New York City: When When Anticipation Isn’t Enough

Thoughts on Distance, Memory, and Emotional Boundaries

Hi, I’m Chase Roper, and I’m writing an essay about every They Might Be Giants song. If you like deep dives, nostalgia, or getting unreasonably emotional about music, subscribe below to read along for free. New posts arrive every week by email or in the Substack app.

Promotional CD for Factory Showroom (1996), the album that includes “New York City.”

Of all the songs on Factory Showroom, this one carries the most vivid memory for me.

Eleven Months Is Basically Married

Much of this album was listened to shortly after I got my driver’s license, during solo trips to my job or my girlfriend’s house. Caitlin and I were a couple for eleven months straight. In high school, eleven months was basically married. Near that eleven-month mark, I noticed a shift. Callbacks were delayed. She brought up one guy’s name with increasing frequency. I was the only one initiating connection. Caitlin seemed less engaged, less “future-focused,” calling me less, looking at me differently.

I’ve always been sensitive to shifts like that. This wasn’t subtle. Eventually, shortly after our eleven-month anniversary, she broke up with me.

I was glad to hear from you ‘cause I was all alone

I thought that if I could make a grand gesture, something symbolic and deeply personal, she’d remember how much she meant to me and want to come back.

I filled a soft felt pouch with saved movie tickets, pictures of us, and a poem I’d written. It just needed one last thing: a cassette tape of me singing a song for her and playing the guitar.

I chose New York City.

You called me last night on the telephone

And I was glad to hear from you ‘cause I was all alone

You said, “It’s snowing, it’s snowing! God, I hate this weather!”

Now I walk through blizzards just to get us back together

A Cover That Means It

New York City is a cover¹, but it doesn’t feel like one. It feels more like an adoption.

John Flansburgh originally planned to record the song with his side project, Mono Puff, which makes sense. It’s a little cleaner, a little more straightforward than most mainline They Might Be Giants tracks. What drew him to it wasn’t irony or cleverness, but sincerity. The song is openly tender, like a love letter that isn’t written from a strictly gendered point of view.

Flansburgh has said that part of what excited him about covering it was hearing that vulnerability come from a man’s voice. The song was written by women, and he’s admitted that he doesn’t think he could write something this emotionally direct himself. Covering it was a way of borrowing a kind of emotional honesty he admired but didn’t feel equipped to write on his own.

Three Days Away

A key element of this song isn’t just that two people are separated by distance, or that the singer clearly has deep feelings for the person on the other end. It’s about anticipation. The specific, electric kind that comes from knowing a visit is no longer hypothetical. Being next to that person isn’t some vague future idea; it’s a matter of days.

Handwritten letters, DMs, and phone calls are powerful ways to stay in each other’s orbit. To remain attached. But sharing space - being in the same room, laughing at the same moment, talking without delay - is a completely different feeling. In some ways, those other forms of connection might even feel more intense because of the distance. But the singer in this song knows something important: he’s only three days away from arriving in the city where this person lives, and he can hardly wait.

Knowing Someone From Far Away

There have been many points in my life when I’ve related to the feelings expressed in this song. What I didn’t fully appreciate until recently is how different a relationship feels when distance isn’t just an inconvenience, but a defining feature. Even when it isn’t romantic. Especially when it isn’t clearly defined.

Having someone you talk to about everything. Someone you let into your inner life. A person you think about throughout your day. When something funny, terrible, or gossip-worthy happens and your first thought is, Oh man, I can’t wait to tell them this. If that person lived within five miles of you, you’d be meeting up constantly. Grabbing food, sitting around, watching junk TV, sitting at a bar until it got late without noticing. But you can’t do that when there’s a plane trip or an eight-hour drive between you.

I don’t write these essays to explain songs as much as to sit with the feelings they stir up. If that’s your kind of thing, you can subscribe for free and read along each week.

I Have a Person Like This

I have a person like this.

Someone who fits every description above. Someone I talk to about everything. Someone whose voice has become so familiar, long before their physical presence ever could. Sometimes, this kind of closeness can feel like momentum. Like something quietly building toward an arrival.

In New York City, there’s a clear dating, in-love energy at play, and that isn’t exactly what is happening here. But the sentiment lands anyway. The anticipation. The sense that distance is temporary. That the closeness is just waiting for the logistics to catch up.

Even though the anticipation can feel like movement that connection, by itself, doesn’t guarantee a direction. And wanting something carefully doesn’t make it any more emotionally safe if the wanting isn’t mutual.

That doesn’t make the feeling foolish. It just means that I’m learning how to pace things differently in my life. And it feels nice.

That Cassette Didn’t Fix Anything

Caitlin and I met in the parking lot of the grocery store where she worked after her shift. We sat in my car and I gave her my gift. I even played the cassette for her. She didn’t fall in love with me all over again, and we didn’t get a perfect rom-com ending to our story.

As much as I love this song, New York City carried a lingering sense of embarrassment for years, tethered to those memories. Today, I have a new appreciation for high-school Chase. There’s nothing wrong or embarrassing about loving someone, or being vulnerable, or saying how you feel. For better and worse, I feel things deeply and intensely. I’m just learning now how to do that with a little more care, and a little more protection for myself and for the people I feel things toward.

Anyway

The older I get, the more I realize that New York City isn’t really about a place, or even about romance. It’s about believing that closeness is possible again. About counting days. And about knowing how to carefully honor that excitement.

---

You’re reading one of my Factory Showroom essays — an album full of oddball beauty, quiet heartbreak, and some of the band’s most elegant songwriting. Writing through this era has felt like excavating older memories with sharper tools.

See all Factory Showroom posts

Start Here

Dive deeper into TMBG lore at TMBW.net (fan-run and fantastic)

1. Original New York City, Cub circa 1995