The Enduring Romance of Mixtapes

Why song curation is a love language

Two musical notes as beating hearts
Ben Hickey

Six years ago, when my now-husband was still just a friendly old flame from my high-school days, I sent him an Apple Music playlist of my favorite songs of the moment. This was not unusual: Song swapping, album recommendations, and musical one-upmanship had kept us in touch for nearly a decade. Instead of a coffee date, it was “Have you heard of Noname?” In lieu of a lengthy phone call, it was “Listened to the new GoldLink album yet?”

On this playlist, the final track was “Saved” by the R&B artist Khalid. “But I’ll keep your number saved / ’Cause I hope one day you’ll get the sense to call me,” goes the swoony chorus. “I’m hoping that you’ll say / You’re missing me the way I’m missing you.” It was an innocent offering, I swear! But for my now-husband, it was an opening. “That song told me there was a chance,” he told me years later. In 2022, we added it to the must-play list at our wedding.

All of this is to say: The gift of music curation is powerful, a love language to be wielded with care. In fact, the courtship method that I gratefully stumbled into has persisted for decades. True, not many romantic mixtapes these days are actual tapes—you’re more likely to receive a Spotify playlist with a flirtatious title than a cassette with Sharpie cover art. But the essential elements remain: a compilation of songs, thoughtfully selected and precisely ordered, that intimately express to the recipient, “I see you.” Or perhaps, “I want you to see me.”

The roots of the mixtape go back to the mid-to-late 1970s with the arrival of the boom box and then the Walkman, writes Jehnie Burns, a history and cultural-studies professor at Point Park University, in Mixtape Nostalgia: Culture, Memory, and Representation. The Walkman, which shrank the cassette player dramatically, gave rise to the first generation of teens who could drown out the outside world on the school bus or subway via headphones, and it transformed music from a primarily social experience into an individual one. The boom box allowed regular people to make copies of albums—as well as record the radio and live music—on cheap tapes. For the first time, through mixtapes, anyone could be an amateur DJ.

“Mixtapes were my way of participating in music, even though I could only play a radio,” Zack Taylor, a Brooklyn-based filmmaker and the director of Cassette: A Documentary Mixtape, told me. By the mid-’80s, mixtapes were a tool for identity signaling and “a venue for sharing emotionality wordlessly,” as Burns writes. They were a new way for young people to communicate.

Naturally, people started using that power to communicate with their crushes; the romantic appeal, after all, is manifold. “For teenagers or people who don’t want to say, ‘You mean a lot to me,’ they can say that in a song,” Burns told me. Peer pressure and fitting in and braces and body hair—the awkwardness of puberty can leave a particularly wide gap between young people’s emotions and their ability to express them. Telegraphing a crush through song choice helps deliver the message with subtlety and, crucially, plausible deniability. “There’s a safety in a mixtape, where you can hide behind the song,” Taylor said. Love letters require direct authorship, and jewelry is an expensive gamble, but music curation is cheap and mysterious.

Then there’s the bonus of peacocking for a potential mate. The mixtape might demonstrate both cultural cachet and a willingness to share this expertise with another person: To introduce someone to Joy Crookes or Holy Hive or Ciscero can be a gift in itself. It also allows the recipient to get to know you through what you like. High Fidelity, the Nick Hornby book turned film turned TV show, is probably the best example of this idea. In the movie, John Cusack plays the flailing Rob Gordon, a heartbroken record-store owner who uses his knowledge of music to communicate his love, condescend to people, and, later, understand his failed romances.

And although the mixtape is typically associated with a budding courtship, it works its magic in a different way for couples with a long history. For them, it can be a time capsule, says Regan Sommer McCoy, the founder of the archive project The Mixtape Museum. A mixtape can communicate new emotions while spurring old memories: the earworm that played on the car radio at the end of a first date, the crowd favorite from prom 1992, the Khalid song she sent you that made you believe you could be more than just friends.

Yet not everything has carried over from tapes to mix CDs to the digital playlists of the present. The experts I spoke with agreed that much of the beauty and romance of the original cassette mixtape lies in the linear experience. There is less skipping, deleting, and shuffling with tape. There are only The Songs I Chose For You In The Order In Which I Chose Them.

Although listening to a personalized Spotify playlist isn’t exactly the same, the intimacy and intentionality of music curation still hold weight. In fact, in the streaming era, the gift of a playlist addresses a slightly different problem: It brings meaning to the flood of new releases and the blandness of algorithmic playlists. Curated playlists are not mere background vibes; they are individual universes of coded flirtation. A well-made mix playlist is still a confrontation: Hey, you! I’ve got a message! Sit down and listen!

If you’ve now been persuaded to deliver a musical message of your own for Valentine’s Day, there are a few basic rules. (If you need an example playlist, here's one I made on Spotify to accompany this article.) First, have a theme: Is this a walk down memory lane? An invitation to get to know the “real” you? You can expect the recipient to pay close attention to the lyrics, so make sure they’re conveying the message you intend. Also, have a catchy playlist title—harken back to an inside joke, hint at the hidden message in the songs, crib a lyric that speaks best to your theme.

Keep in mind that song order matters too. Your opening number sets the tone, and your final track is likely what they’ll remember most. And don’t forget the element of surprise—consider a balance of crowd pleasers and personally cherished gems. You don’t want the recipient to feel boxed out by the obscurity of your song choices, but you also don’t want to bore them by delivering only the expected tracks.

Above all, any romantic gift should be vulnerable. Done well, a mixtape is a chance to be bold, to show your cards. “Music itself is not safe,” Taylor said. “So a mixtape shouldn’t be either.”

Four years ago, my now-husband traveled from Chicago to Washington, D.C., to pay me a supposedly platonic visit. We spent 48 hours talking, teasing, song swapping, and exchanging long, meaningful looks. Then we shared a very awkward goodbye. Neither of us knew how to make the next move. A few days later, I sent him another playlist. This time, I knew what I was doing. It opened with “Hell N Back,” by the indie-rock artist Bakar—an unsubtle declaration. Underneath the song’s bright, whistled opening and sunny ska-like horns was a straightforward message: Let’s do this thing for real.

“Could you tell where my head was at when you found me? / Me and you went to hell and back just to find peace,” the song begins. “Man, I thought I had everything, I was lonely / Now you’re my everything, I was lonely.” We added that song to our wedding playlist too.

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