The newly engaged Taylor Swift, by her own admission, “has a long list of ex-lovers.” (Or “Starbucks lovers,” if you, too, fell victim to a common musical eggcorn.) That lyric from “Blank Space,” penned in Swift’s early 20s when she only had to stand within 10 feet of a vaguely famous man for tabloids to predict wedding bells, is both an eye-rolling rebuke to the press and public and a tongue-in-cheek call-out to her male muses.
That’s the thing about the men Taylor Swift has loved (or at least written a song about): They’re more than a salacious sideshow used to distract from the towering talent of a young female artist. They are the art.
Swift, always the mastermind shaping her own narrative, has made them so. From the high school boy who was the reason for “Teardrops On My Guitar” to the head-over-heels relationship that inspired “Lover” to the early-thirties mind games excoriated in the “Smallest Man Who Ever Lived,” her relationships are the musical equivalent of Michelangelo’s marble.
To quote “The Manuscript,” a recent bonus track: “The Professor said to write what you know / Lookin’ backwards / Might be the only way to move forward.”
As Swift has processed her romantic highs and lows, so have her millions of listeners. Her music has soundtracked our own crushes, situationships, entanglements with narcissists, painful deaths of relationships that were wrong because they just weren’t right.
Sometimes she does it in real time, as with two songs on her latest album believed to be about her fiancé, Travis Kelce, “The Alchemy” and “So High School.”
Swift and Kelce revealed their engagement on Tuesday in a post on Instagram, with several photos showing the couple embrace in their garden fairytale-like proposal. The announcement comes two years after the pair first started dating.
Of course, not every Taylor Swift song is about romantic love — a significant chunk of her work is about misogyny, family, self-doubt, existential panic, friendship — and you don’t need to know the real-life back stories to her songs to relate to them. But tracing the lyrical clues she leaves can add depth (and let’s be real, some sleuthy fun) to the experience, something the queen of Easter egging almost certainly intended.
While the internet pile-ons that can result from falling foul of Swift’s pen (quill, fountain or glitter gel) are not cool, there are worse legacies to leave than being a footnote in one of the biggest artists of all time’s tracklist.
Here’s the roll call of Swift’s known exes, and how they’ve fared personally and professionally since the “Lavender Haze” dissipated, the “Invisible String” was severed and she got “Closure.”
Drew Dunlap (circa 2005)
The relationship: They dated in high school and Drew took Taylor to prom, but broke up when he went away to university. Drew inspired her first single, “Tim McGraw,” the backward-looking ode to a love that ended too soon.
How he’s fared since: He seems to be living an otherwise normal existence as a project manager in Nashville. Note: Among Swifties, there is some discussion around whether he or someone named Andrew Borello was her first boyfriend and the inspiration for “Tim McGraw” and other songs on her debut album. We’ll have to wait for the memoir to find out.
Andrew Hardwick (circa 2006)
The relationship: The unrequited high school crush name-checked in “Teardrops,” Hardwick finally noticed Taylor and showed up on her driveway two years after the song went stratospheric. She apparently said, “Wow, you’re late!”
How he’s fared since: Bar a potential mention in “You’re On Your Own Kid” from Midnights (“I waited patiently / he’s gonna notice me”), Hardwick’s only brush with public attention since has been for a much darker reason: In 2015, he was arrested for child abuse.
Sam Armstrong (circa 2006)
The relationship: Armstrong has the dubious distinction of being the first man that Taylor Swift called out for bad behaviour in song. If the lyrics to “Should’ve Said No” are to be taken literally, he cheated on her while they were in high school, just before she released her first album.
How he’s fared since: It’s unclear; there’s no publicly available info on what he’s done since earning Taylor’s ire.
Stephen Barker Lyles (circa 2008)
The relationship: In the lyrics to the song “Hey Stephen” on “Fearless,” Swift used capital letters to spell out “LOVE AND THEFT,” the name of the country duo Lyles was in, which toured with her for her debut album. The two never dated. In Swift’s own words, “it’s about a guy who I had a crush on and never told him. So I wrote everything that I was thinking down in the song instead of telling him.”
How he’s fared since: Lyles has confirmed that he’s aware of the lyrical tribute — Swift is said to have called and told him about it — and while they don’t seem close anymore, he speaks fondly of her in interviews.
Joe Jonas (2008)
The relationship: After three months of dating, Jonas infamously broke up with Swift in a 27-second phone call. It’s a wound that festered; she brought it up when she appeared on the Ellen DeGeneres show and in her SNL monologue that year. (In a statement on, wait for it, MySpace, Jonas insinuated that she hung up on him, not the other way around.)
How he’s fared since: Jonas is thought to have inspired several songs, notably “Forever & Always,” “Last Kiss” and the vault track “Mr Perfectly Fine.” Career-wise, Jonas is, well, perfectly fine: His solo project, DNCE, spawned the 2015 earworm “Cake By The Ocean,” while the Jonas Brothers have enjoyed a successful reunion tour. He and Swift seemed to become friendly over time, but in 2023 Swift gave well-publicized refuge to Jonas’ ex-wife Sophie Turner when the pair announced their split.
Taylor Lautner (2009)
The relationship: Co-stars in the so-bad-it’s-bad flick “Valentine’s Day,” the two Taylors broke up when he liked her more than she liked him. See: “Back To December” from “Speak Now.”
How he’s fared since: Other than marrying another Taylor? Lautner’s been largely out of the spotlight since his “Twilight” glory days, but Swift has given him some work. He starred in the music video for the “Speak Now” vault track “I Can See You” in 2023, and did a backflip on stage when Swift brought him out at an Eras Tour show.
John Mayer (2009 to 2010)
The relationship: Based on lyrical output, the months 19-year-old Swift spent dating 32-year-old Mayer after they met recording “Half of My Heart” made a lasting, seemingly rather traumatic impression on her. The most poignant references are 2010s “Dear John” and 2022’s “Could’ve, Would’ve, Should’ve.”
How he’s fared since: Mayer has said that “Dear John” was “cheap songwriting” and “a lousy thing to do” that he didn’t deserve. Still, in the run-up to the re-release of the song on Taylor’s Version of “Speak Now,” Swift essentially pre-emptively asked fans not to go after Mayer. “I’m not putting this album out so you should feel the need to defend me on the internet against someone you think I might have written a song about 14 million years ago,” she said.
Jake Gyllenhaal (2010 to 2011)
The relationship: In this next entanglement with an older man, Swift and Gyllenhaal were on-and-off for several excruciating months (“We Are Never, Ever Getting Back Together”) before he ended it over text, goes the lore. It birthed one of Taylor’s most beloved track 5s: “All Too Well,” and the even sharper 10-minute Taylor’s Version.
How he’s fared since: Gyllenhaal has said he doesn’t “begrudge” Swift using their time together as creative fuel. But he’s still best known to many as the guy with the “F — k the patriarchy” key-chain who ruined Taylor’s 21st birthday.
Conor Kennedy (2012)
The relationship: Swift had a summer romance with this scion of an American dynasty during her “I bought a mansion in Rhode Island” era. She’s thought to have penned “Starlight” after hearing his grandparents’ love story.
How he’s fared since: Fine! Uber-private (you would be too if your dad was RFK Jr.), Kennedy recently got engaged.
Harry Styles (2012 to 2013)
The relationship: Swift’s Internet-breaking dalliance with Styles was seemingly confirmed when she was spotted wearing his airplane necklace. It lasted just four months, but inspired several songs on her pop breakthrough album, 1989 (“Out of the Woods,” “Style,” “Is It Over Now?” and “Now That We Don’t Talk” from the vault). In return, she got the One Direction banger, “Perfect.”
How he’s fared since: You know, just having massive success as a solo artist and winning album of the year. He and Swift seem to be friendly, if not close, and were spotted chatting at the Grammys a few years ago.
Calvin Harris (2015 to 2016)
The relationship: After being introduced by Ellie Goulding, Swift dated the Scottish DJ for 15 months. They attended awards shows together, went Instagram official and jetsetted the world. The relationship ended badly and may have involved a little overlap with Tom Hiddleston on Taylor’s part.
How he’s fared since: Under a pseudonym, Swift had contributed lyrics and “oooos” to the Harris-produced Rihanna smash “This Is What You Came For.” Post-breakup, Swift unmasked herself as co-writer of the song, and Harris went on a Twitter rant: “Hurtful to me at this point that her and her team would go so far out of their way to try and make ME look bad.” (He has since said he regrets it.) Famously, Harris was the only boyfriend Swift didn’t write a song about, until the not particularly complimentary “High Infidelity” on “Midnights.”
Tom Hiddleston (2016)
The relationship: This whirlwind three-month romance, supposedly sparked when they met on the dance floor at the Met Gala in May, culminated in Hiddleston wearing an “I Heart TS” shirt at Swift’s Fourth of July party.
How he’s fared since: Hiddleston is now married with a baby and has a fine career as a Marvel villain. He’s thought to have inspired “Getaway Car,” which contains the brilliantly dismissive line, “You weren’t thinking, and I was just drinking.”
Joe Alwyn (2016 to 2023)
The relationship: By any metric the biggest love of Swift’s life so far, she and this spotlight-averse British actor were together for six years, living together and even writing music together. (He’s credited as a co-writer on her pandemic albums “Folklore” and “Evermore” as “William Bowery.”)
How he’s fared since: She’s never commented publicly on the split. While fans hoped Swift would spill the tea on Alwyn in “The Tortured Poets Department,” instead it discreetly paints a picture of a complicated relationship that died a slow, sad death when she didn’t get the commitment she was looking for from him. See: “You’re Losing Me,” “So Long, London” and “How Did It End?” Alwyn, an unknown actor when they met, has kept quietly building an impressive resume, including the Sally Rooney adaptation “Conversations With Friends” and this year’s “Kinds of Kindness,” starring opposite Swift’s friend Emma Stone.
Matty Healy (2023)
The relationship: In one of the more controversial choices of her romantic life, Taylor briefly dated this British musician/provocateur in the spring of 2023. But her infatuation with him extends back to her early twenties, when he seems to have been “The One” that got away during her years in New York.
How he’s fared since: He is thought to be “The Smallest Man Who Ever Lived” from “The Tortured Poets Department,” a collection of songs she’s characterized as a record of “a fleeting and fatalistic moment in time — one that was both sensational and sorrowful in equal measure.” She’s firmly moved on — hi, Travis! — and so has Healy, who’s now engaged to model and internet star Gabbriette. He did, however, recently seem to shade Swift by telling the Doomscroll podcast that “making a record about something that personally happened to me that by the time I put it out is gonna be like two years old … I see people doing that, and it’s just not interesting.”
Correction – Oct. 28, 2024
This article was edited from a previous version that misstated the title of the song, “The Smallest Man Who Ever Lived.”
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