Taylor Swift’s Past Breakups: Where She Stands With Her Exes Now Amid ‘Tortured Poets Department’

Joe Jonas

Taylor and Joe dated from July until October 2008, when he infamously dumped her over the phone. “When I find that person that 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,” Taylor told Ellen DeGeneres during a stop by her daytime talk show shortly after their split

She went on to write several songs fans believe were about Joe, including “Mr. Perfectly Fine,” which hinted he was totally cool with dumping her.

Taylor and Joe showed how they were on friendly terms in November 13, 2021, when he and then-wife Sophie Turner attended the Saturday Night Live afterparty after the “Cruel Summer” singer appeared as the show’s musical guest.

During an appearance on Dax Shepard’s “Armchair Expert” podcast in May 2023, Joe said things were OK between the two after all the time that had passed. “I’m cool with Taylor. We’re cool,” Joe said before noting about her fanbase, “I hope to think they like me … No one f–ks with the Swifties, you know?”

Following Joe and Sophie’s split in 2023, Taylor seemed to side with the Game of Thrones actress, who reportedly moved into her New York City loft for a period of time. The now-close pals have been seen out and about together frequently since.

Taylor Lautner

The pair had a brief romance in 2009 after working on the 2010 film Valentine’s Day together. She seemed to look back fondly at her ex after their split in the song “Back to December,” referencing his “sweet smile” and “tan skin.”

The “Shake It Off” singer showed how close they remained when he appeared on stage with Taylor at her Kansas City, Missouri, Eras tour stop in July 2023, where the two hugged. She then surprised the audience by premiering the video for “I Can See You,” which starred the Twilight alum and actress Joey King.

“He was a very positive force in my life when I was making the Speak Now album, and I want to say he did every single stunt that you saw in that music video. He and his wife have become some of my closest friends, and it’s very convenient because we all share the same first name,” Swift said of Lautner and his wife, Taylor Dome.

The Home Team actor shared the love, telling his ex, “I respect you so much. Not just for the singer you are, the songwriter, the performer — but truly for the human you are. You are gracious, humble, kind and I’m honored to know you.”

John Mayer

Taylor’s romance with the “Gravity” singer only lasted from December 2009 until February 2010, but resulted in one of her most bitter breakup songs, “Dear John,” from her album Speak Now, which many fans speculated was about the “New Light” crooner.

“It made me feel terrible, because I didn’t deserve it. I’m pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy thing for her to do,” John told Rolling Stone in 2012.

Following the interview, Taylor told Glamour that John was being “presumptuous,” adding, “I never disclose who my songs are about.” However, she added, “I think that song really hit home with a lot of girls who had been through toxic relationships and had found their way to the other side of it. I’ve never looked out while singing a song during a concert to see so many girls crying.”

Ahead of the July 2023 release of Speak Now (Taylor’s Version) she told fans, “I was hoping to ask you, that as we lead up to this album coming out, I would love for that kindness and that gentleness to extend onto our internet activities.”

She continued, “I’m 33 years old, I don’t care about anything that happened to me when I was 19 except the songs I wrote and the memories we made together. So what I’m trying to tell you is that I am not putting this album out so you should feel the need to defend me on the internet against someone you think I wrote a song about 14 million years ago when I was 19.”

The day before the album dropped, John seemed to brace himself, sharing an Instagram photo of drones spelling out “Please be kind.”

Jake Gyllenhaal

Taylor and Jake had a PDA-filled romance from October through December 2010. The Roadhouse actor was long rumored to be the subject of Taylor’s 2012 breakup ballad “All Too Well” from her Red album.

“I look back on this [Red] as my true breakup album, every other album has flickers of different things. But this was an album that I wrote specifically about pure, absolute, to the core, heartbreak,” Taylor said in 2020 in a teaser video for Rolling Stone and Amazon Music’s upcoming “500 Greatest Albums” podcast.

In an updated 10-minute version of “All Too Well” included on Red (Taylor’s Version), which was released in November 2021, Taylor seemed to indicate Jake broke up with her over their nine-year age difference. She included the new line, “You said if we had been closer in age maybe it would have been fine / And that made me want to die.”

Taylor hinted that Jake was OK with the songs on Red in a November 2013 interview with New York Magazine, without naming the Ambulance actor.

“He was like, ‘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,” she recalled. “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.”

Jake was asked about “All Too Well” in a February 2022 interview with Esquire, but said he didn’t listen to Red.

“It has nothing to do with me. It’s about her relationship with her fans,” he said of the song. “It is her expression. Artists tap into personal experiences for inspiration, and I don’t begrudge anyone that.”

Responding to the social media attention that came with the 10-minute version of the song, Jake said, “I’m not unaware that there’s interest in my life. My life is wonderful. I have a relationship that is truly wonderful, and I have a family I love so much. And this whole period of time has made me realize that.” Jake has been dating French model Jeanne Cadieu since 2018.

Harry Styles

While the pair had a brief romance from November 2012 through early January 2013, it resulted in several songs fans believe Taylor wrote about their romance, including “Style” and “Out of the Woods.”

Neither artist publicly discussed their relationship, but Taylor has proved there’s no bad blood by cheering on Harry at several awards shows, including the 2023 Grammys when he took home the coveted Album of the Year win for Harry’s House. Harry and Taylor were caught on camera during a commercial break having a friendly chat in the audience.

Calvin Harris

Taylor dated the DJ and music producer from February 2015 until June 2016. It was one of her more public romances, as the normally private Pennsylvania native shared photos of their vacations in Instagram posts. The “Me” singer even cheered on Calvin during his April 2016 Coachella set.

Things seemed to go south when it was revealed that Taylor wrote Calvin’s hit featuring Rihanna, “This Is What You Came For.” On the day the song was released in May 2016, the DJ told Ryan Seacrest that he and Taylor “haven’t even spoken about” doing a collaboration, adding, “I can’t see it happening.”

Following their split, Calvin went on a Twitter rant in July 2016, writing, “I wrote the music, produced the song, arranged it and cut the vocals though,” about the song, which was released under the pseudonym Nils Sjoberg. “And initially [Taylor] wanted it kept secret, hence the pseudonym.”

Taylor’s rep clarified that the song was all hers, saying, “Taylor Swift wrote ‘This Is What You Came For’ under the pseudonym Nils Sjoberg.”

Calvin then went on to take a swipe at the “Wildest Dreams” artist’s new romance with actor Tom Hiddleston, tweeting, “I figure if you’re happy in your new relationship you should focus on that instead of trying to tear your ex bf down for something to do.” He then said he refused to be involved in a feud such as the one Taylor had with Katy Perry at the time, writing, “I know you’re off tour and you need someone new to try and bury like Katy ETC but I’m not that guy, sorry. I won’t allow it.”

The Scottish DJ went on to marry Vick Hope in 2023, who revealed she was a secret Swiftie, while implying she couldn’t listen to Taylor’s songs around Calvin.

“Soon as my husband goes away, I listen to Taylor Swift,” Vick said during the “Going Home With Vick, Katie and Jamie” radio show in February 2024. “That’s just when I get … just a little fill. Just a couple of songs, get it out of my system. Then it’s done.”

Tom Hiddleston

Taylor began dating The Night Manager actor on the heels of her split from Calvin, although they split in September 2016 as he was due to stay in Australia for months shooting Thor: Ragnarok.

The pair seemed to remain on good terms following their breakup and Tom had nothing but kind words for his ex in a February 2017 interview with GQ.

“Taylor is an amazing woman. She’s generous and kind and lovely, and we had the best time,” he told the publication. Tom explained how they “decided to go out for dinner, we decided to travel… she’s incredible,” but added, “A relationship in the limelight … A relationship always takes work. And it’s not just the limelight. It’s everything else.”

Joe Alwyn

Taylor and The Favourite actor dated for six years, starting in 2016 and breaking up in 2023. The pair were notoriously private about their relationship and were rarely photographed together.

The two cowrote several songs for her Folklore album, where he used the pen name William Bowery. Taylor even gave her then-boyfriend a shout-out while accepting the Album of the Year award at the 63rd Annual Grammy Awards. “Joe is the first person that I play every single song that I write, and I had the best time writing songs with you in quarantine,” she said in her acceptance speech.

Taylor hinted that their too-private romance made her feel cooped up when gushing about boyfriend Travis Kelce in a December 2023 interview after being named TIME‘s Person of the Year.

After saying how happy she was in a public relationship with the Kansas City Chiefs star, Taylor said, “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 [Travis and I are] just proud of each other.”

She added, “Life is short. Have adventures. Me locking myself away in a house for a lot of years, I’ll never get that time back. I’m more trusting now than I was six years ago,” which coincided with the amount of time she was with Joe.

Taylor announced at the 2024 Grammys that she would be releasing a brand-new album on April 19, 2024, called The Tortured Poets Department, saying she’s been working on it for the past two years. It’s believed nearly the entire album will be about her failed romance and breakup with Joe. Ahead of the release, Taylor released a playlist of old songs categorized into the five stages of grief: denial, anger, bargaining, depression, and acceptance.

Matty Healy

The 1975 singer admitted in 2016 to having a “flirtation” with Taylor that dated back to 2014, but made it clear he had no desire to be her “boyfriend. ”

“I don’t do anything else, right, so it doesn’t leave a lot of room for me going out or shagging someone. So, the one time I did have a flirtation with a girl it ends up going everywhere,” he explained, referring to Taylor to Q magazine. “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,” Matty continued. “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.”

Matty seemingly denied ever dating the “Karma” singer, adding, “If I had gone out with Taylor Swift I would’ve been, ‘F–king hell! I am NOT being Taylor Swift’s boyfriend.’'”

Following Taylor’s split from Joe Alwyn in 2023, she was photographed holding hands with Matty in New York City in May of that year. The “Chocolate” singer also attended several of her Eras tour concerts before their month-long fling was over.

“They had fun together, but it was never serious,” a source told Us Weekly at the time. ​The “Betty” songstress began dating boyfriend Travis Kelce by August 2023. Taylor hasn’t appeared to have kept in touch with Matty since parting ways, and he has been dating model Gabriette Bechtel since September 2023.