To date Taylor Swift is to essentially guarantee that you will be immortalized in one of her albums. From her first high-profile boyfriend at 18, the singer has relied on a never-ending string of romantic relationships to inform her songwriting. Check out our timeline of Taylor Swift’s unique and extensive dating history that matches her exes to her hit songs.
Taylor dated Joe Jonas in the summer of 2008, but things were over by fall. Still, the relationship remains infamous because of its cruel and cold end. In a November 2008 appearance on Ellen, Taylor explained, “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 went on to write three songs about Jonas: “Last Kiss”, “Better Than Revenge,” and “Forever and Always,” the last of which asks her ex, “Was I out of line? Did I say something way too honest, made you run and hide like a scared little boy?”
One year later, while hosting Saturday Night Live, Taylor apparently still held a grudge. “You might think I’d bring up Joe, that guy who broke up with me on the phone,” she sang. “But I’m not going to mention him in my monologue. Hey Joe! I’m doing real well and I’m hosting SNL—but I’m not going to write about that in my monologue.”
But a lot can change in a decade. In May 2019, Taylor returned to Ellen. During a segment called “Burning Questions,” DeGeneres asked her guest to name the most rebellious thing she did as a teenager.
“Probably when I put Joe Jonas on blast on your show,” Swift said. “That was too much… We laugh about it now but that was some mouthy—yeah, just some teenage stuff there.”
That’s not to say she doesn’t still rely on their short-lived romance for material. Fans suspect that the song “Invisible String” on her 2020 album Folklore is about Jonas. “Cold was the steel of my axe to grind / For the boys who broke my heart,” sings Swift. “Now I send their babies presents / Gold was the color of the leaves / When I showed you around Centennial Park / Hell was the journey but it brought me heaven.”
In March 2009, Taylor briefly dated actor Lucas Till. The two met on the set of Hannah Montana: The Movie, but the flame flickered out after just one month.
“We dated for a little bit. But, there was no friction because we were too nice,” Till told MTV News in 2019. “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.”
Till managed to escape the relationship unscathed. While there don’t seem to be any songs written about him, he did manage to nab a spot in the music video for her song, “You Belong With Me.”
August 2009 marked the birth of Taylor Squared—a five month-long period where Swift was linked to Twilight star, Taylor Lautner. The two met on the set of the 2010 rom-com Valentine’s Day, in which they play high school sweethearts.
Their attempt at a real-life romance didn’t last very long, but sources say that neither shed tears over it.
“The media made way more out of it than it is,” a source close to Swift told People. “They went out on a few dates and realized this was just not going anywhere.”
“They became good friends and then went out a few times, but he lives in L.A. and she lives in Nashville and their busy schedules kept it from becoming more than it was,” a source close to Lautner added.
Taylor reflected on their time together in “Back to December,” off of her 2010 album Speak Now. “You gave me roses and I left them there to die,” she sings. “So this is me swallowing my pride / Standing in front of you saying I’m sorry for that night / And I go back to December all the time.”
From December 2009 to February 2010, Taylor dated fellow singer-songwriter John Mayer.
The two forged a bond over music, with Taylor collaborating on “Half of My Heart” for Mayer’s 2009 album Battle Studies.
But perhaps their age difference—Mayer is 15 years her senior—is something they couldn’t overcome. In “Dear John,” she sings, “Dear John, I see it all, now it was wrong / Don’t you think nineteen is too young /To be played by your dark twisted games, when I loved you so? / I should’ve known.”
In October 2010, actor Jake Gyllenhaal entered Taylor’s life. Things intensified at warp speed, with Gyllenhaal reportedly spending $160,000 to fly her on a private jet for a date in London. It was quite a splurge for a romance that lasted all of three months.
And Gyllenhaal is still paying the price for it in other ways. In a tense 2017 interview with The Guardian, the actor repeatedly shuts down questions regarding Swift. “I would love to not talk about my personal life,” he said.
Meanwhile, Swift predictably worked through her feelings by writing 2012’s Red. “I look back on this as my only true break up album,” she said in a Rolling Stone podcast. “Every other album has flickers of different things–this was an album that I wrote specifically about a pure, absolute, to the core heartbreak.”
In “All Too Well” Swift sings, “Left my scarf there at your sister’s house / And you still got it in your drawer even now.” Fans are convinced this is a reference to a paparazzi photo where Taylor and Gyllenhaal are seen walking arm in arm while she dons a striped scarf. (When asked if it’s still at her place, actress Maggie Gyllenhaal said, “It’s totally possible. I don’t know.”)
“We Are Never Ever Getting Back Together,” “State of Grace,” and “The Moment I Knew” are also rumored to be about Gyllenhaal.
From July through October 2012, Taylor was romanced by Conor Kennedy, grandson of Robert F. Kennedy. It all started when word got out that “Starlight,” off of Red, was inspired by the relationship between Bobby and Ethel Kennedy. Rory, Ethel’s daughter, reached out to Taylor and gave her entry into the famed family’s world.
Unfortunately, rumor has it some of Kennedy’s blue blood relatives weren’t too keen on the musician. In August, when Taylor showed up at the wedding of one of Conor’s relatives, the mother of the bride asked her to leave. “I personally went up to Ms. Swift, whose entrance distracted the entire event, politely introduced myself to her, and asked her as nicely as I could to leave,” Vicki Kennedy told the Boston Herald. “It was like talking to a ghost. She seemed to look right past me.”
Some believe a line in the song “Begin Again” (“I think it’s strange that you think I’m funny ’cause he never did”) is a reference to Conor.
But just after the new year, while on holiday in the British Virgin Islands, the couple reportedly had a blowout fight and Taylor made a solo journey back to Nashville.
Taylor drew on the experience for songs on 1989. In “All You Had to Do Was Stay,” she sings, “Had me in the palm of your hand / Then, why’d you have to go and lock me out when I let you in”
From March 2015 to June 2016, Taylor dated superstar DJ Calvin Harris. The two were introduced by Ellie Goulding at the 2015 Elle Style Awards and were attached at the hip from that moment on.
Harris, triggered by Taylor’s new relationship with Tom Hiddleston, went on a since-deleted Tweet rampage.
“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 wrote.
Theories are abundant when it comes to Taylor’s 2019 album Lover. “I Forgot That You Existed” and “I Did Something Bad” are allegedly about Harris, if not—believe it or not—Kanye West. Others believe “Dancing With Our Hands Tied,” in which Swift sings about an invisible locket, is about the end of her time with Harris (who once gifted her with a locket).
Between June and September 2016, Taylor was linked with Avengers star Tom Hiddleston. That’s right—she fell into his arms only weeks after her split with Harris. The two hit off at the Met Gala that year, but after only a few months, Taylor was suspicious about Hiddleston’s motives. An insider told DailyMail.com the singer felt super “uncomfortable” over his desire to be “so public” with their romance. Was it all just a publicity stunt?
Swift addressed Hiddleston in “Getaway Car,” suggesting that she used him as an excuse to leave Harris (ouch). She sings, “It was the best of times, the worst of crimes / I struck a match and blew your mind / But I didn’t mean it / And you didn’t see it / The ties were black, the lies were white / In shades of grey in candlelight / I wanted to leave him / I needed a reason.”
Rumors that Taylor was dating her current boyfriend, English actor Joe Alwyn, began around May 2017.
“This isn’t a new couple alert or a secret relationship – the only people this has been a secret to is the media,” a source told The Sun. “After her 1989 tour and all the attention Taylor received, she learned she had to be more protective of her personal life and she and Joe decided early on to keep their private life private.”
In October, at a secret listening session for her album Reputation, Swift told a crowd of 300 attendees that the track “Gorgeous” was about Alwyn.
Almost a year later, the couple was still managing to keep a low profile. “I’m aware people want to know about that side of things,” Alwyn told British Vogue, “…but I really prefer to talk about work.”
This November, Taylor finally revealed some thoughts about the relationship. In an interview with Paul McCartney for Rolling Stone, she praises the music icon for successfully separating fame from his personal life.
“I know you have done a really excellent job of this in your personal life: carving out a human life within a public life, and how scary that can be when you do fall in love and you meet someone, especially if you’ve met someone who has a very grounded, normal way of living,” said Swift.
“I think that in knowing him and being in the relationship I am in now, I have definitely made decisions that have made my life feel more like a real life and less like just a storyline to be commented on in tabloids,” she added.