Note: This short reflection began simply as a reaction to hearing “Sixers” from The Price of Progress by The Hold Steady. Over time, however, it became clear that the song belongs to a larger lineage in Craig Finn’s writing: the quiet, observant songs about adult relationships that never quite come together.

Listeners familiar with Finn’s work will recognize echoes of earlier pieces such as “Spinners,” “Tangletown,” “Esther,” and especially “Jessamine,” where a brief encounter carries emotional weight far beyond its duration. What interests me most about these songs is not romance itself but the fragile moment where two people briefly imagine a connection that may or may not exist.

“Sixers” captures that moment with remarkable economy. Like many of Finn’s best narratives, the drama unfolds not through big revelations but through small gestures, passing observations, and the social physics of an evening that slowly runs out of momentum.

The song feels unmistakably rooted in the atmosphere of the pandemic and its aftermath—a period when many people were cautiously trying to reconnect with the world after long stretches of isolation. In that sense the characters in “Sixers” are not unusual figures but recognizable ones: two lonely people improvising a small pocket of companionship inside a quiet apartment building.

That the connection ultimately proves fleeting is not really the point. The attempt itself—the knock on the door, the drinks, the conversation—is what gives the evening its meaning.

I came to The Hold Steady a little late. Around 2016 I first heard “Constructive Summer” and “Sequestered in Memphis” from the 2008 album Stay Positive—probably through the Spotify algorithm, which occasionally earns its keep. That was the gateway. Even though I had missed the band’s original wave of excitement, I quickly made up for lost time and worked my way through the entire catalog.

A couple years later I went deeper and began listening seriously to the solo records by Craig Finn. That opened another rabbit hole. My early favorite was “Three Drinks,” but over time songs like “A Bathtub in the Kitchen” and “It’s Never Been a Fair Fight” began to feel like the real center of gravity in Finn’s songwriting. The solo records are quieter and more novelistic than the Hold Steady albums, and in some ways I’ve come to think they are even stronger.

Around that same time a music-obsessed friend I met at two Hold Steady shows at Brooklyn Bowl told me that if I really wanted to understand Finn’s writing I needed to go back further, to his earlier band Lifter Puller. He was right. Lifter Puller turned out to be a wilder and more manic version of the same storytelling instinct. The songs move faster, the rhymes pile up in breathless clusters, and the characters—people like Nightclub Dwight—feel sketchier and stranger than the ones who would later populate Hold Steady songs about figures like Charlemagne. Tracks like “Nice Nice” and the closing songs on Fiasco are still some of the most exhilarating music Finn ever made.

All of which is to say that Craig Finn has gradually become, for me, the greatest living songwriter—even if I still concede that the all-time crown belongs to Bob Dylan.

What makes Finn particularly fascinating is the emotional terrain he covers. Early Hold Steady songs often dealt with youthful chaos—parties, drugs, Catholic guilt, and the reckless mythology of young adulthood. But over time he has developed another genre that may be even more compelling: songs about messy adult relationships.

These songs usually revolve around people chasing the thrill of a connection even when they suspect, somewhere deep down, that the connection will probably be short-lived. The crush, the fling, the brief dalliance—these impulses are deeply wired into human psychology and deeply embedded in the culture and art we consume. Finn understands that instinct perfectly. His characters repeatedly pursue moments of intimacy that are intense, fleeting, and often slightly ill-advised.

You can hear that theme in songs like Spinners, Tangletown, Esther, and perhaps most perfectly Jessamine. What distinguishes Finn’s writing is the concision with which he captures these emotional situations. Few songwriters are better at compressing an entire relationship dynamic into a handful of lines. In that respect “Jessamine” may be his masterpiece: a small, perfectly observed sketch of longing, timing, and missed possibility.

It is within that lineage that the song “Sixers,” from the 2023 album The Price of Progress, finds its place.

The Price of Progress feels unmistakably like The Hold Steady’s COVID-era record. Finn has described the album as a set of narrative songs about people trying to survive modern life—navigating isolation, economic pressure, technological dependence, and the strange psychological residue of the pandemic years. While the previous album Open Door Policyhad largely been completed before the lockdowns, The Price of Progress was written in the wake of that disrupted period when people were cautiously trying to rebuild their social lives.

“Sixers” captures that atmosphere perfectly.

The entire story unfolds inside an apartment building where two strangers live stacked one above the other. Both are alone. Both are restless. Both are coping with their evenings through small chemical adjustments—beer, pills, and cocktails.

The woman downstairs begins the night with a six-pack from the store down the street and a prescription meant to help her focus her attention. The man upstairs has just returned from another steakhouse dinner with coworkers in asset management, a job that is, as Finn notes dryly, “as thrilling as you’d think.” The two have seen each other before at the mailbox, one of those semi-public urban spaces where strangers develop a faint familiarity without ever truly knowing each other.

The encounter begins with a pretext. She knocks on his door and tells him she thought she heard footsteps upstairs.

The truth, of course, is that she is simply lonely.

Like many Finn songs, the story unfolds in the semi-public spaces of urban life—apartment hallways, mailboxes, shared walls—places where strangers gradually become aware of each other without ever becoming fully connected. Finn has always had the instincts of an urban anthropologist, observing the small rituals and awkward encounters that define city living.

For a while the evening works. They talk about work and school. They discuss how the city has changed. They make drinks in the kitchen—he measures gin while she crushes pills on the counter. At one point he is “muddling the mint,” a beautifully precise detail that captures the strange domestic intimacy that can arise between two people who barely know each other. Soon they are dancing, sending out for takeout, and even sharing inside jokes.

For a few hours the night begins to resemble a small, improvised relationship.

And then comes the hinge of the entire song.

Sunrise into sundown, sending out for takeout, sharing inside jokes now
He finally tries to kiss her and she says that it’s not like that.

With that single line the entire evening collapses.

Everything that seemed like romantic chemistry turns out to have been a misread signal. The connection was real enough to sustain conversation, drinks, dancing, and jokes, but not the kind of connection he thought it was.

One of Finn’s recurring themes is the almost-relationship—encounters where two people briefly imagine a connection that never quite materializes. Songs like Jessamine, Spinners, and Tangletown inhabit that fragile territory. “Sixers” belongs squarely in that tradition.

Finn doesn’t dramatize the moment with an argument or confession. Instead he shows the social physics of awkwardness taking over: everything slows, the conversation falters, and the energy drains from the room.

The next gesture is even more telling.

She cleans off the countertop and says she should probably go.

It is a tiny domestic act, but it carries enormous emotional weight. Cleaning the counter becomes a way of resetting the scene, erasing the traces of the evening before leaving.

Like many Finn songs, “Sixers” tells its story through objects as much as through dialogue. The room fills with small details: the six-pack from the corner store, the pill bottle in the cupboard, the carefully mixed drinks, Sinatra on the stereo, and one quietly devastating observation about the apartment’s décor.

At one point she notices a Nagel poster hanging on the wall in a silver frame and thinks it looks kind of lame.

It’s a perfect Finn detail. In a single line we learn something about the guy’s taste, his slightly square professional aesthetic, and the quiet judgment forming in her mind even while the evening unfolds.

Months later she sees him again in the hallway. This time he is standing with his fiancée, whose name she can’t quite remember—Kelly or Katie.

The moment closes the loop of the story. Whatever possibility once existed between them has long since evaporated. The evening that once felt full of potential turns out to have been only a brief improvisation between two lonely people passing through the same building.

The song ends where it began, with footsteps.

But this time the sound isn’t real.

She thinks she hears footsteps
But now they’re not really there.

The knock on the door that began the story was an attempt at connection. The footsteps at the end are only the ghost of that attempt, echoing in the quiet of her apartment.

Like many of Finn’s best songs about adult relationships, “Sixers” isn’t about catastrophe. Nothing explodes. No one storms out. The drama is smaller and more recognizable than that.

It is simply about lonely people improvising connection in a time of trouble.

And sometimes getting it slightly wrong.

Note: If you like this essay, you may also like the essays below which also deal with the singer-songwriter Craig Finn and his band The Hold Steady.