I am trying to break your heart

on digital decay, grief, playlists, and Wilco

Grief is a funny and fickle thing. You can be busy living your life, minding your own business, and then one day be upended by an unexpected and random thing.

For me, it was the recent news story that Google was planning to start deleting accounts that hadn’t been used in more than two years “to help avoid security risks,” NPR reported.

After first securing my own accounts, the next thing I thought of was my beloved friend Nikki Delamotte, gone five years this year. Has her Google account been accessed in that timeframe? I have no idea.

Nikki was my night buddy on Gchat. I’d be up late working or fretting over a deadline and, inevitably, she would be too. We’d talk and gripe, gossip and giggle—all virtually, of course—with the ping of an instant message trilling away in the background. The memes, links, idle chatter, confessions, serious stuff—all mixed together, no batch of zeroes and ones more important than another.

Our Gchat thread was a years-long conversation that abruptly stopped, punctuated at the end by a message I sent to her that awful morning, asking if she was there—even though in my heart I already knew she wasn’t going to answer. I messaged our thread again a few days later with a small note I once again knew was going into the void, because I couldn’t bear to have the last exchange be that fake-cheery check-in.

With the Google news, does that mean our conversations are going to disappear? Our thread (and her avatar) is still permanently in my Gchat column. I worry that one day I’ll wake up and she’ll be gone again.

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Beyond all this, I felt unmoored by the mere idea that yet another part of Nikki’s digital presence might disappear.

A few days after her murder, her Facebook page switched into “Remembering” mode before any of us could access it. The inaccessibility was at odds with her social habits. She would RSVP to countless Facebook events, both seriously and in jest, because she loved being supportive; in fact, I know she happily RSVPd to an eclipse event happening in 2024 before she died.

To add insult to injury, the pre-El*n M*sk Twitter unfollowed her entire list of followers and dismantled a thread of stories she carefully curated, work of which she was exceedingly proud. Today, these links show up as unavailable, permanent scars of digital decay. I was irate on her behalf when I noticed all of this.

At a later point, I bought more Google storage so I could still access our text messages, after a moment of panic when it seemed like our conversations might have evaporated in the cloud. If I ever wanted to revisit our texts, I wanted to know they were there waiting for me.

Until Nikki died, I didn’t realize our communication was so ephemeral.  Call it willful ignorance: I’ve been Extremely Online for a quarter-century now and should know better that nothing is forever online, given how much of my own internet history is just gone.

But our texts, chats and DMs felt like irrefutable and tangible proof of our friendship and our bond. They never seemed like they’d just vanish.

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I can’t listen to the playlist we made for Nikki’s memorial, as it’s still too painful. Bonded by grief, a group of us labored for hours over what songs to play and in what order. It was deeply important that we sent Nikki off with the right mix—the perfect mix—that covered her favorite songs and moods. We combed over the lyrics making sure the songs didn’t have terrible references; I audio-edited one favorite song of hers that had lyrics alluding to a gun.

But Nikki herself was a habitual playlist-maker, and I turned to these after she died. She had her favorite artists—her recently played feature had the Wrens and Drive-By Truckers—and preferred styles. There’s lots of morose, acoustic indie-folk—fitting, since one of our last conversations we talked about the saddest Death Cab for Cutie songs—and popular indie rock from certain eras that’s frozen in time. Nikki also had her singular song obsessions. The year she died, she was into Kacey Musgraves’ dewy “Slow Burn,” a song with striking lyrical parallels to her own life.

Listening to playlists can sometimes feel a little invasive. Making a playlist for yourself is an intimate act—your true musical id, ego and superego coming through. Some of Nikki’s playlists had specific dates; others simply had the month, making the timeframe fuzzy. It was hard to say whether these were all favorites, or little sonic reminders to herself. But I still listen to them, and I still find their existence deeply comforting, as they’re relics of her vibrant emotional life.

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The playlist of Nikki’s favorite music especially hits me. It’s not a long list, but it’s substantial—Big Star, Stevie Wonder, Sam Cooke. The ELO song we did play at her memorial service. R.E.M.’s dark and stormy “Country Feedback,” an absolutely brilliant song that transformed into something else entirely for me after Nikki died.

One of the other songs on her favorites list is Wilco’s “I Am Trying to Break Your Heart.” That’s one of my favorite Wilco songs too; frankly, it takes my breath away every time I hear it.

At nearly seven minutes long, it’s a leisurely example of pure sonic deconstruction. The initial tranquil humming keyboards and steady rhythms suddenly break into arrhythmia and go out of step, out of phase—a slow-motion collapse in the guise of disintegrating piano, tangled drums, percussion shards.

As “I Am Trying to Break Your Heart” marches forward, things stabilize: The piano keeps a stiff upper lip, the rhythms feel more regular. But that’s only because of resignation; it feels certain that there won’t be a good ending.

To me, the song also sounds like a funeral. Jeff Tweedy is a droll protagonist, narrating his own emotional and romantic collapse with eerie calmness. But by the end, his voice starts to disintegrate and grows faint, as if he’s peeling off from the song to go elsewhere or maybe ascending heavenward to another plane. Fittingly, the last verse describes someone trying to disappear into their anguished grief:

Disposable Dixie-cup drinking
I assassin down the avenue
I'm hiding out in the big city blinking
What was I thinking when I let go of you?

After this moment, the song starts to fray for the final time, with dull background static providing a backdrop for a droning keyboard and pockmarked sounds. It’s not necessarily sad, just wistful, on a slow, fuzzed-out march to the inevitable.

I thought of Nikki and her own impossibly short life journey, and wish that “I Am Trying to Break Your Heart” didn’t feel so on the nose.