Connie Converse and the Archive of Almosts by Jack Essner

“He went around with his heart unfurled,

The one and only Playboy of the Western World.

You could fall in love with everyone you meet, 

When you'd walk with him down the street.”

— Connie Converse, “Playboy of the Western World,” How Sad, How Lovely (2009) 

We want endings that explain things—some neat emotional thesis that justifies all the time spent thinking about someone. We want the wondering itself to mean something. But some people simply remain unsolved: crushes, the stranger on the subway who held my eye a second too long, that boy from the LES, Connie Converse.

What’s weird about discovering her music is that I don’t remember how it happened. No tortured man played one of her songs for me in his nightmarishly decorated Bushwick apartment. Nobody insisted I listen to "How Sad, How Lovely." Connie just drifted in one night through the cracks of the internet, and suddenly she was sitting in the middle of my brain, barefoot, guitar in hand, completely unbothered by the fact that I had not invited her in. 

Born Elizabeth Eaton Converse in 1924, she spent the 1950s in a Greenwich Village studio apartment writing and recording songs that now feel strangely ahead of their time—intimate, quiet, witty, like they were already leaning toward a genre that hadn’t quite named itself yet. Her music has this eerie familiarity, like it belongs just outside of regular life, something you swear you’ve heard before in sleep or in another version of yourself. And then, in August 1974, just after turning fifty, she packed her car, wrote a handful of letters, and disappeared. 

Discovering Connie seems to happen in phases: first, I was enchanted; then suspicious; then deep in Reddit threads at 2 A.M. trying to reconstruct a life alongside strangers equally unwilling to let her vanish completely. I kept returning to her, as you do with certain people in this city, without quite choosing to. There's something lonely about missing someone you never knew, in wanting explanations from a person whose silence has long outlived their voice. 

The internet has become its own archive of almost-answers about Connie: theories, timelines, people circling the same absence. Because the question never really goes away: where did she go? 

Dating in New York, especially, feels littered with Connie Converses—people we know just enough to become obsessed with and never quite enough to actually understand. Music starts to sound like them, and Hinge starts to feel less like romance and more like an archive of “almosts.” She reminded me of a certain kind of New York man: stylish, hard to pin down, easy to overthink, never quite real enough to stop affecting you. It’s mystery disguised as intimacy. 

It’s not Connie’s actual disappearance that lingers, but how familiar it feels in the men I have wanted in my own life. Maybe that’s why I can’t stop thinking about it—not just Connie, but the feeling of only ever catching the beginning of someone or something. You become attached to fragments: the way someone held eye contact, the mood of an evening, the version of yourself that briefly existed around them. 

To disappear is a kind of cruelty, but so is leaving someone suspended in almost-intimacy. There is at least a kind of honesty in leaving completely, a refusal to keep performing something that has already ended. That is why Converse continues to resonate. Not because disappearance is noble, but because modern love has made emotional unavailability feel normal.

New York is strange because loneliness arrives in crowds. You can be surrounded by motion and still feel untouched. So much of life here unfolds in interludes, through half-encounters. People leave, or simply stop arriving. Romances stall before they begin. Disappearance teaches us who we become in the absence of others, how often we long for the unavailable. 

I think about Connie in a way that feels a little made up, but only in the way all comforting things sometimes are. She’s floating in a lake somewhere in New Hampshire, the water still, her hair graying. She’s staring up at the sky, smoking a cigarette, laughing softly, as if she just remembered something she never needed to explain. In “Talkin’ Like You (Two Tall Mountains),” she sings about this place between two tall mountains called Lonesome. Everyone treats it like it means something heavy or symbolic, but she shrugs it off. When she’s there, she says, she’s not lonesome at all.   

Maybe nothing happened to Connie in the way we want there to have been something—a reveal, an explanation, a grand ending. Maybe she just went somewhere that didn’t require her to be anyone at all. Between the two tall mountains, in a place called Lonesome, where she isn't. 

I return to the songs and disappear into the quiet she left behind, away from the noise of the city, every boy problem. I drift from the archive of “almosts” waiting on my phone, from the questions that never find answers. 

I think Connie would have loathed Hinge. Lately, I’m beginning to understand why.