Taylor Swift, the Romantic: The Ex-boyfriends of TayTay

Just like any of us, Taylor Swift also had a problematic love life before finally finding her stability in relationships. So, here is a rundown of her past romances.

Taylor Swift seriously gets way too much hate for dating celebs and then turning her love life into songs. But let’s be real - if Tay was not so open and real about her exes and feelings, we would not have half of her iconic discography. ‘The Tortured Poets Department’? Absolute gold. Her re-records? Chef’s kiss. (Vault tracks = pure emotional chaos, and yes, we are still recovering from the John Mayer jabs.) And let’s not forget the masterpiece that is ‘All Too Well (10 Minute Version)’ - a heartbreak anthem born from her “twin flame bruise” era. Legendary.

So, instead of roasting her, maybe thank her for the bops? Anyway, let’s rewind and look at the lucky folks who got a front-row seat to Taylor’s love life. (Hi again, Tom Hiddleston—remember the “I ♥ T.S.” shirt? Iconic behavior.)

Jone Jonas (July 2008 - October 2008)

Joe and Taylor did not date for long, but their breakup was super messy. It got extra dramatic because Joe dumped her over the phone - something Taylor straight-up confirmed during an interview on Ellen back in November 2008: “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.”

Later on, Taylor dropped a song called “Forever and Always” that was clearly about Joe. One part of the lyrics says, “Was I out of line? / Did I say something way too honest, made you run and hide / Like a scared little boy.”

Yeah... that line definitely stings!

Even though Taylor later said sorry for calling the Jonas brother out, fun fact: back in 2009, she still brought up their breakup during her opening monologue on Saturday Night Live. She said, “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.” (source)

Lucas Till (March 2009 - April 2009)

So, Lucas was the dude in Taylor’s ‘You Belong With Me’ music video, and it looks like they dated for a little bit. At least, that is what Lucas said in an interview with MTV. He said, “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.” (source)

Taylor Lautner (Fall 2009)

Looks like Taylor Lautner really does have a thing for Taylors. Before he married Taylor Dome, he dated Taylor Swift for a short time. Just like in the movie Valentine’s Day, the romance carried over off-screen, too.

The two were spotted getting close during their three-month fling in 2009, going on cute dates like sitting rink-side at a hockey game. That same year, Swift gave him a playful shoutout during her Saturday Night Live monologue, saying, “If you’re wondering if I might be dating the werewolf from Twilight… I’m not gonna comment,” then smiled, mouthed “Hi, Taylor,” and blew a kiss to the camera. (source)

Taylor supposedly wrote the song ‘Back to December’ from her Speak Now album about him. When someone asked Twilight Taylor in 2016 what he thought about it, he just shrugged it off and said, “That’s what she does.” However, their romance fizzled out soon, and now they ae just good friends!

John Mayer (December 2009 - February 2010)

Who could ever forget this relationship? Literally no one. Taylor and John Mayer dated for only a few months, but the breakup was super messy, mostly because John did not take it well when Taylor dropped ‘Dear John’, which was clearly about him.

You might be thinking that we are exaggerating John’s reaction to the song, but you are wrong. In a 2012 interview with Rolling Stone, Mayer said, “I never got an email. I never got a phone call. I was really caught off guard, and it really humiliated me at a time when I’d already been dressed down. I mean, how would you feel if at the lowest you've ever been, someone kicked you even lower?” The singer further added, “I will say as a songwriter that I think it’s kind of cheap songwriting. I know she’s the biggest thing in the world, and I’m not trying to sink anybody’s ship, but I think it’s abusing your talent to rub your hands together and go, ‘Wait till he gets a load of this!’ That’s bullshit.” (Source)

Jake Gyllenhaal (October 2010 - January 2011)

Us Weekly revealed that Taylor Swift and Jake Gyllenhaal were dating in a cover story back in December 2010. By January, the magazine shared that Jake suddenly broke up with Taylor out of nowhere. A source said, “It was a total 180 and came out of the blue. Jake just told her it wasn’t working.” According to the source, Taylor was super upset and hurt. She did not understand what went wrong and felt like he totally blindsided her.

A bunch of songs on Red were allegedly inspired by Jake, and he was completely cool with them. Taylor did not exactly name names, but she did tell New York Magazine that the man in question told her, “‘I just listened to the album, and that was a really bittersweet experience for me. It was like going through a photo album.’ That was nice. Nicer than, like, the ranting, crazy emails I got from this one dude. It’s a lot more mature way of looking at a love that was wonderful until it was terrible, and both people got hurt from it—but one of those people happened to be a songwriter. So what are you going to do? Did you not Wikipedia me before you called me up?” (Source)

Harry Styles (November 2012 - January 2013)

Back in December, Taylor and Harry made their relationship public when they were spotted walking around Central Park Zoo together. What seemed to confirm their romantic relationship was when both were spotted sharing a kiss at midnight at Times Square, New York, on New Year's Eve.

But after only a few months - and one trip where Taylor was seen sitting alone on a boat - Haylor called it quits. Things got kinda awkward, especially when Taylor shaded Harry at the 2013 Grammys by using a British accent during her performance.

Harry’s song ‘Two Ghosts’ is rumored to be about her. But despite everything, they have stayed on good terms. They were even seen chatting at both the 2021 and 2023 Grammys, which totally blew up the internet.

Oh, and when ‘1989 (Taylor’s Version)’ dropped in October 2023, fans got plenty of Harry-coded lyrics - like the ones in the vault track “Is It Over Now?”

Calvin Harris (February 2015 - May 2016)

Taylor and Calvin first met at the Elle Style Awards in February. Just a month later, they were seen wearing matching outfits at a Whole Foods in Nashville - pretty much giving us the perfect rom-com moment. They made their relationship official at the 2015 Billboard Music Awards in May, even sharing a kiss on camera. The two celebrated their first anniversary on March 6, 2017. But just two months after that, People reported that Calvin ended the relationship. Things got messy fast, with Calvin hinting in his song lyrics that Taylor might have cheated.

Tom Hiddleston (May 2016 - September 2016)

Remember when Taylor dated Tom Hiddleston? If not, here is a little throwback. Their unexpected romance kicked off at the Met Gala, where they were spotted dancing together and having a blast.

In June, photos of Taylor and Tom kissing on some rocks in Rhode Island were published by The Sun. And of course, the internet went wild with questions - like, were those pics staged or not? After those photos blew up online, things between Taylor and Tom moved fast. He met her parents in Nashville, they were seen dancing at a Selena Gomez concert. Tom even wore a tank top that said “I HEART TS” while hanging out in the ocean with Taylor and a group of supermodels.

Sadly, things ended for Taylor and Tom in September 2016. Sources said Taylor started to feel like Tom might not have been with her for the right reasons.

Joe Alwyn (May 2017 - April 2023)

Taylor and Joe probably met at the Met Gala (aka the first Monday in May). It has never been officially confirmed, but fans believe her song ‘Dress’ hints at it with lyrics like: “Flashback to when you met me / Your buzz cut / And my hair bleached.” Sounds like a Met Gala moment!

A year later, the British tabloid The Sun revealed that Taylor and Joe were dating. They said Taylor had been secretly living in London and that the two were “the real deal.” In December 2017, fans saw them slow dancing at an Ed Sheeran concert. Then, in March 2018, Taylor was spotted wearing a necklace with Joe’s initials on it.

In February 2019, Taylor and Joe were seen looking really close at the BAFTAs. Their relationship stayed strong for a long time, with Joe (using the name William Bowery) even helping Taylor write songs on Folklore. Taylor also talked about their six-year relationship on her ‘Midnights’ album, which came out in October 2022.

In April 2023, Entertainment Tonight shared that Taylor and Joe had broken up. According to sources, the breakup was not messy or dramatic - their relationship had just naturally come to an end. That is also why Joe had not been seen at any of Taylor’s shows during her Eras Tour.

Matty Healy (May 2023 - June 2023)

Right, let’s go back to 2014. That is when Taylor and Matty first met. They were just friends at first, but soon, people started guessing they might be more than that. In 2016, Matty made some not-so-nice comments about the idea of them dating, which added even more fuel to the rumors.

In an interview with Q magazine, Healy said, “So the one time I did have a flirtation with a girl, it ends up going everywhere...I mean, I got on E! News and people were like, 'Who's Matt Healy?' so that was cool. But I didn't make a big deal out of it myself. It's not really anything to talk about, because if she wasn't Taylor Swift we wouldn't be talking about her. She wasn't a big impact on my life.” “It's just interesting to me how interested the world is about Taylor Swift. The reason I mention that is because if I had [properly] gone out with Taylor Swift, I would've been, 'F***ing hell, I am not being Taylor Swift's boyfriend. You know, "F**k. That."' That's also a man thing, a de-masculinating, emasculating thing,” he continued. (source)

Jump to January 2023: Taylor surprised everyone by showing up at The 1975’s concert at the O2 Arena in London. She performed ‘Anti-Hero’ live for the first time and even covered their song ‘The City’. By May 2023, dating rumors started flying again, especially since Taylor had just split from Joe Alwyn. Sources told Entertainment Tonight that she and Matty were hanging out again, thanks to Jack Antonoff reconnecting them. But things cooled off quickly after Matty made some shady comments about Ice Spice, one of Taylor’s friends and her ‘Karma’ collab buddy.

Travis Kelce (July 2023 - Present)

Alright, here we are in Taylor’s current dating era. In July 2023, she took her Eras Tour to Arrowhead Stadium in Kansas City, the home turf for NFL star Travis Kelce, who plays for the Chiefs. Travis went to the concert and had a whole plan: he made a friendship bracelet with his phone number on it to give to Taylor. Bold move, right? “If you’re up on Taylor Swift concerts, there are friendship bracelets, and I received a bunch of them being there, but I wanted to give Taylor Swift one with my number on it,” Kelce said on one of his New Heights podcast episodes.

Even though he didn’t get a chance to make his move at the time, it looks like fate (and that friendship bracelet) had other plans… because not long after, Taylor basically confirmed that they started dating.

“This all started when Travis very adorably put me on blast on his podcast, which I thought was metal as hell,” Taylor told TIME during an interview in December 2023. “We started hanging out right after that. So we actually had a significant amount of time that no one knew, which I’m grateful for, because we got to get to know each other. By the time I went to that first game, we were a couple. I think some people think that they saw our first date at that game? We would never be psychotic enough to hard launch a first date.”

Swift continued, “When you say a relationship is public, that means I’m going to see him do what he loves, we’re showing up for each other, other people are there and we don’t care. The opposite of that is you have to go to an extreme amount of effort to make sure no one knows that you’re seeing someone. And we’re just proud of each other.”

Taylor showed up to not just one but two Chiefs games in September 2023 to cheer Travis on, and things took off from there. Travis later flew out to Argentina to see her Eras Tour, and she even changed the lyrics to ‘Karma’ for him. By the end of the year, their romance kept getting cuter. With sweet moments at the Super Bowl and a Coachella appearance, it was like life in a fairy tale - all before she dropped ‘The Tortured Poets Department’.

And now? They are going stronger than ever!