From Joe Jonas to a Quick Fling With Matty Healy, Everyone Taylor Swift Has Dated Through the Years

When: July 2008 — October 2008

Swift's first highly publicized relationship was with the Jonas Brothers singer. The pair dated for a few months before Swift famously told Ellen DeGeneres that he broke up with her over a 27-second phone call. Swift responded by writing the breakup songs "Last Kiss" and "Forever and Always" about him, but things got even more strained between them when Jonas went on to date actress Camilla Belle. Swift penned a fiery tune called "Better Than Revenge," which includes lyrics aimed at Belle like, "She's an actress / But she's better known / For the things that she does on the mattress."

Per People, Jonas later spoke out about the breakup in a MySpace post that read:

"Several things I will state with all my heart. I never cheated on a girlfriend. It might make someone feel better to assume or imply I have been unfaithful but it is simply not true. Maybe there were reasons for a breakup. Maybe the heart moved on. Perhaps feelings changed. I am truly saddened that anything would potentially cause you to think less of me."

It looks like the phrase "time heals all wounds" is true, though, because the exes were eventually able to bury the hatchet. During a 2019 appearance on "The Ellen DeGeneres Show," Swift admitted that she regrets putting Jonas "on blast."

When: March 2009 — April 2009

Sparks apparently flew between Till and Swift when he costarred in her "You Belong With Me" music video, but their romance was short-lived. In an interview with MTV, Till revealed his reason behind why they couldn't make things work. "We dated for a little bit, but there was no friction because we were too nice," he explained. "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."

When: August 2009 — December 2009

After playing boyfriend and girlfriend in the 2010 rom-com "Valentine's Day," these two Taylors started dating for real. Although their relationship earned one of Hollywood's cutest nicknames, "Taylor Squared," a source close to the then-country singer told People, "They went out on a few dates and realized this was just not going anywhere." The sad song "Back to December" off of Swift's "Speak Now" album is reportedly about the "Twilight" star, which expresses regret for how she ended things with him and has lyrics referencing his "tan skin" and "sweet smile."

When: December 2009 — February 2010

Swift was romantically linked to Mayer when they collaborated on his song "Half of My Heart," but things between the couple quickly soured. Swift entitled the breakup song "Dear John" about him, which clearly didn't hide who it was about. With lyrics like "Dear John, I see it all, now it was wrong / Don't you think 19 is too young to be played by your dark twisted games, when I loved you so?" the "Daughters" singer was none too pleased.

"It made me feel terrible, because I didn't deserve it," he told Rolling Stone in a 2012 interview. "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."

When: October 2010 — January 2011

Gyllenhaal and Swift began quietly dating and sharing maple lattes together in the fall of 2010, and per Marie Claire, it was rumored Gyllenhaal was so enchanted by her that he dropped $160,000 just so he could fly her in on a private jet for a date. Talk about getting bit by the love bug, huh?

By New Year's Eve, however, Gyllenhaal and Swift had gone their separate ways. Swift got all of her emotions about their relationship out in "All Too Well," with lyrics like, "Oh, your sweet disposition and my wide-eyed gaze / We're singing in the car, getting lost upstate / The autumn leaves falling down like pieces into place, and I can picture it after all these days."

In 2021, Swift released a 10-minute version of "All Too Well" along with a short film starring Sadie Sink that provided even more details about their relationship's emotional conclusion.

Neither Swift or Gyllenhaal have ever directly confirmed the song is about their romance, but after the long version's release, Swift's fans flocked to his social media to criticize him, so much that he had to turn off comments on his Instagram. "It has nothing to do with me. It's about her relationship with her fans," he told Esquire in February. "It is her expression. Artists tap into personal experiences for inspiration, and I don't begrudge anyone that."

When: July 2012 — October 2012

Kennedy struck up an intense summer romance with Swift in 2012, which started that July when, per E! News, they were first spotted together sharing lunch at a pizza place in Mount Kisco, NY. The rest of that summer was filled with plenty more supercute, supercouple-y activities between the two, like making out at his family's estate in Hyannis Port, MA, and splashing around in the ocean. It started to look like things between Swift and Kennedy weren't going so well when his family accused Swift of crashing the wedding of Kennedy's cousin Kyle in August, according to E! Her reps denied it, but it appeared the damage had been done. As the warmer months cooled off, so did Swift and Conor's relationship. They split by October.

When: March 2015 — June 2016

Swift first met Scottish DJ Harris when mutual friend Ellie Goulding introduced them at the Elle Style Awards in February 2015. By March, they were inseparable. With their romance clocking in at just over a year, the two went on a number of cute dinner dates and packed in plenty of award-show PDA. Although Harris and Swift had heaps of nice things to say about each other, they broke up not long after celebrating their one-year anniversary and just shortly after Harris got into a car crash.

Their split seemed to be amicable at first, but when Swift was seen kissing Tom Hiddleston two weeks after breaking things off with Harris, the DJ was left "hurt" and "blindsided," according to sources. Per Vanity Fair, Harris took down the tweet he posted that asserted their breakup was full of "respect" and "love," and he also claimed in a series of tweets that Swift's team was deliberately trying to make him look bad after it was revealed Swift wrote Harris's hit song "This Is What You Came For." He eventually opened up about his social media rant, saying he just "snapped."

When: Probably the end of 2016 — March 2023

After splitting from Hiddleston (and having a reignited feud with Kim Kardashian and Kanye West), Swift disappeared almost entirely from the spotlight. She was no longer active on social media, she didn't attend any events, and there were virtually no paparazzi photos of her. But while she laid low professionally, her romantic life was heating up again.

News broke in May 2017 that Swift was dating English actor Alwyn and that their under-the-radar romance had been going on for months. In one of the deluxe versions of "Lover," Swift alluded that they officially started dating sometime around late September/early October 2016. They went on to keep their romance pretty much under the radar from that point on. But Swift did give Alwyn a shout-out during her acceptance speech at the Grammys in 2021. "Joe, who 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.

They continued to stay quiet, but Swift also acknowledged him in an Instagram video promoting a song on her new album, "Midnights," called "Lavender Haze." "If the world finds out that you're in love with somebody, they're gonna weigh in on it," she said. "Like my relationship for six years, we've had to dodge weird rumors, tabloid stuff, and we just ignore it. And so this song is sort of about the act of ignoring that stuff to protect the real stuff."

As Swift kicked off her Eras Tour, a source told People that Alwyn "will travel with her when he can." However, on April 7, People confirmed that Swift and Alwyn had split after six years of dating.

A source told Entertainment Tonight that their split "was not dramatic." They added "the relationship had just run its course. It's why [Alwyn] hasn't been spotted at any shows."

Related:

2020-2022: Taylor Swift and Joe Alwyn Dodge Engagement Rumors

When: May 2023 - June 2023

Shortly after Swift's breakup from Alwyn was made public, rumors began swirling that Swift was seeing Matty Healy, the first reports originating from The Sun on May 4. A day later, The 1975 lead singer was spotted attending Swift's Eras Tour concert in Nashville. While there was some debate among fans about whether or not Healy and Swift were just hanging out as friends or dating, things seemingly moved firmly into romantic territory when the musicians were photographed by a fan holding hands at a restaurant in New York City on May 11.

Swift and Healy are actually longtime friends, with rumors that they dated going all the way back to 2014 when Swift was once spotted wearing a The 1975 t-shirt (they're pictured together here having fun at the 2015 Brits afterparty).

In 2016, Healy squashed dating rumors after he courted controversy for telling Q Magazine that March that he would find being Swift's boyfriend "emasculating." In a May 2016 tweet addressing the controversy (via Yahoo), he wrote, "I didn't even date Taylor, but the media's incessant and brutal obsession with her has meant that even a guy who DIDN'T DATE HER has been so battered by their never-ending questions that he's inevitably said something that can be lifted and moulded into something that resembles 'shade.' It's really sad."

Swift and Healy have yet to address their latest dating rumors publicly, but it seems whatever was on is now off. On June 5, multiple outlets reported that Swift and Healy's romance had fizzled out.