Taylor Swift Ex-boyfriend: For years, Taylor Swift has been serenading us with breakup anthems that feel eerily similar to the ups and downs of our own lives.
The country crooner turned pop sensation has navigated the tumultuous waters of love, leaving a trail of Hollywood heartthrobs in her wake.
From musicians to movie stars, Taylor has gracefully danced through the world of celebrity relationships, weaving her romantic escapades into the fabric of her chart-topping songs.
The list of her ex-boyfriends reads like a who’s who of the entertainment industry, ranging from Jake Gyllenhaal to John Mayer.
Join us on a journey through the timeline of Taylor’s love life, where each romance is immortalized in the lyrics of her unforgettable songs.
And yes, there’s even a recent connection to the NFL with Kansas City Chiefs player Travis Kelce. Let’s dive into the fascinating world of Taylor Swift’s ex-boyfriends and the musical tales that ensued.
Taylor Swift’s Ex-Boyfriends – Every Single Person She Has Dated in The Past!
Curious about the romantic rollercoaster that is Taylor Swift’s love life? Well, get ready to take a trip down memory lane as we spill the tea on every single person the iconic singer-songwriter has dated in the past!
From heartthrobs to musicians, Taylor’s dating history is as diverse as her chart-topping hits. Buckle up for a journey through the ups and downs of her relationships, and let’s explore the fascinating world of Taylor Swift’s ex-boyfriends.
Joe Jonas: July 2008—October 2008
So, let’s talk about Joe Jonas and Taylor – a short-lived romance that somehow became the most dramatic chapter in Taylor Swift’s dating history. The breakup? Oh, it happened over the phone, which Taylor openly spilled during an appearance on Ellen back in November 2008.
She even had this to say:
“When I find that person who is right for me, he’ll be wonderful, and when I look at that person, I’m not even gonna be able to remember the boy who broke up with me over the phone in 25 seconds when I was 18.”
Feeling inspired, Taylor dropped a song called “Forever and Always,” where she sings, “Was I out of line? / Did I say something way too honest, made you run and hide / Like a scared little boy.” Ouch!
“You might think I’d bring up Joe, that guy who broke up with me on the phone. But I’m not going to mention him in my monologue. Hey, Joe! I’m doing real well and I’m hosting SNL—but I’m not going to write about that in my monologue.”
Ah, young love and its public moments!
Lucas Till: March 2009—April 2009
Alright, so Lucas was the guy in Taylor’s “You Belong With Me” video, and apparently, they gave dating a shot for a bit. According to Lucas, he spilled the beans to MTV, saying:
“We dated for a little bit. But there was no friction because we were too nice. We just really both liked each other…[but] most relationships work out ’cause you get along and then you don’t, and then you make up and it’s passionate, and with us, I really just liked her as a friend. That’s the only reason that didn’t work out.”
Well, now we’re in the loop!
Taylor Lautner: Fall 2009
Once upon a Hollywood set, Taylor Swift and Taylor Lautner, famously dubbed “Taylor Squared,” stole our hearts while filming Valentine’s Day.
Their on-screen chemistry was so palpable that it sparked rumors and even led Taylor Swift to pen the soulful “Back to December” in the Speak Now album, supposedly about him.
When asked about the song in 2016, Twilight heartthrob Taylor Lautner simply shrugged it off with a nonchalant “That’s what she does.”
But hold on to your hats because it’s 2023, and the plot thickens! Taylor Lautner, or “TayTay” as some affectionately call him, has since tied the knot with another Taylor (I know, it’s a tongue-twister! 😅).
In a surprising turn of events, the Twilight star made a cameo in the Grammy winner’s music video for “I Can See You.” It’s a twist in the tale that we never saw coming, but hey, it somehow healed something deep within us. Go figure!
John Mayer: December 2009—February 2010
Who could ever forget this infamous chapter in Taylor’s love story? I mean, seriously, it’s etched in pop culture history.
Taylor Swift and John Mayer were a thing for a hot minute, and let me tell you, their breakup was a colossal mess, all thanks to John’s less-than-graceful response to Taylor penning “Dear John” about their fling.
Picture this: John spills the tea in a 2012 Rolling Stone interview, going on about how he never got an email or a call, feeling totally blindsided.
It was like a low blow, especially when he was already down and out. In his own words, “I mean, how would you feel if at the lowest you’ve ever been, someone kicked you even lower?”
And wait for it, there’s more. He goes on to call Taylor’s songwriting kinda cheap, accusing her of abusing her talent just to settle a score. Classic “Wait till he gets a load of this!” move, according to him. Bullshit, right? Ah, the drama of celebrity relationships.
Jake Gyllenhaal: October 2010—January 2011
Back in December 2010, Us Weekly dropped the bombshell that these two lovebirds were an item, treating us to some delightful photos that had the whole universe buzzing.
But hold on, because by January, the same magazine was reporting a complete plot twist – Jake apparently pulled the plug on the relationship out of nowhere.
According to a source back then, it was a sudden 180-degree turn that left Taylor blindsided. The breakup left her feeling upset and hurt, questioning what went wrong.
To add a musical twist to the tale, rumor has it that several tracks on the “Red” album were inspired by Jake, and surprisingly, he was totally cool with it.
Taylor didn’t spill the beans on names, but she did share with New York Magazine that the mystery man told her he listened to the album, describing it as a bittersweet experience akin to flipping through a photo album.
Now, that’s a lot more mature than the crazy emails she received from another guy. It seems love can be both wonderful and terrible, especially when one of the people involved is a songwriter. As Taylor puts it, did he not bother to Wikipedia her before giving her a call?
Connor Kennedy: July 2012—October 2012
Guess what? Us Weekly spilled the beans on Connor and Taylor’s romance when they were caught in the act in Hyannisport, Massachusetts. An eagle-eyed onlooker spilled the deets, saying, “Connor put his arm around Taylor, and they locked lips behind the boat shed.”
But, hold on to your emotions, because the breakup news isn’t all doom and gloom. According to E!, the split was a friendly one, blame it on the pesky distance between them. Still, it’s hard not to feel a bit bummed—imagine Taylor as a casual Kennedy!
Harry Styles: November 2012—January 2013
So, let’s talk about the Harry Styles chapter in Taylor Swift’s dating saga—it’s like a whirlwind romance crammed into just three months, and honestly, it’s a bit exhausting.
The gossip mill kicked into high gear when Taylor was caught rocking Harry’s silver airplane necklace, the same one she flaunted in her “Out of the Woods” video. Coincidence? Maybe not.
Come December, they decided to make it official(ish), flaunting their Central Park Zoo escapades in front of the cameras. But, surprise, surprise, after a mere few months and one solo boat ride that had Taylor looking pretty lonely, Haylor went kaput.
Awkwardness alert! Especially when Taylor threw some shade at Harry during her 2013 Grammys performance, complete with an English accent.
Oh, and let’s not forget “Two Ghosts,” a track from Harry’s debut solo album, rumored to be about our girl Tay. Since the split, they’ve managed to keep things amicable. Fast forward to the 2021 Grammys, where their reunion set the internet on fire, and then again in 2023.
Throw🔙| 11 years ago today, @TaylorSwift13 was spotted with a blue dress on a boat. pic.twitter.com/xlA5uoUEAK
— The Swift Society (@TheSwiftSociety) January 4, 2024
Oh, and about that boat incident? It seems October 2023 gifted us with the release of “1989 (Taylor’s Version),” bringing a flood of Harry-coded lyrics. Case in point: the vault track “Is It Over Now?” Yeah, the drama never really ends, does it?
Calvin Harris: February 2015—May 2016
So, Taylor and Calvin’s love story kicked off at the Elle Style Awards in February. And guess what? We’ve got the photo evidence to prove it!
Fast forward a month, and they’re strolling through Whole Foods in Nashville, looking all cute in matching outfits. Talk about setting the stage for a love story, right?
@taylorswift13 & @CalvinHarris together in matching outfits…that pretty much means they’re going out, yeah!? pic.twitter.com/8KXecnq3An
— Tom and Claire (@tomandclaire) March 27, 2015
Things got real when they went public at the 2015 Billboard Music Awards in May, sealing the deal with a camera-friendly kiss. Fast forward to March 6, 2017 – cue the confetti because it’s their one-year anniversary! But hold on, the plot thickens.
Just two months later, People spilled the tea that Calvin decided to call it quits. The breakup? Oh, it was messy. Calvin even dropped some song lyrics lowkey accusing Taylor of some not-so-great stuff. Ah, the drama of Hollywood love!
Tom Hiddleston: May 2016—September 2016
Remember the time Taylor Swift and Tom Hiddleston had everyone scratching their heads with their unexpected romance? It all kicked off at the Met Gala, where the duo was caught dancing the night away.
Then, bam! June hit, and the Sun dropped photos of them locking lips on a rocky outcrop in Rhode Island. Of course, the internet went wild with questions—like, were those pictures staged or not? From there, it was a whirlwind.
The Loki actor charmed his way into meeting Taylor’s parents in Nashville, they grooved together at a Selena Gomez concert, and there was that unforgettable moment of Tom sporting an “I HEART TS” tank top while frolicking in the ocean with Taylor and a squad of supermodels.
But, alas, the fairytale took a turn in September 2016. Rumors started swirling that Taylor had concerns about Tom’s motives in the relationship. Ah, the twists and turns of celebrity love!
Joe Alwyn: May 2017—April 2023
So, the story of Taylor and Joe kicks off in a rather fancy way – they supposedly met at the Met Gala on the First Monday in May.
Now, no one has officially spilled the beans on this, but eagle-eyed fans seem to think Taylor’s song “Dress” drops some hints, especially with lyrics like “Flashback to when you met me / Your buzz cut / And my hair bleached.” Picture it: Taylor rocking the bleached hair and Joe with the buzz cut on that memorable night.
Fast forward a whole year, and the British tabloid, the Sun, spilled the tea that Taylor and Joe were an item. Rumor had it she’d been in London incognito, and their relationship was apparently “the real deal.” Then, December 2017 rolls around, and Jaylor makes a public appearance, swaying together at an Ed Sheeran concert.
March 2018 brought a sweet touch – Taylor wearing Joe’s initials around her neck. Things progressed, and in September of the same year, sneaky paparazzi caught Taylor sneaking into the premiere of Joe’s movie, “The Favourite.”
Vertical video for #Delicate out now. Only on @Spotify ✨ https://t.co/ZHvrH7k1PN pic.twitter.com/nhcfIv97gR
— Taylor Swift (@taylorswift13) March 30, 2018
Jump to February 2019, and they’re getting cozy at the BAFTAs. The love train kept chugging along, with Joe (aka William Bowery) even joining forces with Taylor on her Folklore album. The two were going strong, Taylor even addressing their six-year romance on her October 2022 album, “Midnights.”
But, alas, all good things come to an end. In April 2023, Entertainment Tonight reported that Taylor and Joe called it quits. No drama, apparently – just a case of the relationship running its course. And that might be why Joe’s been MIA at Taylor’s Eras Tour. Love stories, they’re something else, aren’t they?
Matty Healy: May 2023—June 2023
Let’s rewind the clock to 2014, the year when Taylor Swift and Matty first crossed paths. Starting off as friends, the rumor mill quickly stirred up speculation about a romantic connection between Taylor and The 1975’s frontman. Fast forward to 2016, and things took a bit of a sour turn when Matty made some less-than-friendly comments about the possibility of them dating.
Jump to January 2023: Taylor makes a surprise appearance at The 1975’s show at the O2 Arena in London, belting out “Anti-Hero” live for the first time and even treating the audience to a cover of the band’s song, “The City.”
Then, in May 2023, fresh off her six-year relationship with Joe Alwyn, dating rumors with Matty resurface. According to Entertainment Tonight, an anonymous source spilled the beans, revealing that “Taylor and Matty have been hanging out recently, and Jack Antonoff reconnected them.”
However, after some questionable remarks from Matty about Taylor’s friend and “Karma” collaborator, Ice Spice, it seems their connection hit a speed bump, and they decided to part ways.
Travis Kelce: July 2023—Right Now
Alright, so picture this: July 2023, Taylor Swift’s Eras Tour hits Arrowhead Stadium in Kansas City, and guess who’s in the audience? None other than Travis Kelce, the Kansas City Chiefs’ tight end. Travis Kelce crafts a friendship bracelet with his digits on it, hoping to catch Taylor’s attention.
Fast forward to a December 2023 interview, where Taylor spills the beans, admitting they’d been low-key dating since the bracelet incident. No grand first-date spectacle, just a genuine connection blossoming under the radar.
Taylor’s seen cheering at Chiefs games, Travis returns the favor at her Argentina tour stop, and they share a cute New Year’s kiss in 2024. And that, my friends, brings us up to the present in the adorable world of Tayvis. Thanks for tuning in to my Tay talk!