YOU ARE WINNER
Oh honey, if there’s one thing that gets the Swifties (and, let’s be real, everyone else with Wi-Fi) buzzing, it’s Taylor Swift’s dating history. The pop star’s relationships have been splashed across every magazine, dissected in every music video, and immortalized in more breakup ballads than we can count. So let’s not pretend you’re not curious: which of Taylor Swift’s ex-boyfriends were actual heartthrobs, and which ones deserve a one-way ticket on the Getaway Car express?
Grab your iced coffee, make sure “Cruel Summer” is playing in the background, and let’s rank Taylor Swift’s exes—from the swoon-worthy to the straight-up tragic. This is your ultimate guide to Taylor Swift’s ex-boyfriends, told by a Swiftie who has watched every era, cried to every “Last Kiss,” and survived the Dear John phase. You’re in safe hands.
1. Joe Alwyn — The Secret Muse
Let’s talk about the man who quietly reigned over Taylor Swift’s life for six years: actor Joe Alwyn. Yes, the actor, the mystery, the co-writer behind the pseudonym William Bowery. If you blinked, you might’ve missed their entire relationship because it was that lowkey. But don’t let the lack of paparazzi photos fool you—Joe Alwyn left a major mark.
Joe gave us the Lover era. He inspired tracks like “Invisible String,” “Peace,” “Daylight,” and “Call It What You Want.” He was by Taylor’s side when she was reclaiming her masters, surviving the media frenzy, and navigating a new creative era. This wasn’t a whirlwind tabloid romance—this was deep, poetic, stable love.
He even co-wrote songs like “Exile” and “Betty” on Folklore, adding his own quiet artistry to Taylor’s discography. When Swift announced their breakup, it was like the end of a novel you didn’t want to finish. Joe wasn’t just another name in Taylor Swift’s dating history. He was the man who helped shape her most emotionally rich albums.
2. Taylor Lautner — The Sweetheart Who Got Away
The fact that Taylor wrote the apology song “Back to December” about Taylor Lautner should tell you everything. This man did nothing wrong. He brought her water when she was dehydrated, remembered anniversaries, showed up. He was, as the kids say, the blueprint.
Their relationship started on the set of “Valentine’s Day,” and while it was short-lived, it was real and sweet. No drama. No shade. Just two attractive Taylors (hello Taylor Squared) trying to make it work. And now? Taylor Lautner married Taylor Dome and is still in Swift’s good graces. He even made a cameo in her music video for “I Can See You” during the Eras Tour.
He’s that rare ex who remains a friend, a fan, and a full-on gem. That alone rockets him to the top.
3. Harry Styles — The Iconic Mess
When Taylor dated Harry Styles, it was the stuff of tabloid gold. We’re talking Central Park strolls—including being photographed together at the Central Park Zoo—New Year’s kisses, and snowmobile crashes. It was chaotic, p***ionate, and dramatic enough to inspire some of Taylor’s best work—“Style,” “Out of the Woods,” and possibly “I Know Places”.
But let’s be real—these two were not ready for each other. Harry was still in full teen-idol mode, and Taylor was knee-deep in rising superstardom. They were too young, too famous, and too followed. And it showed. That snowmobile accident? That wasn’t a metaphor. That was their love life.
But the fact that they hugged at the Grammy Awards years later proves that whatever they had, it left a spark. Their brief romance was a perfect storm of chaos and chemistry.
4. Tom Hiddleston — The Whirlwind Rebound
“I < 3 T.S.” tank top. That’s all I need to say.
Tom Hiddleston was the rebound from Calvin, and it showed. It was like Taylor flipped the switch from secretive to overexposed in a matter of weeks. They went from meeting at the Met Gala to kissing in Rhode Island and the Kennedy compound faster than you could say “Getaway Car.”
It was intense, dramatic, and very, very public. Swift’s breakup with Tom Hiddleston in 2016 drew significant media scrutiny, with their high-profile romance and the pressures of fame often cited as reasons for the split. But here’s the thing: Tom liked her. He was proud to be seen with her. He just wasn’t ready for the PR hurricane that comes with dating Taylor Swift.
Still, he gave us the song “Getaway Car,” and that alone makes his place in Taylor’s history iconic.
5. Conor Kennedy — The American Royalty Romance
If Taylor’s dating history were a coming-of-age novel, the chapter with Conor Kennedy would be titled “Hopelessly Romantic With a Side of Rich-Boy Drama.” At just 18, Conor was still basically figuring out how to survive high school gym cl*** when Taylor—then 22—swooped into his New England world wearing vintage dresses and cardigan energy.
The Conor Kennedy Swift relationship drew attention not only for their four-year age difference but also for the influence of the Kennedy family, which added a layer of intrigue and legacy to their romance.
But make no mistake: this wasn’t just a summer fling. Taylor dove headfirst into this relationship like she was auditioning for The Princess Diaries. She bought a house near the Kennedy compound in Rhode Island, allegedly without even telling her team. The Swifties were collectively like, “Girl, slow down,” but Taylor was deep in her Camelot fantasy.
Rumor has it “Starlight” was inspired by a Kennedy family story, and Everything Has Changed carried some of that dreamy, young-summer-love glow. It was whirlwind, dramatic, and had that tragic romanticism of a Lana Del Rey B-side.
Also? Ethel Kennedy reportedly adored her. That’s Kennedy gold. The relationship may not have lasted, but it gave us a glimpse into Taylor’s belief in big, grand, fairytale-style love—and just how hard she’ll chase it when she thinks she’s found it.
6. Matty Healy — The Tortured Poet Disaster
Okay, buckle up. This is the relationship that no one saw coming but absolutely couldn’t stop watching. Matty Healy, lead singer of The 1975, cigarette in one hand, chaos in the other, strolled into Taylor’s post-Alwyn life like a human Molotov blocktail.
Their chemistry? Off-the-charts messy. It was a cruel summer for Taylor—a tumultuous, emotionally charged romance that inspired some of her most intense songs. He appeared at her Eras Tour shows, was spotted leaving her recording studio, and even introduced her to his band’s fans during a live show. They didn’t confirm anything officially, but the PDA and paparazzi moments screamed something was happening. And then? It disappeared. Poof. No closure. No goodbye. Just gone.
But Matty’s legacy lives on—and not just in our shocked group chats. According to Swiftie theories (and let’s be honest, we’re usually right), several tracks on “The Tortured Poets Department” are basically a lyrical autopsy of this short, chaotic romance. We’re talking “The Smallest Man Who Ever Lived,” “But Daddy I Love Him,” “I Can Fix Him (No Really I Can),” and of course, the title track The Tortured Poets Department.
If Joe Alwyn was her calm and stability, Matty was the romantic equivalent of lighting a match in a fireworks factory. He brought her out of her sadness—and right into another mess. And yet, the songs? Absolute bangers.
So, was it healthy? No. Was it iconic? Also no. But was it art? 100%.
7. Adam Young — The Love Letter That Fell Flat
Before there were public breakups, Grammy wins, and viral Eras Tour TikToks, there was a soft, dreamy spark between Taylor and Owl City’s Adam Young — the sweet, nerdy frontman of Owl City. And if you’re scratching your head going, “Wait… who?” you’re not alone. This one’s deep-cut Swiftie lore.
Taylor met Adam briefly — and by briefly, I mean one magical night that she turned into a whole song. That song? “Enchanted.” It’s pure fairy dust and teenage fantasy bottled into five minutes of lyrical sparkle. The way she sings, “This night is sparkling, don’t you let it go,” practically screams, “I met a man who complimented my eyeliner and now I’ve planned our wedding.”
So what happened next? Adam — bless his dorky heart — responded publicly. He covered the song and added his own lyrics to tell Taylor he felt the same. Sweet, right? Except it came off kind of…awkward. Think Valentine’s Day card from your lab partner.
And then? Crickets. The spark didn’t ignite. No follow-up date. No red carpet sightings. Just a polite, overly formal email exchange with background music. Honestly, it felt like a YA novel that got canceled before chapter two.
Still, Adam Young may be the only man on this list who didn’t screw up, didn’t ghost her, didn’t write a petty tweet. He simply failed to match the wattage of her romantic imagination. But you know what? He got “Enchanted.” And that’s not nothing.
READ NOW: Taylor Swift engaged—did we just enter a brand new era?!
8. Lucas Till — The Music Video Crush
Lucas played her love interest in the “You Belong With Me” music video, taking us back to when Taylor was rocking curly hair, sundresses, and living her teen rom-com fantasy.
You’d think their onscreen chemistry would lead to fireworks in real life. And it did… for like, a week. Taylor and Lucas reportedly dated very briefly in 2009, and the vibe was wholesome, squeaky-clean, and honestly? A little boring.
Lucas later revealed in an interview that there just wasn’t any real spark. “We dated for a bit. But there was no friction because we were too nice.” Translation: there was no drama, and Taylor Swift doesn’t do bland.
There’s no confirmed breakup song for Lucas — though fans like to imagine “You Belong With Me” was her visual love letter to the type of guy she wished would fight for her IRL. He’s the definition of a blink-and-you’ll-miss-it romance. Harmless, sweet, and about as memorable as your 7th grade Valentine.
But let’s give credit where it’s due. Lucas Till exists forever in Taylor’s visual canon — a floppy-haired dreamboat frozen in 2009 nostalgia.
9. Jordan Alford — The First Burn
Every queen has to start somewhere, and for Taylor, it all began with Jordan Alford — a high school ex who ended up being the blueprint for her early fierce lyrics. While he’s not a household name, Jordan deserves a permanent seat in the Swiftie archives for inspiring “Picture to Burn.” In fact, Jordan was the inspiration behind a few songs in Taylor’s early career, making his impact on her music especially memorable.
So what did he do? Oh, just dated one of Taylor’s friends after dumping her. Messy, right? Taylor, being the lyrical wizard she is, turned her teen rage into a guitar-smashing country anthem complete with the iconic line, “I hate that st*pid old pickup truck you never let me drive.”
This was pre-fame Taylor, y’all. The Nashville-dwelling, curly-haired teen still figuring out how to channel betrayal into art. And boy, did she figure it out fast. “Picture to Burn” was the early warning shot — a promise that no breakup would ever go undoblockented again.
Jordan didn’t just break up with Taylor Swift. He unknowingly lit the match that would set off a whole career of musical revenge and lyrical clapbacks. He may have disappeared into small-town obscurity, but his place in Taylor’s dating history? Forever burned in.
10. Jake Gyllenhaal — The Birthday Ghoster
Jake Gyllenhaal, the man who allegedly didn’t show up to Taylor’s 21st birthday party and then ghosted her. That alone is unforgivable. But wait, it gets worse—he inspired “All Too Well,” arguably one of the most gut-wrenching songs in Taylor’s catalog.
He dated her when she was 20 and he was in his 30s. That age gap? Problematic. That scarf? Legendary. Their whole saga screams red flags. The lyric about how her “dress cried” captures the emotional impact of their breakup, highlighting the regret and innocence lost. While he was a terrible boyfriend, we have to give credit where it’s due: the man inspired an era. The “Red” album, the re-record, the short film—he’s a villain in the Swift Cinematic Universe. And can we ever forget? The “All Too Well 10 Minutes Version” we once thought, was a myth. That was real iconic.
Jake Gyllenhaal may want to pretend none of this happened, but Swifties will never forget.
11. Joe Jonas — The 27-Second Call That Launched a Thousand Songs
Joe Jonas: the boyband heartthrob who taught a teenage Taylor what heartbreak felt like—in less than 30 seconds. Yep, he infamously broke up with her over the phone in what’s now known as the 27 second phone call. It was the breakup heard ‘round the pop world, and Swift didn’t hold back. Instead of sulking in silence, she grabbed her guitar and turned the pain into pop culture gold.
From “Forever & Always” to “Better Than Revenge”, the heartbreak also inspired the emotional ballad “Last Kiss” as part of Taylor’s response to the breakup. Years later, she even dubbed him “Perfectly Fine Joe Jonas” in her song “Mr. Perfectly Fine”, highlighting her candid storytelling about her exes. Joe’s legacy lives in every scorched lyric and sarcastic eye roll. She even called him out on “The Ellen DeGeneres Show”, which gave us one of the best petty celebrity moments of the 2000s.
To be fair, time has softened the blow. They’re cool now—Taylor’s since admitted she was a little dramatic (her words, not mine), and Joe has grown into a chill dad who probably wishes he’d handled things a little better. But no matter how mature they are now, Joe will forever be “the guy who broke up with Taylor Swift in less time than it takes to heat a Hot Pocket.” Iconic? Kind of. Reversible? Never.
12. Calvin Harris — The DJ With a Beat and an Ego
When Taylor and Calvin got together, we thought we were witnessing the power couple of the decade. She was America’s lyrical sweetheart; he was a globally famous DJ with the hottest tracks on the charts. They had style, looks, and matching Instagram vacation photos. Everything screamed long-term potential… until it didn’t.
Their relationship was thrust further into the spotlight when they appeared together at the Billboard Music Awards, making headlines with their public display and fueling media speculation about their romance.
Behind the scenes? A PR disaster in slow motion. When Taylor revealed she had co-written “This Is What You Came For” under a pseudonym, Calvin had a full-on Twitter meltdown. It was p***ive-aggressive tweets, unfollows, and subtweet warfare. The breakup didn’t just go public—it exploded.
Taylor didn’t write a full Calvin diss track (that we know of—”I Forgot That You Existed” might be a wink), but this relationship marked a shift. After Calvin, she stopped playing nice. The gloves came off. “Reputation” was brewing, and you could feel the thunder rolling in. Some fans believe that Taylor’s hit songs from this era, including “I Forgot That You Existed”, were inspired by her experiences with Calvin Harris. Calvin may have made bangers in the club, but he couldn’t keep up with the beat of Taylor’s emotional evolution.
13. John Mayer — The Walking, Talking, Musical Cautionary Tale
John Mayer. Oh boy. Where do we even begin? He was older, suave, mysterious—and apparently emotionally allergic to accountability. When Taylor dated John, she was 19 and he was in his 30s. The age gap? Questionable. The power imbalance? Gigantic. The emotional fallout? Catastrophic.
Then we had Dear John—a lyrical obliteration so sharp and devastating that even John himself said it humiliated him. But maybe don’t date a teenage songwriter and then be surprised when your ghosting ends up on a platinum album? The lines “Don’t you think I was too young to be messed with?” hit harder than most diss tracks ever could. Some critics even accused Taylor of ‘kind of cheap songwriting’ in her response to Mayer, suggesting the song was too personal or simplistic.
And when she re-recorded “Speak Now”? The Swifties were foaming at the mouth, ready to rumble. Taylor even had to tell them to be nice, which is Swiftie code for “this man’s still on thin ice.”
John Mayer may be talented, but in the Taylor Swift Cinematic Universe, he’ll forever be cast as the cautionary tale your mother warns you about. And that, dear reader, is why he’s last. Because karma really is Taylor’s boyfriend.
From Heartbreaks to Hit Songs
If there’s one universal truth in this wild, glitter-coated universe of Taylor Swift’s dating history, it’s this: no matter how much these men tried to dim her sparkle, she always turned their mess into magic. As a Grammy winner, Taylor Swift’s personal life has fueled her artistic success and shaped her public persona. Every mistake, every red flag, every dramatic 27-second call—they all became lyrics, and those lyrics became anthems.
She’s the mastermind. They’re just chapters.
So to the men who loved her, lost her, and got locked in her lyric vault: congratulations. You may have broken her heart, but she broke the charts. And for the next guy who thinks he can step into her spotlight and play games? You’re already a verse in progress, babe.
Long live the queen of turning breakups into Billboard gold. And if you’re one of her exes reading this? Sleep with one eye open—she might be recording again.
UP NEXT: The Life of a Showgirl: Taylor Swift’s Glamorous New Era
MOTIVATIONAL AND INSPIRATIONAL
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