A Complete History Of Taylor Swift's Boyfriends

Okay. As a master of writing love songs, it's natural to be curious about Taylor's love life.

Taylor—who is currently on a 52-show, sold-out stadium tour—just performed three consecutive nights in Nashville to 70,000 people (each night) and is considered one of the most prolific musicians of her time. She also just announced Speak Now (Taylor's Version), dropping July 7, which will be her fourth album drop in the last three years.

And while these men may provide some subtext to her discography, continue down this list and know that Taylor is much more than her romantic relationships.

A new "London Boy" may have entered Taylor's life recently. Matty Healy, the frontman for The 1975, is rumored to be dating her, according to reports first broken by The Sun.

While this news had many Swifties rolling their eyes, Matty may very well be Taylor's newest "Lover." The Brit was spotted at the Nashville leg of The Eras Tour this weekend (and was even filmed jamming out to songs). He also performed with Phoebe Bridgers during her opening set.

Matty and Taylor have been hinting at a potential romance brewing. At a recent The 1975 show in Manila on May 3, Matty mouthed "This is about you, you know who you are. I love you," before the band played their hit "About You."

Two days later, just before she sang her song "cardigan," Taylor mouthed the exact same line, word for word. She even said something interesting about Speak Now before performing its track, "Mine."

"It's really crazy to go back and listen to these songs that at the time were fantasy but now [are] really relatable to me," Taylor said.

Beyond that, Taylor and Matty were photographed over the weekend in a car together in photos obtained by The Daily Mail. Entertainment Tonight also reported the two are "having a good time hanging out."

Taylor, pictured wearing a The 1975 T-shirt in 2014, was once rumored to be dating Matty. And in 2014, she did an infamous paparazzi walk a few days after attending the band's show in Los Angeles.

Matty later returned the favor and wore a 1989 T-shirt—Taylor's latest album at the time—onstage at a subsequent show. He was later asked if he was in a relationship with Taylor, which he was quick to deny. But he did expressed his interest in the singer: "I mean, bloody hell, what am I going to do, go out with Taylor Swift? She’s a sensation. I wouldn’t say no," Matty told an Australian radio station, per Page Six. "There’s no, like, relationship or anything happening."

More recently, Taylor debuted her song "Anti-Hero" and performed it live for the very first time at a 1975 show in London last fall. During the show, Matty (who is known to kiss fans during his sets) admitted he wouldn't be snogging anyone that night. "I'm not kissing anybody in front of Taylor Swift, have some respect," Matty said. "In front of the Queen? It's not happening."

Some fans speculate that this could all be one of Taylor's masterful Easter eggs promoting an upcoming song drop (perhaps with a Matty Healy feature), but that commitment to the bit seems excessive, even for Taylor.

Entertainment Tonight also reports that Taylor and Matty reconnected via Jack Antonoff, who is a known Swift collaborator. (Antonoff produced The 1975's latest album Being Funny In A Foreign Language.)

Whether or not she is dating Healy, it's pretty evident that Taylor is no longer dating Joe Alwyn.

Last month, Entertainment Tonight broke the news that Taylor's Joe Era was reportedly over and done."It was not dramatic," an insider told the outlet. "The relationship had just run its course. It's why [Alwyn] hasn't been spotted at any shows."

Neither Joe nor Taylor have officially commented on the reports, but PEOPLE confirmed the news, and a video of Taylor getting choked up while singing "Champagne Problems" on tour went viral on TikTok.

Taylor also subtly deleted an Instagram reel that detailed some parts of her relationship with Alwyn just before Midnights dropped. Plus: She switched out "invisible string," a song pretty clearly about Joe, with "the 1," a song about a break up, on The Eras setlist.

Taylor and Joe's breakup was nothing short of surprising. Throughout their six-year relationship, Taylor released several songs that were sublty about Joe, including Lover's "Cornelia Street," which paid homage to the New York City rental that Taylor was living in when she began dating Joe. Fans were quick to memorialize the spot after the split went public, per Vulture, leaving flowers outside (although Swift has not lived there in many years).

The relationship seemed so formidable because Joe was given credit for co-writing several of Taylor's songs under the pseudonym William Bowery, including "Sweet Nothing," "exile," and "betty." He even won a Grammy for Taylor's album folklore.

Joe, who confirmed he used the pseudonym on The Kelly Clarkson Show in 2022, said: "We chose to do it so the people first and foremost would listen to the music first before dissecting the fact that we did it together.”

Joe has not yet publicly spoken about his split from Taylor, but the pair kept their relationship extraordinarily private, so it's unlikely he ever will.

Emphasis on briefly, but this relationship was a cultural moment in summer 2016. Taylor had her short-lived bleached hair, and Tom wore that infamous “I <3 TS” T-shirt, which was later referenced in Taylor's "Look What You Made Me Do" music video.

The pair reportedly first linked up at the Met Gala in 2016, when they were filmed dancing. This relationship may have inspired Taylor's songs "High Infidelity" (as this relationship somewhat overlapped with her relationship with Calvin Harris) and "Getaway Car" (as Taylor started dating Joe Alwyn pretty soon after breaking things off with Tom).

In fact, the "Getaway Car" lyrics spell out just why things ended between them: "With three of us, honey it's a sideshow / And a circus ain't a love story, and now we're both sorry (we're both sorry)"

"Taylor felt he wanted to take the relationship to be too public," a source told E! News at the time of their split, "and she was not happy about it, and thought it was too much publicity."

Taylor and the British DJ reportedly met through mutual friend Ellie Goulding in 2015 at The Brit Awards and hit it off. They dated for about a year before breaking up in 2016.

After their split, it was revealed that Taylor had actually ghost written Harris' hit “This Is What You Came For” and there was a lot of back and forth about why she wasn’t credited properly.

Harris later fired back on Twitter, writing “I wrote the music, produced the song, arranged it and cut the vocals though. And initially [Swift] wanted it kept secret, hence the pseudonym.”

And in a now-deleted tweet Harris took a jab at Taylor with, “I know you’re off tour and you need someone new to try and bury like Katy [Perry] ETC but I’m not that guy, sorry. I won’t allow it.”

Taylor later referenced Harris in her "Look What You Made Me Do" video—she crawls out of a graveyard next to a headstone that reads "Nils Sjoberg," which was the fake name she used for “This Is What You Came For” songwriting credits.

The photos from Taylor and Harry's Central Park stroll will go down in history as the hipster moment. Taylor and Harry dated very briefly in late 2012–early 2013. The infamous photos were released on December 2, 2012, per E! News.

Even Harry has the day burned in his memory. “When I see photos from that day I think: Relationships are hard, at any age. And adding in that you don’t really understand exactly how it works when you’re 18, trying to navigate all that stuff didn’t make it easier,” Harry later told Rolling Stone in 2017. "I mean, you’re a little bit awkward to begin with. You’re on a date with someone you really like. It should be that simple, right? It was a learning experience for sure. But at the heart of it–I just wanted it to be a normal date.”

Although the relationship ended on rocky terms (Taylor may or may not have called Harry out at the 2013 VMAs), it seems Harry and Taylor now get along quite well. Women's Health even discussed it with an expert. They regularly meet up at awards shows, and Taylor even gave Harry a standing ovation when he won Album of The Year at the Grammys in March 2023.

Taylor dated 18-year-old Conor Kennedy for several months in 2012 (she was 23 at the time), and clearly she won over his legendary family. Conor’s grandmother Ethel Kennedy later told People that Taylor “is just spectacular. She’s just sensational inside and out.”

A source told People that Taylor was “head over heels into” Conor, adding, “[She] is on cloud nine...She thinks she is in love.”

Taylor even bought a $4.9 million house in Cape Cod to be closer to Conor and his family, the New York Daily News reported. (She eventually sold the property just three months later, per The Cape Cod Times.) Sources told Us Weekly that it ended amicably in October 2012. "It was just a distance thing. No hard feelings. They're fine," one source said.

Taylor later penned Red's "Starlight" based on stories she heard from the Kennedy family, but it doesn't seem like her relationship with Conor left any lasting impressions—at least in the songwriting department.

If you're a dedicated Swiftie, you already know where this is going. Fans were surprised when Taylor was spotted strolling through the streets of Brooklyn with her arm around Jake Gyllenhaal in 2010. A source told Us Weekly that “it’s definitely serious.”

Sadly, their relationship took a pretty bad turn and they broke up by January 2011, per US Weekly. Taylor penned quite a few songs about Gyllenhaal, and he's seemingly the muse behind her most devastating album, Red, which includes tracks like "The Last Time," "We Are Never Ever Getting Back Together," and "All Too Well."

"'All Too Well' was the hardest to write because it took me a long time to filter through everything I wanted to say," Taylor told Good Morning America in 2010. "It started out being a 10-minute song, which you can't put on an album. I had to filter it down to a story that could work in the form of a song."

However, Taylor rerecorded the Red album and released the full 10-minute song with never-before-heard lyrics that further hinted at her fall-out with Jake, per The Washington Post.

"All Too Well (10 Minute Version)(Taylor's Version)" includes a paired music video (or short film) starring Stranger Things' Sadie Sink and it details exactly how Taylor felt about this tumultuous relationship.

Taylor also revealed some details of the pair's relationship to the press back when she was promoting Red for the first time: In 2012, Taylor told NPR that Jake was an "unreliable guy" but she's since let her work speak for itself.

2010 was a rough year for Taylor! John and Taylor got together in summer 2010 and dated for a few months, but it didn’t end well. Taylor later implied that John could have been a lot nicer to her in a song titled “Dear John.”

"Don't you think I was too young to be messed with? / The girl in the dress cried the whole way home. I should've known,” she wrote in the lyrics.

John later told Rolling Stone that Taylor’s song “humiliated” him, and hasn't publicly spoken very kindly about Taylor since.

“I never got an e-mail. I never got a phone call,” he told Rolling Stone. “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?”

John later released a diss track of his own in 2013, "Paper Doll" which includes the lyrics "You're like 22 girls in one / And none of them know what they're running from / Was it just too far to fall for a little paper doll?"

He's never admitted forthright that the song is about Taylor, but the "22" seems pretty telling to me.

Taylor got the last laugh, though. In 2022, Taylor released the bonus track “Would’ve, Could’ve, Should’ve” on her new album Midnights, and it rehashes what went down between the two singers way back when, Page Six reported.

“At 19, and the God’s honest truth is that the pain was heaven/ And now that I’m grown, I’m scared of ghosts/ Memories feel like weapons/ And now that I know, I wish you left me wondering,” the now 33-year-old musician sings. Taylor even says in the song's most devastating lyric: "Give me back my girlhood, it was mine first."

In response to the new song, Swifties turned to Twitter to call John Mayer out for how he treated her. “John Mayer, be scared,” tweeted one user. "John mayer you better start running,” wrote another, per Page Six. With Speak Now (Taylor's Version) on its way, John Mayer has yet another reason to start running: "Dear John (Taylor's Version)."

Taylor met Twilight star Taylor Lautner on the set of Valentine’s Day. They reportedly dated between August and December 2009. Lautner later told Entertainment Tonight that “It was a good time. It was a fun few months there...”

Years later, Lea Michele and John Stamos later grilled Lautner about the romance on Facebook Live and he had nothing but great things to say about his ex. “It's like, Taylor's the nicest,” he said in 2016.

Taylor Swift pretty obviously wrote the single "Back To December” about her ex, apologizing for a rough night and seemingly regretting the breakup. "I miss your tan skin, your sweet smile," she wrote, along with, "It turns out freedom ain't nothing but missing you," and "wishing I'd realized what I had when you were mine."

It seems a song from Midnights might be Taylor Lautner-inspired, too. "Midnight Rain" details Taylor breaking up with someone who didn't really deserve it, and who later ends up with someone else. Lautner recently got married to Taylor Dome in 2022.

"I broke his heart 'cause he was nice," Taylor sings in "Midnight Rain," and later, "He wanted a bride I was making my own name, chasing that fame / He stayed the same / All of me changed like midnight rain."

Ah, yes. The original Taylor Swift Boyfriend. Joe J and Taylor dated for a few months back in 2008, but they broke up in October of that year. "We were children," Joe told Andy Cohen in 2016, per ET. "We were 18, 19. Young enough."

Taylor infamously went on The Ellen DeGeneres Show in 2008 and said Joe dumped her during a phone call that lasted less than a minute. “You know what it's like, when I find that person that is right for me, he'll be wonderful...When I look at that person, I'm not even going to remember the boy who broke up with me over the phone in 25 seconds when I was 18,” she said.

Taylor penned her Fearless track "Forever and Always," about Joe. "[It's] a song about watching somebody completely fade away in a relationship and wondering what you did wrong," she told People.

But that's not the only song to come out of the relationship. The Jonas Brothers track "Much Better" also seems Taylor-inspired: "I get a rep for breakin' hearts / Now I'm done with superstars / And all the tears on her guitar."

Now, Joe J. and Taylor get along swimmingly. On a much-later Ellen episode in 2019, she admitted she shouldn't have talked about their break up on air during the show's "Burning Questions" segment. She said the 2008 interview was the most rebellious thing she did as a teenager. "That was too much," she said of the moment in 2019. "[Joe and I] laugh about it now."

At a Jonas Brothers concert in 2022, Joe changed the "Much Better" lyrics to "Now I'm cool with superstars," per Billboard.

Taylor's songs "Mr. Perfectly Fine" and "Better Than Revenge" are also rumored to have been inspired by the JoBro, per Distractify. There are even some lyrics in her song "invisible string" that seem to be a callback to her relationship with Joe.

"Cold was the steel of my axe to grind / For the boys who broke my heart / Now I sent their babies presents."

It was rumored that Taylor may have sent Joe and Sophie Turner, Joe Jonas' wife, a gift, as the couple welcomed their daughter, Willa, shortly before "invisible string" was released in 2020.