Why Taylor Swift’s break-ups mean big business
Love is a mystery. Through what obscure and mystical alchemy two people fall for each other is a conundrum that has perplexed everyone who has ever fallen under love’s spell. Is it their eyes? Their scent? Their endearing lack of pretension? Or is it their propensity to inspire heartfelt lyrics that can be turned into songs that can then be turned into platinum-selling albums, that can be turned into global tours that will make you the second-richest self-made woman in the music industry?
Jesus might have turned water into wine, but Taylor Swift has turned break-ups into bucks, a process no less miraculous, and almost as biblical. The 33-year-old singer has enjoyed a string of starry romances, and throughout her career has peppered her songs with references and coded hints. The result is that each new release inspires a multitude of articles and theories speculating about who and what she’s singing about.
So successful is the songwriting formula that it has amassed her a net worth of $740 million, according to Forbes, a sum that surpasses both Madonna and Beyoncé. Her detractors might say that this has come at a cost (her critics joke that no man wants to date her because they’re terrified details of their relationship will end up in a song), but Taylor is unlikely to care. She’s singing all the way to the bank.
Her latest relationship, with 1975 frontman Matty Healy, has reportedly hit the buffers – in the same week she confirmed the re-release of her Speak Now album, and continues her global Eras tour. Here we trace the history of her most significant relationships, and examine which ones have most influenced her songwriting.
Joe Jonas
July – Oct 2008
Some break-ups are long and drawn out. Others end in a 25-second phone call. The latter was Taylor’s fate, after the singer Joe Jonas of the Jonas Brothers dumped her after falling for actress Camilla Belle. Jonas inspired the title track of her 2008 album, Fearless, a fact that he was surprisingly sanguine about, saying in a 2015 interview that when you date a musician, having a song written about you “goes with the territory”.
It certainly does: Jonas supposedly inspired several more songs, including Last Kiss and Better Than Revenge on the 2010 album, Speak Now, the latter including the lyrics “You might have him/But I’ll always get the last word”. Oof.
But Taylor still wasn’t done. Re-recording the Fearless album in 2021, she dropped two vault songs, Mr Perfectly Fine and You All Over Me – both about Joe.
Taylor Lautner
Aug – Nov 2009
They may have met on a romcom called Valentine’s Day, but no amount of hearts, flowers and matching names could keep these two together, and they split in 2009. Back to December, on 2010’s Speak Now, was inspired by him, and holds the distinction of being her first song to contain an apology. “This is a song full of words that I would say to him, that he deserves to hear,” she said at the time, adding that it was “about a person who was incredible to me – just perfect”.
John Mayer
Nov 09 – Feb 10
“Mayer The Player”, the singer who also dated Jessica Simpson, Jennifer Love Hewitt and Jennifer Aniston, was 32 when he got together with 21-year-old Tay. The age difference inspired Dear John, where she accuses a lover of messing with “a girl too young to be messed with”. She said it as “like the last email you’d ever send to someone that you used to be in a relationship with.
Usually people write it then don’t send it. I guess I’m pushing send.” Mayer said he was “humiliated” by the song; Taylor denied he inspired it, calling him “presumptuous”. This short romance also allegedly inspired Ours, Superman, The Story of Us, Would’ve Could’ve Should’ve and I Knew You Were Trouble.
Jake Gyllenhaal
Oct – Dec 2010
The fandom had high hopes for this relationship after the couple spent Thanksgiving together in Brooklyn, at the home of Gyllenhaal’s actress sister, Maggie. But it wasn’t to be. Nobody knows why Tay and the Brokeback Mountain and Donnie Darko actor split up, but everyone knows the songs he inspired, including much of her 2012 album, Red, which includes the greatest ever break-up anthem, We Are Never Getting Back Together.
Conor Kennedy
Summer 2012
Taylor dated the son of Robert F Kennedy Jr and the late Mary Kennedy in 2012, a romance that saw her channeling Jackie Onassis in a stylish (if slightly overdone) melange of blouses, crew-neck cardigans, oversized sunglasses and ballet pumps.
Despite – or perhaps because of – Taylor’s obsession with the Kennedy clan, the relationship only lasted three months. Maybe its brevity is why no details made it into a song; or maybe Tay feared offending America’s most feted family. Some say Everything Has Changed, a duet with Ed Sheeran, pays homage to the Kennedy scion.
Harry Styles
Nov 12 – Jan 13
Two performers at the top of their game, adored by millions, both uniquely accustomed to dealing with hectic performance schedules and crippling levels of fame. What could possibly go wrong? Answer: who cares, so long as you can eke an album out of it? Styles is widely believed to be the inspiration behind Style (subtle, Taylor isn’t) and Out Of The Woods, both of which appeared on her 1989 album (released in 2014).
One year after its release, Taylor revealed in a video that “the number one feeling I felt in the whole relationship was anxiety”. Which is presumably what Styles felt every time he heard the songs. One Direction’s most famous and successful member is noteworthy for many things, one of them being that he prompted Taylor’s life-long (well, 10 years and counting) predilection for British men.
Calvin Harris
March 15 – June 16
This one didn’t end well, despite a promising start. While together, Taylor and DJ Harris (who has produced Rihanna, Dua Lipa and Kylie Minogue) were the highest-earning couple in music, and both made a point of supporting each other’s careers. But the love-fest ended abruptly: her camp claimed he was jealous of her success, his camp accused her of leaking that she’d written lyrics for his hit with Rihanna.
“I know you’re off on tour and need someone new to try and bury like Katy [Perry] etc, but I’m not that guy,” Harris wrote. “Focus on the positive aspects of your life… you’ve earned a great one.” Some claim he’s invoked in High Fidelity, from Midnights, her most recent album.
Tom Hiddleston
June – Sep 2016
Tay’s relationship with Brit No 3 is distinguished mainly by its PDAs, with no occasion too public (the Met Ball!) or private (the beach!) to preclude a bum-grope or a sloppy kiss. Before you could say “publicity stunt”, a rather cringe portmanteau was coined, with #Hiddleswift trending in 2016. Insiders claimed it damaged Hiddleston’s chances of playing James Bond. At least Tom could console himself with being immortalised in song: he’s said to have inspired several on Swift’s 2017 album, Reputation, including Getaway Car.
Joe Alwyn
Oct 16 – Apr 23
Her most enduring relationship of all was with this English actor who was still living with his parents when they met. This was conducted off camera – they’d roam north London disguised in tasteful hats and scarves. In the 2020 Netflix documentary Miss Americana, she described “falling in love with someone who had a really wonderful, balanced, grounded life”. On her 2017 album, Reputation, she details making fun of his accent, and alludes to her “London boy” on her 2019 album, Lover.
Alwyn said it was “flattering” to be Taylor’s muse – and was presumably flattered to co-write and co-produce ten songs on her 2020 albums, Folklore and Evermore (under the pseudonym William Bowery), as well as Sweet Nothings on Midnights. The relationship ended in April, after a respectable six years, despite rumours of engagement. “They are friendly,” said a source. “She has nothing bad to say about Joe.”
Matt Healy
May – June 2023
Sure, healthy relationships are great, but can you write a killer song about them? Exactly. Kind and supportive as Joe was, perhaps Taylor was hankering after some fresh lyrical inspiration. Enter Matty Healy, drunk and clutching a bottle of champagne. She and the 1975 frontman have known each other since 2014, but always denied any romance. To the surprise, bemusement and vexation of the fandom, the needle moved in May, with a source saying the two were “massively proud and excited” about their new union.
But rebound relationships never work – not least when you’re a squeaky clean pop princess, and the rebound in question is with a man who has made odd remarks about the rapper Ice Spice and admitted (on a podcast) to watching hardcore porn. Within two months, it was over. Expect Taylor to pen a song called Bad Romance about him. Oh wait: Lady Gaga already wrote that.
