Taylor Swift’s love songs are about universal ideas. But knowing Swift’s dating history helps us understand the specifics: Her exes reportedly helped inspire some of the lyrics.
Throughout the singer songwriter’s years in the spotlight, she’s gone in and out of romantic relationships, some of which were memorialized in song form.
“I don’t talk about my personal life in great detail. I write about it in my songs, and I feel like you can share enough about your life in your music to let people know what you’re going through,” Swift told Glamour in 2012.
She said she will “never” confirm who songs are about — but fans have turned guessing into a past time. The song “All Too Well,” off “Red,” is believed to be about Jake Gyllenhaal, whom Swift dated when she was 20 and he was 29. Now, Swift frequently sings about her boyfriend, Joe Alwyn, whom she’s been dating since 2016 (See: “Lover,” “London Boy”).
But the era of Swift’s dating life-inspiring-music may be reaching an end. Swift’s recent albums, like “folklore” and “evermore,” seem to center on fictional characters. Now, as the countdown nears for Swift’s newest album “Midnights,” people are wondering, “Who’s she going to write about next?”
Read on for a brief refresh of Swift’s dating history — and the songs her exes inspired.
Joe Jonas (2008)
Swift dated Joe Jonas for about three months in 2008.
Although short-lived, Swift said in an interview on The Ellen DeGeneres Show in 2008 that their relationship sparked inspiration for a song on her album “Fearless.” She told Ellen that when the couple started to go downhill, she booked a last-minute studio session to record the song “Forever & Always.”
During the interview with Ellen, Swift also went into the specifics of their breakup. According to Swift, Jonas broke up with her over the phone.
“When I find that person who 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,” Swift said on the show.
While hosting Saturday Night Live in 2009, Swift mentioned her relationship with Jonas during her opening monologue.
“You might think I’d bring up Joe, that guy who broke up with me on the phone. But I’m not going to mention him in my monologue song,” she sang on SNL. “Hey Joe! I’m doing real well and I’m hosting SNL — but I’m not going to write about that in my monologue.”
Lucas Till (2009)
Lucas Till appeared in the music video for Swift’s “You Belong With Me.” Till told MTV in 2009 that they dated “for a little bit.”
“There was no friction because we were too nice. We just really both liked each other … 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,” he said.
Taylor Lautner (2009)
While Swift and “Twilight” star Taylor Lautner dated, fans referred to the couple as “Taylor Squared.” (Lautner is now engaged to another woman named Taylor).
Swift and Lautner first connected in the fall of 2009 while playing a couple in the romantic comedy “Valentine’s Day,” and broke up a few months after.
While brief, their relationship made it into a song. In 2016, during a Facebook Live Q&A, Lautner confirmed the song “Back to December” is about him.
In the song, Swift seems to express regret over the fallout of a relationship: “It turns out freedom ain’t nothin’ but missin’ you / Wishin’ I’d realized what I had when you were mine.”
John Mayer (2009 – 2010)
John Mayer and Swift met after collaborating on Mayer’s single “Half of My Heart” in 2009, and were romantically involved afterward.
While neither of them has specified the details of their relationship, Mayer told Rolling Stones in 2012 that he believed Swift’s song “Dear John” is about him.
In “Dear John,” Swift points to a couple’s age gap, which matches up with their relationship: She was 19 when she dated Mayer, who was 32. She sings, “Don’t you think I was too young to be messed with?” and later, “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?”
Speaking to Rolling Stone, Mayer called the song “humiliating.”
“It made me feel terrible. 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.”
In an interview with Glamour in 2012, Swift said that it was presumptuous for Mayer to believe the song was about him. “I never disclose who my songs are about,” Swift said to Glamour.
But when asked about the meaning of the song, which appeared on the best-selling 2010 album “Speak Now,” Swift said the lyrics resonated with many people.
“I think that song really hit home with a lot of girls who had been through toxic relationships and had found their way to the other side of it,” Swift said to Glamour. “I’ve never looked out while singing a song during a concert to see so many girls crying.”
Jake Gyllenhaal (2010)
Jake Gyllenhaal and Swift dated briefly in 2010. Since then, people have speculated whether or not Swift wrote the song “All Too Well,” about their relationship.
When Swift released a 10-minute-long remake for her new “Red (Taylor’s Version)” album in 2021, fans close-read lyrics for more proof of their connection to Gyllenhaal. “They say all’s well that ends well / but I’m in a new hell every time / You double-cross my mind,” Swift sings. “You said if we had been closer in age / maybe it would have been fine / And that made me want to die.”
In 2021, Gyllenhaal told Esquire that he doesn’t think the song concerns him.
“It has nothing to do with me. It’s about her relationship with her fans,” he told Esquire. “It is her expression. Artists tap into personal experiences for inspiration, and I don’t begrudge anyone that.”
Although lyrics in the song reference moments in couple’s relationship — including their age gap and going to Thanksgiving dinner at Gyllenhaal’s sister Maggie’s house — Swift has never confirmed that she wrote the song about him.
Conor Kennedy (2012)
Swift was linked to Conor Kennedy, Robert Kennedy’s grandson, in the summer of 2012. When asked about their relationship by Glamour in 2012, Swift responded that she doesn’t talk about her personal life in great detail.
But Kennedy’s well-documented family inspired the song “Starlight” on the album “Red.” Swift also told the Wall Street Journal in 2012 that she discovered a picture of Conor’s grandparents, Ethel Kennedy and Robert F. Kennedy, as teenagers in the 60’s.
“It immediately made me think of like how much fun they must have had that night,” Swift told the WSJ. “So I just kind of wrote that song from that place, not really knowing how they met or anything like that.”
Harry Styles (2012 – 2013)
Harry Styles, then performing with the boy band One Direction, met Swift at an award show in 2012, according to Rolling Stone. For their second date they went on a heavily photographed walk around Central Park.
Their relationship ended a few short months after, and the whirlwind romance has since been examined by members of Swift and Styles’ fanbases. They speculate Swift’s “Out of the Woods” and “Style” might be about him — among others.
Five years later, in 2017, Styles opened up about their relationship to Rolling Stone, and said he was surprised by photos of their date going viral.
“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,” Styles said. “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.”
As an artist himself, Styles said that he knows that musicians write songs about their personal experiences.
“I write from my experiences; everyone does that. I’m lucky if everything (we went through) helped create those songs,” Styles said in the interview. “That’s what hits your heart. That’s the stuff that’s hardest to say, and it’s the stuff I talk least about. That’s the part that’s about the two people. I’m never going to tell anybody everything.”
Calvin Harris (2015 – 2016)
Following photographs of them together, Swift and DJ Calvin Harris went public at the 2015 Billboard Music Awards, kissing at the ceremony.
Around the time of their one-year anniversary, Swift called their relationship “magical.”
“I’m just taking things as they come,” Swift told Vogue. “I’m in a magical relationship right now. And of course I want it to be ours, and low-key this is the one thing that’s been mine about my personal life.”
They broke up a year in 2016. Following rumors, Harris said in a post on social media, “The only truth here is that a relationship came to an end (and) what remains is a huge amount of love and respect.”
Tom Hiddleston (2016)
In June 2016, photos of Swift kissing Marvel star Tom Hiddleston on a beach near her Swift’s Westerly, Rhode Island practically broke the internet. A month later, Hiddleston showed up at her annual 4th of July party wearing a tank top that read, “I (heart) T.S” in red lettering.
Hiddleston confirmed the whirlwind relationship in July, telling the Hollywood Reporter that it was not, in fact, a publicity stunt.
“Well, um. How best to put this? The truth is that Taylor Swift and I are together and we’re very happy. Thanks for asking,” he said. “That’s the truth. It’s not a publicity stunt.”
Joe Alwyn (2016 – )
Swift’s current romantic partner is the actor Joe Alwyn. While the couple has been dating since 2016, they keep their relationship private — mostly.
In an interview with GQ, Alwyn shared details about the time the couple spent together during lockdown, including their experience writing music together.
Swift and Alwyn won a Grammy Award for six songs they co-wrote and produced during that time, which appeared on Swift’s album “Folklore.” He wrote under the pseudonym William Bowery.
“It was really the most accidental thing to happen in lockdown. It wasn’t like, ‘It’s 3 o’clock, it’s time to write a song!’ It was just messing around on a piano and singing badly and being overheard and then thinking, you know, what if we tried to get to the end of it together?” Alwyn said.
As for what’s next in the couple’s relationship? Alwyn says it’s not our business.
When asked his thoughts about engagement by The Wall Street Journal, Alwyn said, “If I had a pound for every time I think I’ve been told I’ve been engaged, then I’d have a lot of pound coins,” he says. “I mean, the truth is, if the answer was yes, I wouldn’t say, and if the answer was no, I wouldn’t say.”
For now, know they’re doing well: In 2022, Alwyn said is he “obviously happy” in his relationship.