The Letters I Never Sent

On Heartbreak, Fantasy, and the Growth Found in Letting Go

“We’ll do it together… one, two, three!”

My friend and I sat in a booth at my favorite bar—me with a predictable old fashioned, them with a tropical mocktail, soft baile funk in the background, candles flickering. Our reunion, annual at best, was a joyful blend of whimsy and depth. It was clear we had both grown since our last meeting. So we did something symbolic to shed some old skin: we deleted our exes’ numbers.

Photo by Zane Persaud on Unsplash

I had mine saved with a stop-sign emoji to ward off temptation. Even though I felt that I had moved on, I couldn’t bring myself to delete her. But with a nudge—and the accountability from my friend needing the same—we both did it, formally severing ties to past versions of ourselves.

Years before, I was a freshman in college and a premiere soloist for the Berklee Charlie Chords, the all-male a cappella group. My ego was the size of a semi-truck because I had just unlocked my forever party trick: a full split. Every time I sang my solo—“Treasure” by Bruno Mars—I’d hit the ground with my legs spread as far apart as the Union and Confederacy.

We had a concert at another college, and the music director of the host group was a confident leader with a soft smile and a loud laugh. As they sound-checked, I immediately fawned, enamored by the first note she sang. I leaned to a friend and whispered, “I need her. I’m gonna make it happen.”

I walked up to her at the after-party with all the unearned confidence that comes with being 18 and delivered some glib pickup line I’m grateful I can’t remember. She smiled, laughed, and walked away as quickly as possible. I accepted the soft rejection but followed her on Instagram—just in case.

For years, through the intangible and infinite internet, I came to see her as brilliant. That’s still the word I associate with her most. Everything she posted was thoughtful, paced, intentional. She wrote about justice, reciprocity, and love as if those topics were sacred and the stakes were always life and death. Every few months I’d send an affirming message; she’d always respond. The conversations deepened, but we never met in person. In many ways, making it real terrified me.

If it’s real, then it can end.

Eventually we did meet again. Our March 2020 date was joyful—like hearing a symphony for the first time or the first bite of mac and cheese on Thanksgiving day. The next morning, I texted all my friends to tell them I had found “the one.” A week later, the country shut down. We lived on opposite coasts but kept “dating.” Hour-long FaceTimes, Lord of the Rings marathons, Valentine’s gifts. Through lockdown, I knew that as soon as it was safe, she’d be the first person I would make an effort to see.

When I began dating this woman, I began the practice of writing letters I knew I would never send. By getting the biggest feelings out first, I could zoom out and be kinder, more rational, and more grounded when the real conversations happened.

Letter #1 - Summer 2020 (deep in the fantasy)

I’ve thought a lot about our long conversation last week. I can’t remember being that candid about the future with anyone. It was scary and beautiful.

Through my eight years of knowing you, there are three moments when I felt myself falling in love with you.

The first was long before we were romantic, when you told me what you wanted out of a relationship. The love you described was a love I wanted—patient, kind, empathetic, justice-driven.

The second was our first date, when I went on an unnecessary rant about the restaurant putting a lemon peel in my old fashioned instead of an orange. When I looked up embarrassed, you were smiling—eager to see me passionate instead of dismissing something that could’ve seemed trivial.

The third was last week, when I was having an anxiety episode on the subway and you—without knowing you needed to—talked me through calming down.

When I picture our lives together, I think about trampolines in backyards. I fantasize about fences becoming shields instead of cages. I fear for the future our children might face because they will be relentlessly validated, and the world fears powerful children. I know we won’t let anything dim their light. They will be so strong.

Every time I speak to you, I’m convinced I’m talking to the woman I will spend the rest of my life with.

You’re going to make an amazing wife someday. And an even better mother.

Looking back, that version of us only existed because I believed in an “eventually” more than a now.

Letter #2 Spring 2021 (the one I came closest to sending)

Hey.

I need to get this out.

I feel disposable with you.

I’ve tried so hard to make this feel special, and outside of the occasional FaceTime, I don’t feel the effort returned. I’ve justified the silence, the distance, the weeks of nothing, but I can’t keep doing it.

Every holiday I’ve tried to make beautiful for you from 3,000 miles away. I never expected anything back; I just wanted you to feel loved. But you didn’t even text me happy birthday. That one really hurt. I’ve been left on read so many times, barely updated about your plans when we’re finally on the same coast, and I’ve felt like an afterthought this entire time.

I’m tired of talking to myself in your inbox. It’s frustrating to hear that I’m the kind of person you could marry and then watch days—sometimes weeks—pass without a word.

I still love you. The future I imagined for us is beautiful. But this limbo is eating me alive and turning me into someone I don’t want to be. Until you’re in a space where you can make me a priority, I think we have to stop whatever this has become.

When the truth finally arrived, it hurt less than the waiting ever did.

Letter #3 Summer 2021 (after the truth finally came)

I wish I had the courage to send this, but I can’t open that door again.

They say when you wear rose-colored glasses, every flag looks red. I was truly in love with you—a love I had never experienced. Agape and Eros. I spent hours imagining a future for us.

Learning you never cared for me was a beautiful heartbreak. I’m grateful. I don’t have to chase the fantasy anymore.

You write poems about all your exes. I’ve read so many of them. I think one is about me. I spent so much time reading your poetry and hating your exes. Now I think if you treated them the way you treated me, they were probably justified in the “cruelty” you conjured. I know I was never cruel. You constantly told me I was kind.

I hope you heal, and someone is able to be there for you in the ways you never allowed me to. If I were a weaker man you would’ve made me bitter. You made me sad, but I never lost myself.

If you told me you were sorry, I’d believe you. All I ever wanted was to believe your words and ignore your actions.

I wish I could hate you—it would be so much easier.

I think you are so brilliant. I will always find you brilliant.

I will never love anyone the way I loved you because loving you was scarcity and performance, not something that made me whole. I’m okay with never experiencing a love like that again. Love shouldn’t feel like that. The love I want must be rooted in mutual respect, and I won’t let myself be strung along again.

You are my rose-colored glasses.

I truly wish you the best.

Photo by Phil S on Unsplash

It took months to admit that what hurt most wasn’t losing her—it was losing the version of me who thought that was love.

Years later, I feel safe sharing these letters. Whenever I go on dates, the inevitable “So what are you looking for?” comes up. I smile and say, “Do you want the pretentious answer or the short one?” Everyone asks for the pretentious one.

In all my relationships—and in every part of my life—I want both integrity and happiness. I refuse to compromise one for the other. If the relationships in my life hit both, I’ll chase them relentlessly in whatever form they take.

Some lessons you can only learn by learning them. For that, I’ll always be grateful to her.

If someone says they’re going to choose you eventually, know that right now, you’re not being chosen. And that’s alright.

The truth is, this wasn’t the relationship that ruined me.

It taught me everything I needed to know.