The romantic mixtape is timeless

Six years ago, when my now-husband was a friendly old flame from my high school days, I sent him an Apple Music playlist of my favorite songs at the moment. That wasn’t unusual: song swaps, album recommendations and musical superiority kept us in touch for almost a decade. Instead of a coffee date, it was, “Have you heard about Noname?” Instead of a long phone call, it was, “Have you heard the new GoldLink album?”

The last track on this playlist was “Saved” by R&B artist Khalid. “But I’ll save your number / Because I hope someday you’ll get the sanity to call me,” says the swooned chorus. “I hope you’ll say / You miss me like I miss you.” It was an innocent victim, 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 put it on the must-play list for our wedding.

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

Mixtape’s roots go back to the mid-to-late 1970s, with the advent of boom boxes and then the Walkman, writes Jehnie Burns, professor of history and cultural studies at Point Park University, in Mixtape Nostalgia: Culture, Memory and Representation. The Walkman, which dramatically shrunk the cassette player, spawned the first generation of teenagers who could drown out the outside world on the school bus or subway with headphones, and transformed music from a primarily social experience into an individual one. The ghetto blasters allowed ordinary people to make copies of albums – as well as radio and live music – on cheap tapes. Mixtapes made it possible for anyone to be an amateur DJ for the first time.

“Mixtapes were my way of making music, even though I could only play radio,” says Zack Taylor, a Brooklyn-based filmmaker and director of Cassette: A documentary mixtape, told me. By the mid-’80s, mixtapes were a tool for signaling identities and “a place for wordlessly sharing emotions,” as Burns writes. They were a new way of communicating for young people.

Of course, people started using this power to communicate with their crushes; after all, the romantic appeal is multifaceted. “For teenagers or people who don’t want to say, ‘I mean a lot to you,’ they can say that in a song,” Burns said. Peer pressure and conformity, braces and body hair—the clumsiness of puberty can leave a particularly large gap between how young people feel and express themselves. Crushing through song choices helps subtly and, crucially, plausibly deny the message. “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 searching for a potential partner. The mixtape can demonstrate both cultural cachet and a willingness to share that expertise with another person: introducing someone to Joy Crookes, Holy Hive, or Ciscero can be a gift in itself. It also allows the recipient to get to know you through what you like. Hi-Fi, Nick Hornby’s book-turned-movie-turned-TV-show is probably the best example of this idea. In the film, John Cusack plays the thrashing Rob Gordon, a heartbroken record store owner who uses his knowledge of music to communicate his love, condescend people and later make sense of his failed romances.

And while the mixtape is usually associated with a budding courtship, it works its magic in a different way for couples with long histories. For them, it can be a time capsule, says Regan Sommer McCoy, founder of archival project The Mixtape Museum. A mixtape can convey new emotions while reviving old memories: the catchy tune that played on the car radio at the end of a first date, the crowd favorite from prom in 1992, the Khalid song she sent you that made you think you were more than… just be friends

But not everything has made its way from audio tapes to mix CDs to today’s digital playlists. The experts I spoke to agreed that much of the beauty and romance of the original cassette mixtape lies in the linear experience. There is less skipping, deleting and mixing with tape. There are only the songs I chose for you in the order I chose them.

While listening to a personalized Spotify playlist isn’t exactly the same, the intimacy and intentionality of music curation still holds weight. Indeed, in the streaming age, the gift of a playlist solves a slightly different problem: it brings meaning to the flood of new releases and the blandness of algorithmic playlists. Curated playlists aren’t just background vibes; they are individual universes of coded flirting. A well-crafted mix playlist is still a confrontation: Hello you! I have a message! Sit down and listen!

If you’re going to be persuaded to deliver your own musical message for Valentine’s Day, there are a few basic rules. Have a topic first: 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 convey the message you intend. Also, choose a catchy playlist title – listen to an inside joke, point out the hidden message in the songs, write lyrics that best fit your topic.

Remember that song order is also important. Your opening number sets the tone and your last track is probably what you’ll remember most. And don’t forget the element of surprise – consider a balance between crowd pleasers and personally treasured gems. You don’t want the recipient to feel left out by the vagueness of your song choices, but you also don’t want to bore them by only providing the tracks they’re expecting.

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

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

“Can you tell where my head was when you found me? / Me and you went to hell and back just to find peace,” the song begins. “Man I thought I had it all I was lonely / Now you’re my life and soul I was lonely.” We also added this song to our wedding playlist.

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