Personalised playlists have become the latest weapon in our online dating war | Elle Hunt

The way culture works today, you will either know everything there is to know about West Elm Caleb or nothing. For the uninitiated, he is a 20-something New Yorker who works at a furniture store and gained online infamy for his poor dating behaviour. A group of women who had met Caleb via dating apps and then connected with each other on TikTok have accused him of ignoring messages, recycling lines, sleeping with one shortly before going on a date with another and sending unsolicited nudes.

After 15m views of the #westelmcaleb hashtag on TikTok, the facts of the situation are unclear and the ethics murkier still. I do, however, feel qualified to comment on one element: Caleb’s seduction playlist on Spotify. One of the claims against Caleb was that he sent at least two women the same playlist, each believing it to have been personalised; it’s now being circulated to inform our collective arbitration of his conduct.

It is testament to the romantic power of music that this has been singled out as a transgression. It also demonstrates how, on dating apps, music taste has become one of the primary ways of signalling one’s suitability as a mate – and how, by reducing people to profiles of their likes and dislikes, this taste has been weaponised.

The West Elm Caleb saga coincides with a competition from the dating app Bumble asking users to send a bespoke mixtape to a match, based on its survey that found that 59% of people believe music to be the most romantic way of expressing their feelings. Another survey last year by OkCupid found that there were almost 5m mentions of music on users’ dating profiles; 37% of daters surveyed said they would prefer their partner to be into music over movies, books or sports. A new dating app, POM (Power of Music), goes one further, claiming to pair users on the basis of their listening history.

My own 15 years of dating can be sequenced into mix CDs and playlists, given and received; “exchanging favourite songs” registers between first and second base. Without music, I may not have ever had sex. As such I delved into Caleb’s tried-and-true playlist with interest – and trepidation. Would I fall for him, too?

No. It’s obvious from track three that this guy is trouble. Mazzy Pop’s best-known song by far, Fade Into You, is too obvious to be indicative of taste – and it’s too declarative of intention (“I want to hold the hand inside you”) to belong on Side A.

It makes the case for Caleb as a common or garden “softboi”: the earnest young men on dating apps labouring to define themselves by their performed sensitivity and superior taste. (See the @beam_me_up_softboi account on Instagram, which documents the crude attempts at seduction or manipulation by men who believe themselves to be cultural iconoclasts for liking “alternative” music – like that little-known outfit Tame Impala.)

Caleb’s playlist does include the softboi staples the Smiths, Ariel Pink and King Krule – but also more women and non-white, non-western musicians than one might expect of a dudebro out to maximise matches. This could equally mark Caleb out as somewhat attuned to racial and gender politics, or simply better at throwing his dates off the scent – testament to the funhouse mirror of modern dating.

If we read too much into music taste, it’s probably because it is one of only a handful of data points we’re given to assess potential romantic compatibility. In the past, “Beatles or Stones?” and “Oasis v Blur” were icebreakers that you’d quickly move past if you fancied each other enough; on dating apps, they are the precursor to a conversation occurring at all.

It brings to mind High Fidelity, specifically its protagonist’s dating dictum that “what really matters is what you like, not what you are like”; his eventual admission that it’s the other way round reflects an eventual maturity. Today dating apps conflate the two. OkCupid’s survey found that one in three singles believe musical preference to be a good indicator of intelligence.

No wonder Caleb opted to hedge his bets. The overall impression from his playlist is of warm guitar tones and soulful vocalists: it communicates accessible, Pitchfork-friendly cool without saying much about sender or receiver, let alone who they are to each other. I showed it to my friend. “Wait,” she said, horror mounting, “I’ve dated this man.” (We checked; she hadn’t.)

That pervasive universality speaks to the challenges of making a truly personalised playlist. There were unsettling similarities between Caleb’s and ones I’ve sent to love interests myself. Him: the Mark Ronson remix of Angel Olsen’s New Love Cassette, and the Magnetic Fields’ The Book of Love from 69 Love Songs. Me: the Chromeo remix of Green Light by Lorde, and the Magnetic Fields’ A Chicken With Its Head Cut Off from 69 Love Songs (“Eligible, not too stupid …”). I have even got in trouble for repurposing songs for new love interests. If you aren’t dating Caleb, it seems, you may be Caleb.

But if it was as hard to make an original, effective mixtape as High Fidelity made out 27 years ago, it’s even harder now. Not only are you unconstrained by the runtime of a cassette or CD, you can pick from a library containing nearly every love song ever recorded – no wonder we end up picking from the same 69.

Making a mixtape was “like writing a letter”, said High Fidelity’s Rob. Today creating a playlist can be like a social media status update: intended for an audience that is ambiguously defined and readily repurposed. Even those made with care and treasured as reminders of past relationships feel risky to revisit in such a connected ecosystem – I tend to switch to private listening, lest I be perceived from the “friend activity” panel to still be carrying a torch.

If that sounds paranoid, one friend recently discovered that an ex-boyfriend was still adding to a playlist he had sent her, nearly six months after their last contact. (A recent addition: Jon Brion’s theme for Eternal Sunshine of the Spotless Mind.)

A mixtape’s lasting romantic charge came from the investment of time, the thought put into the sentiment: it was emotion trapped in amber. A playlist, however heartfelt, feels impermanent and less potent.

As I wrote recently of Spotify’s personalised end-of-year roundup Wrapped, the fact that something as uncomplicated as bonding over music can be made so unsatisfying should be considered a platform failure. Indeed, algorithmic playlists (and the Spotify-friendly pop songs that open with the chorus) break Rob’s first mixtape rule: don’t give your listener what they want straight away – you remove the incentive to work for the good stuff.

There are parallels here between streaming services and online dating. It’s no wonder that Caleb seems to have had such success operating at the intersection of both, pairing app-matches with playlists: they allow for endless easy introductions at the expense of serendipity and investment. See how POM, “the dating app for music lovers”, describes its approach to matchmaking: connecting users “based on their music history and emotional responses … to curate a perfect end-to-end dating and social experience”. Be still, my beating heart.

I thought I’d found my own perfect music-history match on OkCupid the other day. He was wearing a Randy Newman T-shirt in his profile picture. I have a Randy Newman print framed in my hallway. Obviously, we were said to be 92% compatible.

I got overexcited and sent him several messages in quick succession about Randy Newman, some in all caps. (“IS THAT RANDY NEWAMN?”) I assumed he would be excited as well, given that there are estimated to be around only 40,000 devoted fans of Randy Newman and most are middle-aged men.

He never replied. I sent another message: “I cannot believe you would leave a Randy Newman fan with whom you are 92% compatible on read. What are your other messages like!!!” I was going for outrageous, alarming, courageous, charming. I may have just come across mad.

But I like to think that, had we met at a bar or through a friend, we might have flirtily debated Good Old Boys versus Sail Away. Eventually I’d have shown him the print in my hallway; we might have played Love Story (You and Me) at our wedding as an excellent in-joke. As it is, we never made it past track one, side one.


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