Taylor Swift's dating history: How her past relationships wind up in songs (2024)

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.

One of the most famous examples is “Style” from “1989,” which fans have long speculated to be about Harry Styles. Swift notably dated the former One Direction star between 2012 and 2013, which predates the release of her fifth studio album in October 2014.

Swifties were able to read between the lines yet again when Swift re-released “1989” in October 2023 and its five new vault tracks. One of them, titled “Is It Over Now?”, includes real-life references to her time with Styles.

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 her songs are about — but fans have turned guessing into a pastime. 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. And maybe fans have a love song about football pro Travis Kelce on the way.

Read on for a brief refresh of Swift’s dating history broken down by album “era” — and the songs her exes may have inspired.

"Fearless" era

Joe Jonas (2008)

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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 DeGeneres that when the couple started to go downhill, she booked a last-minute studio session to record the song “Forever & Always.”

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)

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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 because 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.

"Speak Now"

Taylor Lautner (2009)

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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)

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John Mayer and Swift met after collaboratingon 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 Stone 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 was19 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 19's 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.”

"Red" era

Jake Gyllenhaal (2010)

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Jake Gyllenhaal and Swift dated briefly in 2010. Since then, people have speculated whether Swift wrote the song “All Too Well” about their relationship.

When Swift released a 10-minute remake of “All Too Well” in 2021, fans close-read lyrics for more proof of the 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, where Swift sings that she left her scarf — Swift has never confirmed that she wrote the song about him. For her part, Maggie Gyllenhaal said on “Watch What Happens Live” in 2017 that she was “in the dark about the scarf.”

Conor Kennedy (2012)

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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 WSJ. “So I just kind of wrote that song from that place, not really knowing how they met or anything like that.”

"1989" era

Harry Styles (2012 - 2013)

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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 in New York City.

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” are among songs about him.

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)

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Swift and DJ Calvin Harris went public with their relationship at the2015 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 toldVogue. “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.”

"Reputation" era

Tom Hiddleston (2016)

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In June 2016, photos of Swift kissing Marvel star Tom Hiddleston on a beach near her home in Westerly, Rhode Island, practically broke the internet. A month later, Hiddleston showed up at her annual Fourth 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.”

They broke up later that summer.

"Reputation," "Lover," "Folklore," "Evermore" and "Midnights" eras

Joe Alwyn(2016 - 2023)

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Swift and British actor Joe Alwyn dated from 2016 to 2023. News of their breakup reverberated among her fandom.

In a 2022 interview with GQ, Alwyn shared details about the time the couple spent together during COVID-19 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.

Swift confirmed that some lyrics from her 10th studio album, “Midnights,” were about her relationship at the time. The first track, “Lavender Haze,” put a spotlight on her feelings towards dating in the public life.

“I think a lot of people have to deal with this now, not just like ‘public figures,’ because we live in the era of social media,” she began. “And if the world finds out that you’re in love with somebody, they’re going to weigh in on it.”

“My relationship for six years, we’ve had to dodge weird rumors, tabloid stuff — and we just ignore it,” she said. “This song is sort of about the act of ignoring that stuff to protect the real stuff.”

Alwyn rarely spoke about his relationship with Swift. Engaged rumors had swirled, and Alwyn briefly addressed them in conversation with the The Wall Street Journal in 2022.

“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 said. “I mean, the truth is, if the answer was yes, I wouldn’t say, and if the answer was no, I wouldn’t say.”

After news of their breakup in 2023, Swift released a surprise vault track from the writing of “Midnights” titled “You’re Losing Me.” Fans speculated that the song addressed her split with Alwyn, with heartbreaking lyrics like, "I wouldn’t marry me either/ A pathological people pleaser/ Who only wanted you to see her."

Matty Healy (2023)

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After Swift and Alwyn’s breakup, rumors circulated that the pop singer was taking her friendship with Matty Healy, lead singer of The 1975, to the next level.

Headlines about their rumored romance spread in May, and the pair were photographed holding hands in New York City shortly after. Fans also pointed to footage of Swift and Healy mouthing a similar romantic message at separate concerts within a few days of each other.

The pair first became linked in 2014 —initially sparking dating rumors —when they were separately photographed wearing each other’s merch. Healy sported a shirt with the “1989” album cover while Swift wore a 1975 tee.

Their rumored romance sparked backlash after Swift collaborated with rapper Ice Spice for a remix of her song “Karma.” Healy had previously made comments about Ice Spice that were deemed racist, and some argued her collaboration with the rapper was calculated.

Others wanted her to address Healy’s problematic comments due to their apparent connection.

By Fourth of July, Swift was seemingly single and spent the holiday with longtime friends Selena Gomez and the Haim sisters.

The official Instagram for Haim re-shared the photos with the caption “single summer.”

Travis Kelce (2023-2024)

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In July of 2023, Kansas City Chiefs player Travis Kelce attended Swift’s “Eras Tour” and later revealed that he planned to make a move on the superstar. On his podcast “New Heights,” Kelce said he tried to give Swift a friendship bracelet, a staple accessory for attending one of her concerts, with his phone number on it —but failed.

Swift got wind of Kelce’s attempt to woo her — and since then, a romance between one of the biggest pop stars and a beloved pro athlete has unfolded before the world’s eyes.

Swift first appeared at a Chiefs game to cheer on Kelce in late September, and was spotted at various games through the whole season, culminating in an incredible Super Bowl win for the Chiefs in Las Vegas. Kelce, meanwhile, used his downtime to travel to various international stops on Swift’s “Eras Tour,” including Australia and Singapore.

One of their earliest public appearances together was in New York City in October, during a date night where they held hands and even visited “Saturday Night Live.”

In the months since, fans have marveled at the “invisible strings” that had been connecting Swift and Kelce all along. The theories are inspired by Swift’s 2020 song “Invisible String,” which speaks to the ways people’s paths connect before they start dating. Swift and Kelce’s invisible strings include shared birth year and arrow pose, the colors red and gold and the word “arrowhead.”

Jordan Greene

Jordan Greene is an editorial intern at TODAY.com. She is currently studying magazine journalism, political science and religion at Syracuse University. Previously, she interned at the Forward, Punch Magazine in the San Francisco Bay Area and Minute Media. She loves adventuring to new places and watching the sunset at the beach. Follow her on Twitter here.

Taylor Swift's dating history: How her past relationships wind up in songs (2024)


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