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Fans of Taylor Swift are as interested in her love life as they are in her music, in part because so much of her discography is dedicated to what she has learned and experienced in love.
Swift has often sung about previous boyfriends without naming them, along with the public’s reaction to her dating in the spotlight. In music videos, she has included a couple easter eggs that pay homage to her partners that fans and outlets alike have identified and shared.
While Swift has gotten more private about her romantic connections in recent years, particularly during her six years dating Joe Alwyn, people are always curious about the lucky few who have earned a place in her heart—and sometimes in her lyrics, too.
Below is everything we know about who Swift has dated.
Joe Jonas: 2008
As pop royalty in the late aughts, Joe Jonas and Taylor Swift crossed paths frequently. While her friend Selena Gomez briefly dated Nick Jonas, Swift paired off with Joe in 2008. They dated for about three months, but Swift was hurt when he broke things off in a phone call that lasted less than 30 seconds in October of that year. She allegedly wrote a number of songs about that relationship that ended up on her second album, Fearless, including “Forever & Always,” “Last Kiss,” “Better Than Revenge,” and “Mr. Perfectly Fine.”
On the Ellen DeGeneres Show a month after their break up, Swift said, “It’s all right, I’m cool...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 explained, “I looked at the call long—it was like 27 seconds. That’s got to be a record.”
In 2019, Swift was on DeGeneres’ show again and walked back her comments a bit when asked about her “most rebellious” act.
“Probably when I, like, put Joe Jonas on blast on your show,” she told the host. “That was too much. That was too much. I was 18. Yeah. We laugh about it now, but … that was mouthy. Just some teenage stuff there.”
They did indeed seem to have a friendly relationship almost 15 years later, but when the news broke that Joe Jonas was divorcing wife Sophie Turner, Swift offered her support to Turner. The Game of Thrones star reportedly stayed in Swift's NYC apartment as she worked out custody with her former partner.
Lucas Till: 2009
Lucas Till starred as the love interest in Swift’s music video for “You Belong With Me” in 2009, but they’d known one another for a bit. Swift had a cameo in Hannah Montana: The Movie, and Till was in the film as well. They split up after a few months with seemingly no drama.
“We dated for a little bit. But there was no friction because we were too nice,” he told MTV at the time. “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 Lautner: 2009
In the film Valentine’s Day, the two Taylors played love interests, and they ended up having real-life chemistry, dating in the fall of 2009. After they broke up, Swift supposedly wrote “Back to December” for Lautner, a song that implies she dumped him. He later said of her writing about their relationship, “That’s just what she does.”
After their breakup, Swift told Glamour, “He’s one of my best friends. He’s wonderful, and we’ll always be close. I’m so thankful for that.”
They really did maintain a friendship, and in 2023, Lautner starred in the music video for her song “I Can See You,” then appeared on stage at a concert during her Eras Tour.
While on stage, Lautner addressed Swift, saying, “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.”
Corey Monteith: 2010
Glee's Corey Monteith and Swift dated for about a month. It’s believed her song “Mine” is about Monteith, and it highlights how little she knew about the late star.
After his passing in July 2013, Swift wrote in a tweet that has since been deleted, “Speechless. And for the worst reason.”
John Mayer: 2009-2010
Swift and musician John Mayer collaborated on the latter’s song “Half of My Heart” and then dated for a few months. He was 32 years old, and she was 20, and Swift later seemed to comment on their age gap in her song “Dear John.”
“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,” Swift says in the lyrics.
Mayer did not respond well to the song.
“It made me feel terrible,” Mayer told Rolling Stone in 2012. “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.”
Mayer himself had been criticized around that time for how he discussed exes Jessica Simpson and Jennifer Aniston in the press, and said he entered a period of self-reflection and felt Swift was “kicking him while he was down.”
“I will say as a songwriter that I think it’s kind of cheap songwriting,” he added. “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.”
When the song was re-recorded in 2023 for Speak Now (Taylor's Version), controversy around these old comments sprang up again, and Swift ended up making a statement to discourage her fans from going after Mayer.
“I'm 33 years old. I don’t care about anything that happened to me when I was 19,” she said while on stage before performing the song. “I'm not putting this album out so that you can go and should feel the need to defend me on the internet against someone you think I might have written a song about 14 billion years ago.”
Jake Gyllenhaal: 2010
In another big age gap relationship from 2010, 20-year-old Swift dated actor Jake Gyllenhaal, who was 29 at the time. Gyllenhaal allegedly broke up with her via text, citing the age difference as a problem. But it seemed like he might have been a bit hot-and-cold according to a source speaking with Us Weekly at the time.
“Jake reached out to her and started all of this, but now he’s not acting as interested,” said the insider. “He said he wasn’t feeling it anymore and was uncomfortable with all the attention they got. Taylor is really upset. We told her not to move so fast with this, but she didn’t listen.”
They added, “Jake cares about her, but [the publicity] was a lot for him. He wants to keep his private life private, and that’s hard to do dating Taylor.”
Swift and Gyllenhaal were together for three months, and it’s believed he inspired her songs “We Are Never Getting Back Together,” “State of Grace,” and “The Moment I Knew.”
But, most famously, he appears to be the subject of “All Too Well,” which Swift re-recorded for her re-release of Red (Taylor’s Version). Swift directed a 10-minute long music video for the song starring Stranger Things’ Sadie Sink as a young woman dating a guy who appears to be a stand-in for the Brokeback Mountain star.
Conor Kennedy: 2012
Swift dated Robert F. Kennedy’s grandson, Conor Kennedy, in 2012 for a few months. She also wrote a song released that same year about Robert Kennedy and his wife Ethel called “Starlight.”
While they dated, Swift bought a home near the Kennedy compound in Hyannis Port, Massachusetts, and she befriended Ethel. Their relationship drew strange attention, including a rumor she had “kidnapped” him, according to an interview with Rolling Stone.
“You can't kidnap a grown man!” she refuted the claim. “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.”
Harry Styles: 2012
Harry Styles and Swift were first seen together in November 2012, and fans of One Direction went wild. They broke up after three months, with paparazzi photos showing Swift leaving their vacation in the British Virgin Islands alone on a boat.
An insider speaking with Vanity Fair in 2013 stated that Styles initially pursued Swift and “wore her down.”
“He was all, like, “You’re amazing—I want to be with you. I want to do this,’” the source said.
They then alleged that Swift believed Styles was seeing other people or at least had a wandering eye. They broke up, then got back together.
“But the whole time she says she feels like he’s looking at every girl,” the insider continued. They added that one evening in London, Styles fell off the map, and when they saw each other again, “it was like he just didn’t want to keep going.”
A rep for Styles called the claims “undeniably false” at the time.
Three songs about Styles are supposed to be on her album 1989, “Out of the Woods,” “Style,” and “I Knew You Were Trouble.” In her music video for the first song, fans believe Swift left a number of easter eggs referencing the relationship, including her choice to wear a blue dress resembling the one she wore in the pics of her island departure.
Calvin Harris: 2015-2016
Starting in March 2015, Swift was seen with Scottish DJ Calvin Harris, née Adam Richard Wiles. They went red carpet official at the Billboard Music Awards a few months later and dated for about a year. Harris supposedly broke things off, and they both ended up wiping their social media accounts of evidence of their relationship.
A source told People that Harris was “intimidated” by her success.
“[Harris] said on multiple occasions that he was intimidated by Taylor, which is why he would not attend any events where she was being honored, or any award shows unless he was nominated,” they said.
Another source claimed they were from “different worlds” and the 5-year age gap made it even harder.
“Taylor somewhat lacks real-life experience,” the source explained. “They will not be getting back together.”
A day after their break up came out, Harris wrote in a now deleted tweet, “The only truth here is that a relationship came to an end & what remains is a huge amount of love and respect.”
Swift retweeted it.
Tom Hiddleston: 2016
In June, Tom Hiddleston and Swift started dating after rumors swirled following their meet up at the 2016 Met Gala. Hiddleston was seen with Swift and some of her “squad” on Rhode Island soon afte,r and pictures of the day went viral after he wore a T-shirt reading, “I Heart T.S.”
Because of the attention they received and how quickly they got together following her split with Harris, they were accused of creating a PR relationship, which Hiddleston has denied.
“Taylor is an amazing woman. She’s generous and kind and lovely, and we had the best time,” he told GQ in February 2017. “Of course, it was real.”
They split up in September after three months together. A source said Hiddleston was too public for Swift.
“She was the one to put the brakes on the relationship,” they told Us Weekly. “Tom wanted the relationship to be more public than she was comfortable with. Taylor knew the backlash that comes with public displays of affection, but Tom didn’t listen to her concerns when she brought them up.”
They added that Hiddleston was “embarrassed that the relationship fizzled out.”
Joe Alwyn: 2016-2023
Swift’s longest known relationship followed shortly after. She also met Alwyn at the Met Gala, but no one knew they were together until 2017. She and the actor were fairly private about their relationship throughout it, which might have contributed to its longevity.
In her 2020 documentary Miss Americana, Swift said, “I was falling in love with someone who had a wonderfully normal, balanced life...We decided together we wanted our relationship to be private. I was happy. But I wasn’t happy in the way I was trained to be happy. It was happiness without anyone else’s input. We were just happy.”
A lot of songs are supposed to be about Alwyn, particularly on her albums Reputation and Lover, and he is even credited on her 2020 albums Folklore and Evermore. But before her album Midnights was released, she talked explicitly about him inspiring her song “Lavender Haze.”
“Like my relationship for six years, we've had to dodge weird rumors, tabloid stuff, and we just ignore it,” Swift said at the time. “And so this song is sort of about the act of ignoring that stuff to protect the real stuff.”
The former couple split in early 2023, and soon after Swift released “You're Losing Me,” which seemed to detail the reasons for their breakup. Basically, they grew apart and had different ideas about fame and public life.
But sources said part of the issue was they had grown differently, and there was a huge shift in their relationship when the pandemic lockdown ended, and Swift became for active in public again.
“They had plenty in common and fell in love in a safe bubble while she was retreating from the world during Reputation,” they said. “Then the pandemic hit, and they were locked down together and able to continue growing their relationship in this insulated way. But he didn’t really ‘know’ her yet outside of that bubble.”
They added, “Joe has struggled with Taylor’s level of fame and the attention from the public. The differences in their personalities have also become harder to ignore after years together. They’ve grown apart.”
Matt Healy: 2014 and 2023
In 2014, rumors circulated that Swift was dating The 1975 frontman Matt Healy, but it quickly petered out. Soon after she and Alwyn split, Healy and Swift started spending a lot of time together with him even making a few appearances at her Eras Tour in Nashville and Philadelphia. The romance seemed to burn bright and hot and burned out in a month.
When they broke up, it seemed like Swift just wasn’t ready for anything serious right after Alwyn.
“She had fun with him, but it was always casual,” a source told People. “They are no longer romantically involved.”
They added, “They were never boyfriend-girlfriend or exclusive and were always just having fun. There is no drama, and who knows what could happen again. It was a good time and ran its course.”
Travis Kelce: 2023
NFL star Travis Kelce shared that he tried to link up with Swift while at her concert in Kansas City, Missouri, in July, and a few months later, it looked like she got the message and made a meetup happen. In September, Swift was seen at a Chiefs game at Arrowhead Stadium alongside Kelce’s mother in the VIP box. Photos also circulated of her with her arm around his neck at an after-party.
A source told Entertainment Tonight in late September that they’re just getting to know one another, but it has been a surprisingly fast connection.
“When Taylor and Travis first connected, Taylor was looking to have fun while enjoying some downtime,” the source said. “So far, it’s been a nice change of pace for her. Now, as things progress between Taylor and Travis, they’re both looking to keep it more private. They’re both excited about where things are headed.”
In mid-October, a source told People that Swift and Kelce were giving dating an honest shot. “She’s the biggest star in the world, and it’s no secret dating an athlete is very tough, but they’ve been texting and talking on the phone between the pockets of time they get to spend with each other,” the source said.
“There’s not some looming date like, ‘Oh, she's going back on tour’ and ‘his football schedule is getting crazy.’ They’ll figure it out,” the source continued. “He’s said it himself, he knows what he signed up for with this attention, but they’ve spent time under the radar too. They’re giving things a real try.”
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