were moving on. That my words would just be another weight in your already full suitcase of dreams. But the truth? I was scared. Scared that once I sent that letter, you’d know.

That you’d know I was in love with you.
We grew up as next-door neighbors, our lives stitched together with bike rides, scraped knees, and summer lemonade. I was the quiet one with ink-stained fingers. You were the firecracker—always loud, always bright. You made the world feel less lonely, Eli.

I watched you fall in and out of love with people who weren’t me. I listened patiently as you spilled secrets over cups of coffee, your voice soft and unsure. Each time, I’d write you a letter. I’d pour my heart onto the page, then fold it neatly, seal it, and slip it into the box.

There are 42 letters in there.

Forty-two moments I could have changed everything, but didn’t.

One of them is dated July 19th, 2019. The night we almost kissed. Do you remember? We were both tipsy from too many wine coolers at Jamie’s rooftop party. You pulled me aside, told me I always made you feel safe. Your fingers brushed mine. You leaned in. My heart screamed finally.

But you stopped. “I can’t,” you whispered. “Not tonight.”

I smiled like it didn’t shatter me. When I got home, I wrote, If you had kissed me, I would’ve kissed you back. I would’ve told you everything. But I didn’t. I just added it to the box.

Years passed. Life moved forward. We drifted, as people often do. You met someone. Got engaged. I clapped the loudest at your engagement party, pretending I didn’t feel like a guest at a celebration of my own heartbreak.

And yet, I kept writing. Even when it made no sense. Even when I told myself it was time to let go.

I wrote my last letter on your wedding day. It's dated August 14th, 2022.

I wrote: I hope she sees what I saw. I hope she loves you with the same quiet intensity that I did. And if you ever find these letters, if by some strange twist of fate you read them—please know, I never expected anything. I only ever wanted you to be happy. Even if it wasn’t with me.

I never mailed it. Of course I didn’t.

But lately, I’ve been thinking about how we always believe timing is everything. That fate has a plan. But maybe love isn’t always about timing. Maybe it’s about courage. And I lacked it.

I don’t know if you’ll ever read these. I don’t know if you’d even recognize the version of me who wrote them.

But I’m tired of hiding.

So this is my forty-third letter. And this one, I’m finally sending—into the world, into the ether, into the hearts of anyone who’s ever loved in silence.

Maybe someone out there will read this and find the courage I never had.

And maybe, just maybe, that’s enough.