Taylor Swift's Boyfriends: The 'Lover' Look Back

On Sept. 24, 2023, Swift showed up to Arrowhead Stadium in Kansas City, Missouri, and went public with her romance with Travis Kelce by cheering for him and the Kansas City Chiefs. 

In 2024, the two rolled in as one of the biggest power couples in the world, with Kelce competing in his third Super Bowl and Swift earning her fourth Record of the Year at the GRAMMYs. 

For more on their romance, click here. 

The 1975 singer Matty Healy was first linked to Swift when he was spotted at the Nashville stop of her Eras Tour in May 2023, one month after news of her breakup from Alwyn first broke. The duo, who have been longtime friends, was later photographed together as well. 

"Taylor and Matty like each other," a source told ET shortly thereafter. "Taylor has a crush on Matty and they are having a good time hanging out. Matty also thinks Taylor is awesome and incredibly talented, too. They dated briefly in the past."

By June, though, the romance had ended. "Taylor and Matty broke up," a source told ET. "They are both extremely busy and realized they're not really compatible with each other. Taylor's friends want what's best for her and aren't shocked that their relationship fizzled out since she recently got out of a long-term relationship."

Her relationship with the actor was perhaps the one she kept the most private, with very little PDA and no Instagram or red carpet official moments. It's also not known when they started dating, but the pair were both at the 2016 Met Gala and were also at a Kings of Leon concert in New York City that October. 

On April 8, 2023, ET confirmed that after several years of dating the two had called it quits. ET also learned that the split was amicable and "not dramatic."

"The relationship had just run its course. It's why [Alwyn] hasn't been spotted at any shows," said the source.

The two were first romantically linked in June 2016, when they were snapped kissing on a beach outside of her multi-million dollar home in Watch Hill, Rhode Island. That PDA-filled moment came just one month after Taylor and Tom had been spotted dancing at the Met Gala just days before her and Calvin Harris' breakup. By September, however, ET had confirmed that they broke up after three intense months together, which had even included meeting each others' parents. "It was an amicable split," our source said.

After celebrating their one-year anniversary in March 2016, the two called it quits just a few months later in June. Multiple reports claim that it was the Scottish music producer who broke up with Taylor after 15 months together. "Taylor and Adam had no big blowout fight, but the romance just was not there anymore for them. Adam is the one that ended it,” a source revealed to E! News. “It was all done in a very mature fashion. Taylor is pretty upset but they are still in communication." A few months later, Calvin got candid about the split for the first time with British GQ. "It's very difficult when something I consider so personal plays out very publicly," he said in the interview. "The aftermath of the relationship was way more heavily publicized than the relationship itself. When we were together, we were very careful for it not to be a media circus. She respected my feelings in that sense."

The "Look What You Made Me Do" songstress was linked to the One Direction singer from October 2012 to January 2013. Months before they reportedly had a fling in April 2012, Taylor is said to have written "I Knew You Were Trouble," about the British singer, and the post-split songs "Out of the Woods" and "Style," off her 2014 album, 1989, are supposedly about Harry. In 2017, the "Sign of the Times" singer got candid with Rolling Stone about what it was like to date the superstar, saying, "Certain things don’t work out. There’s a lot of things that can be right, and it’s still wrong."

Taylor dated Robert F. Kennedy's grandson during the summer of 2012. The singer even purchased a house near the Kennedy compound in Hyannis Port, Massachusetts, while they were together. Over the course of their short-lived relationship, Taylor got approval from Conor's grandmother, Ethel Kennedy, and had to clear up a very strange rumor that she may have kidnapped Conor. "You can't kidnap a grown man!" the GRAMMY winner insisted to Rolling Stone, adding, "The way I look at love is, you have to follow it and fall hard, if you fall hard. You have to forget about what everyone else thinks." Aah, young, ill-fated love!

These two briefly dated for a few months in an on-again/off-again fling that lasted from October 2010 into early 2011. It's rumored that several of the songs on the singer's Red album, including "We Are Never Ever Getting Back Together," were written about the actor, which meant he was peppered with many questions about their relationship over the years. Though he did open up to Howard Stern on the subject in 2015 -- admitting that "she's a beautiful girl" -- when he was asked semi-relentlessly about Taylor again by The Guardian, Jake got mum, explaining, “I would love to not talk about my personal life.”

Taylor and the late Glee star never confirmed that they dated, which would have been briefly in the spring of 2010. They were, however, photographed together a few times and the singer-songwriter blushed when asked on The Ellen DeGeneres Show if they had dated. When Cory died in July 2013, Taylor wrote in a since-deleted tweet, "Speechless. And for the worst reason."

The GRAMMY winners were romantically linked from late 2009 to early 2010, though John seemed to have an more amicable take on their split than Taylor did. The Pennsylania native's Speak Now track, "Dear John," is one of the only ones to so blatantly name drop -- in the title! -- and a trio of very cutting line states, "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." In 2012, John told Rolling Stone that the song made him "feel terrible," explaining, "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." A few years later, he would go on to praise her album, Reputation, calling it "a fine piece of work."

"The Taylors" dated from October to December 2009 and co-starred as high-school sweethearts in Garry Marshall's romantic comedy, Valentine's Day. Her song, "Back to December," off 2010's Speak Now album, is supposedly an apology to the Twilight star revolving around the night she broke up with him. A few years later, his Scream Queens co-stars, Lea Michele and John Stamos, attempted to get Taylor L. to talk about his ex during a group interview, but he told Michele he found it "hilarious" and brushed off the song about him as just "what she does."

The Hannah Montana Movie star briefly (and we mean briefly) became Taylor's leading man after starring as her next-door neighbor/BFF/boy she has a crush on in the 2009 music video for "You Belong With Me." The months-long relationship ran its course when Lucas realized they were better off as friends. "We dated for a little bit. But there was no friction because we were too nice," he told MTV that same year. "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."

Taylor went out with the middle JoBro from July to October 2008. The country crooner-turned-pop star would go on to famously slam Joe for his 25-second phone breakup with her, but during a May 2019 appearance on The Ellen DeGeneres Show, Taylor admitted she regretted some of the remarks she made about him and their split. "Probably when I, like, put Joe Jonas on blast on your show," she told the talk show host of her most rebellious act as a teenager. "That was too much, that was too much. I was 18... We laugh about it now, but that was mouthy, yeah, some teenage stuff there." Needless to say, Joe appreciated the apology. "It did feel nice," he said of Taylor's statement a couple of weeks later on ITV's Lorraine show. "It's something that I was probably feeling pretty bad about when I was younger, but, at the end of the day, I've moved on. I'm sure Taylor's moved on. It feels nice. We're all friends. It's all good. We were so young." As for where he lies in the mindfield of exes Taylor has written songs about, Speak Now's "Last Kiss" and Fearless' "Forever and Always" are said to be about Joe.