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Shake it off: What happened when a lovelorn Tatler staffer emulated Taylor Swift’s sorrowful progress around London?

Oct 7, 2025
4 min read
Taylor Swift
Taylor Swift

Taylor Swift and I have something in common. No, it’s not $1.1 billion in the bank, sadly. But, like Taylor, I have recently lost my London Boy.


‘You’re so lucky,’ a friend tells me one rainy morning. Confused, I ask why. ‘You get to go through a break-up just as Taylor Swift drops a new album,’ she says. Lucky? Unlike the pop megastar, who’s earned millions making music out of her love life, I don’t have a private jet in which to sob. Or a recently single A-lister bestie like Sophie Turner to paint the town red with. But, as I drown my sorrows listening to The Tortured Poets Department – one heart-wrenching ballad after another – I start to wonder: could I turn a crisis into an opportunity?


I can certainly retrace the singer’s footsteps in London, sporting a freshly trimmed Taylor-esque fringe. My rationale? I am seeking the tortured poet within me, so that I too can turn my tears into art – and maybe even end up with a Swift-sized cheque afterwards. That’ll teach London Boy.



I begin at The Black Dog pub in Vauxhall: the scene of the crime in the now-infamous song in which Taylor croons: ‘And your location/You forgot to turn it off/And so I watch as you walk/Into some bar called The Black Dog.’ As I sip a Guinness, I wonder which table Joe Alwyn might have been sitting at when Taylor tracked him down on Find My iPhone. At my table for one, I start brooding about my ex – then, suddenly, I have an epiphany: I can make my London Boy jealous. There is a handsome man working behind the bar. He compliments my fringe. Did he just wink at me?



But my mission is l’art, so I need to get writing. In my Gen Z ‘tortured poet’ get-up – a short, preppy black skirt, Ralph Lauren shirt and cashmere jumper – I head to the National Portrait Gallery. What better way for a heartbroken writer to spend her morning than seeking inspiration from the Romantic poets? Stern paintings of Byron, Wordsworth and Coleridge glare down at me (my skirt is rather risqué by Victorian standards) and Swift’s album Folklore echoes in my mind: ‘Take me to the lakes where all the poets went to die,’ she sings on one track. Drama like this is well-canonised. Perhaps I should fling myself into the Thames?




Inspiration is eluding me. It’s time for a change of scene – and what do all poets have in common? A visceral love of nature. I head to Hampstead Heath, which happens to be Taylor’s old stomping ground. (In the song ‘So Long, London’, over a catchy hook, she chimes: ‘I left all I knew, you left me at the house by the Heath.’) I sit and look out onto the grassy paradise, waiting for creativity to strike – some angsty lines that might perfectly articulate the heartbreak that made Taylor her fortune. But a pigeon comes to peck at my trainers as I try to rhyme ‘loss’ with ‘girlboss’.


I need a creative pick-me-up. The Romantics favoured opium, but I settle for a Tennessee whisky (Taylor’s order): Jack Daniel’s on the rocks. I am at The Flask in Highgate, a Georgian inn with a cosy interior and a social clientele. Taylor and Alwyn were once photographed here after dining on haddock and chips in the back. I order the same, but a lonely fish and chips doesn’t exactly scream ‘eligible bachelorette’.



Post-whisky, I am finally feeling woefully, romantically pensive, and I skulk off to the home of the original tortured poet, Keats: a beautiful whitewashed Regency house in Hampstead. I read Ode to a Nightingale in the melancholic writer’s sitting room and listen to Taylor’s ‘I Can Do It With a Broken Heart’. I suddenly become overwhelmed with memories. I miss my London Boy. But my words don’t come. ‘Keats/Beats/Meets/Feats…’ I mooch onwards.




Then I pass the Kentish Delight kebab shop in Kentish Town, where Taylor once filmed a music video and bought all 45 crew members a kebab each. It’s also where she used to devour chicken pittas with Alwyn. In fact, proudly pinned in the shop window is a picture of Taylor with the owner. They tell me she’s coming back in June to film another music video – and, according to the owner, ‘for 45 more orders!’ I open the Notes app on my phone: ‘Me and you eating chicken shawarma/How will I ever find another?’ I type. It’s no Grammy-winning epic.




It turns out being a tortured poet is no easy feat. I’m no closer to my first million or a new beau such as Travis Kelce, and the kebab man is waiting for business. Lonely as Wordsworth’s cloud, I text a friend, suggesting martinis. ‘Where?’ she says. ‘I’m feeling The Twenty Two?’ ‘Poetic,’ she replies. If only. Then, divine inspiration strikes, and I note it down: ‘We are never, ever, ever getting back together.’ Gold dust! Or have I heard this somewhere before?


 
 
 

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