Taylor Swift's Dating and Relationship History—and the Songs Each Lucky Guy Inspired

Jessica Sager

April 26, 2024 at 10:52 PM·20 min read

Taylor Swift

Taylor Swift's dating history has been the subject of a whole lot of gossip and a whole lot of tunes since she first name-dropped a guy named Drew in "Teardrops on My Guitar"—and her latest romance is sure to inspire some more pop canon and self-mythologizing love stories in song.

Swift's muses have run the gamut from classmates who turned out to be world-class jerks, musicians who are less famous than she is, a lot of Brits and one athlete. Look back at the "Blank Space" singer's "long list of ex-lovers" through the years—and whose name she's writing now.

Taylor Swift's Dating History

Andrew "Drew" Hardwick

Andrew "Drew" Hardwick was the subject of Swift's breakout ballad "Teardrops on My Guitar." Swift penned the song about Hardwick, a high-school classmate, after he reportedly ignored her. Swift later recalled recalled to The Washington Post that he showed up in her driveway two years after the song became a hit.

"He was like: 'Hey, how’s it going?' And I'm like: 'Wow, you're late? Good to see you?'"

From the sounds of it, Swift dodged a bullet with Hardwick, who was arrested for alleged child abuse in 2015.

Related: Taylor Swift Dictionary

Sam Armstrong

Sam Armstrong dated Swift in high school and is rumored to be the inspiration for her songs "Picture to Burn" and "Should've Said No."

Stephen Barker Liles

Swift wrote "Hey Stephen" about Stephen Barker Liles of the band Love and Theft. She had a crush on him when they toured together in 2008, but they never dated.

Joe Jonas

Swift dated Joe Jonas for several months in 2008—the Jonas Brothers' peak—until he dumped her in a 27-second phone call. She went on to write several songs about their relationship, including "Hello Mr. Perfectly Fine (Taylor's Version) (From the Vault)" and "Forever and Always," as well as "Better Than Revenge," which slut-shamed Camilla Belle, who Jonas dated post-Swift. (Swift updated the lyrics for her "Taylor's Version" of the song to remove the Belle-slamming.) He is also believed to have inspired "Holy Ground" from Red, a song that looks back on their romance fondly from a position of friendship and with the wisdom that comes with age and growing up.

Swift was friendly with Jonas in recent years, most notably when he dated her Squad member Gigi Hadid. However, following his messy divorce filing from Sophie Turner, Swift has made it clear that she's Team Sansa.

Martin Johnson

Neither Swift nor he have confirmed it, but she was rumored to have briefly dated Boys Like Girls frontman Martin Johnson when they co-wrote a song for The Hannah Montana Movie together and collaborated on the band's track "Two Is Better Than One" and her song "If This Was a Movie."

According to Inside Edition, Swift's team—and her parents—didn't think the pop-punk star was good for her image and forced her to end the fledgling relationship.

Their romance is rumored to have inspired her crossover smash "Love Story," so really, all's well that ends well.

Adam Young

Swift met Owl City singer Adam Young in what he recalled was either 2009 or 2010, and they each developed a mutual crush. She wrote "Enchanted" about him, and he covered the song for Valentine's Day in 2013 in tribute to her. Aw!

Taylor Lautner

Swift co-starred with Taylor Lautner in the movie Valentine's Day (playing a couple, of course!) and even shouted him out (and slammed Jonas!) during her musical Saturday Night Live monologue in 2009, but the romance was short-lived. He inspired her songs "Today Was a Fairytale" (see his dark gray T-shirt in the photo above, which she mentions in the track) and "Back to December," which was a song about their split. They're so friendly to this day that he starred in her music video for "I Can See You" in July 2023—and his wife, also named Taylor, is a Swiftie, too.

Cory Monteith

Swift was rumored to briefly date Glee star Cory Monteith, and some Swifties believe that her hit song "Mine" was about him. Monteith died from an accidental overdose in 2013. At the time, Swift tweeted, "Speechless. And for the worst reason."

John Mayer

Swift had a dalliance with John Mayer in 2009, and she's featured on his hit "Half of My Heart." When they dated, she was 19 to his 32.

While it's unclear exactly what the sketchy nature of their relationship was, it's clear that it ended very badly: Swift wrote "Dear John" clearly about Mayer, though she would neither confirm or deny it, and it's speculated that her vault tracks "Could've, Would've, Should've" and "Foolish One" are also about the Battle Studies singer.

Mayer later told Rolling Stone of "Dear John," "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." He added, "I never got an email. I never got a phone call. I was really caught off guard. [That's] abusing your talent to rub your hands together and go, 'Wait 'til he gets a load of this!' That's bulls—t."

Swift's song "The Manuscript" from The Tortured Poets Department is suspected to be about Mayer or Jake Gyllenhaal—or perhaps an amalgam of them both—as it looks back on a relationship with a 30-something when she was too young and naive to navigate those waters.

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Jake Gyllenhaal

Jake Gyllenhaal inspired most of Red, including the title track, the criminally underrated "State of Grace," "We Are Never Ever Getting Back Together," "I Bet You Think About Me," "The Moment I Knew" and fan-favorite "All Too Well"—as well as "All Too Well (10 Minute Version)." The pair spent Thanksgiving together with Gyllenhaal's family in 2010 and were on-again-off-again through some of 2011 as well. He was 29 and she was 20 when they began seeing each other.

Basically any and everything else you've ever wanted to know about their relationship is told very literally in Swift's All Too Well: The Short Film, including Gyllenhaal (played by Dylan O'Brien) allegedly no-showing to Swift's 21st birthday party, with Swift portrayed by Sadie Sink, as well as dismissing and gaslighting her.

(She also spelled out "maple lattes" in the lyrics of "All Too Well" in the liner notes of the original Red, a beverage they reportedly enjoyed together.)

Gyllenhaal is also expected to be at least part of the subject of her song "The Manuscript," which is about a short-lived relationship with an older guy who treated her badly. Further supporting that theory? In her All Too Well: The Short Film, Swift's character is an author.

Conor Kennedy

Hey, remember when Swift was 22 and dating a literal high-school kid? Because Pepperidge Farm remembers.

Swift and Conor Kennedy were first spotted together in early July 2012 when Kennedy was still 17 (he turned 18 on July 24, 2012). They enjoyed a whirlwind romance, during which Swift reportedly crashed a Kennedy wedding with her beau. Swift also purchased a home not far from the Kennedy compound in Hyannis Port, Mass., but that was for riches, not romance—Vanity Fair reported that she resold the property for a $1 million after their summer fling ended that September.

Swift had no bad blood with Kennedy post-breakup, and her Red song "Begin Again" is believed to be about him—and "Starlight" is about his grandmother, Ethel Kennedy. He may also have been one of the romances she references in "The Manuscript," in which she describes dating "boys who were her own age" after poor experiences with older men. Again, Conor wasn't actually her age and was underage when they first were seen hanging out, but the age gap was still smaller than hers with Gyllenhaal or Mayer.

Harry Styles

After her amicable breakup from Kennedy, Swift went public with Harry Styles, then still a member of One Direction. Swift was on the cusp of her 23rd birthday, while Styles was 18.

The pair were rumored to have first met in March 2012, with a mutual crush brewing at the time, but nothing concrete happening until later. Their relationship reportedly gained speed after her split from Kennedy in fall 2012, and in early that December, they were famously photographed together in Central Park.

"When I see photos from that day [in Central Park], I think: Relationships are hard, at any age. 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 recalled to Rolling Stone in 2017. "I just wanted it to be a normal date."

They rang in Swift's 23rd birthday and the holidays together that December. There was a snowmobile accident and a love of hot-and-cold, on-again-off-again drama, but by January, the romance was over, with photos of Swift, clad in a blue dress, solo on a boat that will live on in infamy.

That blue dress would later be referenced in her music video for "Out of the Woods," which she later said was inspired by the anxiety of a rocky relationship (and in which she drops a "paper airplane" reference, likely about the necklace he gave her).

"It felt very fragile, it felt very tentative," she said. "And it always felt like, 'Okay, what's the next roadblock? What's the next thing that's gonna deter this? How long do we have before this turns into just an awful mess and we break up? Is it a month? Is it three days?'"

In addition to "Out of the Woods," Styles is rumored to have inspired her songs "Style" (obviously), "This Love," "Clean," "I Wish You Would," "How You Get the Girl," "I Know Places," "All You Had to Do Was Stay," "I Knew You Were Trouble," "Question...?" and possibly "Maroon." He's also likely one of the younger guys (who, again, she lyrically insists were her own age") that she references in "The Manuscript." What a muse!

The pair are on friendly terms now, as evidenced by their enthused reactions to one another at the 2023 Grammys.

Taylor Swift and Harry Styles chatting at the 2023 #GRAMMYs via @Variety pic.twitter.com/B2vB1kMmZo
— Taylor Swift Updates (@SwiftNYC) February 6, 2023

Calvin Harris

In February 2015, Swift and DJ Calvin Harris began dating.

They reportedly met that February after mutual friend Ellie Goulding introduced them. Goulding later told The Sun (via The Mirror), "Calvin is a really great mate, and he's so fantastic, and Taylor is such a cool person who I love. I thought, 'They're both really awesome and both really tall, they'll be brilliant together.'"

They went Instagram official that April (though all posts have sadly since been deleted) and made their first public appearance together at the May 2015 Billboard Music Awards.

The couple celebrated their anniversary in March 2016 with a tropical vacation.

In April 2016, Swift thanked Harris in her speech at the iHeartRadio Music Awards, telling the crowd, "You know, for the first time, I had the most amazing person to come home to when the spotlight went out and when the crowds were all gone. So I want to thank my boyfriend, Adam, for that." (Harris' real name is Adam Wiles!)

That same month, 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."

By June 2016, however, the couple called it quits, and it got messy. After their breakup, it was revealed that Swift co-wrote his hit "This Is What You Came For" under the pseudonym Nils Sjoberg, which they reportedly agreed upon in advance to minimize fan and media frenzies over their relationship and keep the focus on the song. When the track was released on April 29, 2016, Harris said in an interview that he and Swift never discussed working together and that he didn't see it happening—which sources close to Swift later said she found disrespectful.

“Hurtful to me at this point that [Taylor] and her team would go so far out of their way to try and make ME look bad at this stage," Harris wrote of the move in a series of since-deleted tweets. "I know you’re off tour and you need someone new to try and bury like Katy [Perry] ETC but I’m not that guy, sorry. I won’t allow it."

The song dropped just before the 2016 Met Gala, where Swift danced with the man who'd be the next entry in her self-described "long list of ex-lovers."

Harris is believed to have inspired her songs "The 1" and "I Forgot That You Existed."

Tom Hiddleston

Swift famously danced with Loki star Tom Hiddleston at the 2016 Met Gala, which she co-chaired.

She was still in a relationship with Harris at the time, and sources told TMZ that Harris suspected something was up for weeks before Harris and Swift announced their split.

Less than two weeks after Swift and Harris' breakup was announced, Swift and Hiddleston were photographed kissing on the rocks near her Rhode Island mansion. The pair embarked on a globe-trotting romance, visiting the Vatican, dining in Nashville, going to Australia and even hanging out with Hiddleston's mom in the U.K. Hiddleston was infamously photographed wearing a tank top emblazoned with "I Heart T.S." at her 4th of July party.

"Everything you do you have to make sure you truly believe in it and as long as you know that, it doesn't matter what anyone else says about it," Hiddleston told PEOPLE in July 2016. "Because the nature of being a public figure is that everyone will have an opinion about anything you do, and as long as you know why you've done something and you've committed to it with authenticity then you're OK."

By September 2016, however, the summer fling was over.

Hiddleston is rumored to have inspired her songs "Getaway Car" and "Dancing With Our Hands Tied" from Reputation.

John Alwyn

Taylor Swift and Joe Alwyn in January 2020<p>Christopher Polk/NBC/NBCU Photo Bank</p> — Taylor Swift and Joe Alwyn in January 2020
Christopher Polk/NBC/NBCU Photo Bank

As it turns out, the 2016 Met Gala was a busy night for Swift.

In addition to meeting Hiddleston at fashion's biggest night, it's rumored that's when she also met British actor Joe Alwyn, based on the lyrics to her song "Dress" from Reputation: "Flashback to when you met me / Your buzz cut / And my hair bleached." Of course, that's exactly how each of their hair was at the Met Gala.

The relationship was first reported in May 2017, with sources telling The Sun that the couple had been dating for several months at the time. They went Instagram official in May 2018, but never posed together on red carpets or discussed their relationship at length while they were together.

"I've learned that if I do [talk about Alwyn], people think it's up for discussion, and our relationship isn't up for discussion," Swift told The Guardian in 2019. "If you and I were having a glass of wine right now, we'd be talking about it—but it's just that it goes out into the world. That's where the boundary is, and that's where my life has become manageable. I really want to keep it feeling manageable."

In January 2020, Alwyn was spotted in scenes of Swift's Netflix documentary, Miss Americana, and that year, they collaborated on songs from her albums folklore and evermore, with Alwyn using the pseudonym "William Bowery."

The couple appeared to be rock solid to the point that it was rumored they were engaged—so it came as a huge shock when their split was announced in early April 2023; the couple is rumored to have broken up sometime in March 2023 based on Swift's Eras tour setlist changes around that time.

"They've had rough patches before and always worked things out, so friends thought they would take some time apart but eventually come back together," a source told PEOPLE at the time, adding, "Joe has struggled with Taylor's level of fame and the attention from the public."

In The Tortured Poets Department, Swift hints at boredom and feeling stifled and suffocated in her relationship with Alwyn, as well as at having an emotional affair at least towards the end of it, but still being sad about losing him.

Alwyn is rumored to have inspired a slew of Swift's songs, including:

"Endgame"
"...Ready For It?"
"Delicate"
"Gorgeous"
"King of My Heart"
"Dress"
"Call It What You Want"
"New Year's Day"
"Lover"
"Cruel Summer"
"I Think He Knows"
"Paper Rings"
"London Boy"
"Cornelia Street"
"Daylight"
"Peace"
"Invisible String"
"The Lakes"
"Long Story Short"
"Lavender Haze"
"Snow on the Beach"
"Labyrinth"
"Sweet Nothing"
"Mastermind"
"All of the Girls You Loved Before"
"You're Losing Me"
"Fresh Out the Slammer"
"Guilty as Sin?"
"So Long, London"
"How Did It End?"
"The Black Dog"
"The Albatross"

Matty Healy

Shortly after her split from Alwyn, Swift was linked with Matty Healy, edgelord extraordinaire and frontman of The 1975. The pair had what Healy later called a "flirtation" in late 2014 through early 2015. You can see her at a 1975 show here:

In September 2022, it was rumored that The 1975 would be featured on Midnights. Healy confirmed in November 2022 that they did work together on some material, but none of it made the final cut for the album.

Fast forward to January 2023: Swift made a guest appearance at The 1975's concert in London. By that May, Healy and Swift were dating. He was spotted at Swift's Eras tour shows, leaving a recording studio with her and holding hands at a private New York City eatery.

Swift came under fire for dating Healy, who spoke about watching Black women be "brutalized" in pornography and for laughing at racist jokes about Ice Spice on a podcast. Incidentally, in early June, Swift and Healy split—and just days before that was announced, she dropped a music video and remix for her song "Karma" featuring none other than Ice Spice.

Some speculate that "Question...?" isn't about Styles, but is actually about Healy.

Most of Swift's The Tortured Poets Department is about Healy, including:

"Fortnight"
"The Tortured Poets Department," which specifically references Healy's love of typewriters
"My Boy Only Breaks His Favorite Toys"
"Down Bad"
"But Daddy, I Love Him"
"Fresh Out the Slammer"
"Guilty as Sin?"
"I Can Fix Him (No Really I Can)"
"loml"
"I Can Do It With a Broken Heart"
"The Smallest Man Who Ever Lived"
"The Alchemy" (also partly about Travis Kelce)
"imgonnagetyouback"
"Chloe or Sam or Sophia or Marcus"
"I Look In People's Windows"
"The Prophecy"
"Peter"

After The Tortured Poets Department was released, it was speculated that songs previously believed to be about Alwyn or others were actually about Healy, including:

"The 1" from Lover
"Cardigan" from folklore, which mentions "Peter losing Wendy" (and which she sang to him live in the early dates of her Eras Tour)
"Happiness" from evermore, which shares a title with a 1975 song
"Labyrinth" from Midnights, which may be referenced in the "hedge maze" lyric from "Guilty as Sin?"
"Question...?" from Midnights, which may be about reconnecting with Healy in 2015 at the Brit Awards, which Harris also attended (and perhaps also referencing the 2020 NME Awards, where they also hugged and chatted)
"Paris" from Midnights, which shares a title with a 1975 song

Travis Kelce

Taking a break from Brits, Swift is currently linked to Kansas City Chiefs tight end Travis Kelce in what may be the most publicized relationship of her life so far.

In July 2023, Kelce said he was bummed he didn't get to give Swift his number on a friendship bracelet at the Kansas City stop of her Eras tour.

No matter: She attended the Chiefs game on Sept. 24, 2023, hanging out with Kelce's mom in a friends and family suite.

Travis Kelce and Taylor Swift spotted together after the Chiefs' big win ??

(via @paytonsun) pic.twitter.com/nwKtfdr0vU
— ESPN (@espn) September 25, 2023

Following the game, Swift and Kelce left together.

Travis Kelce driving Taylor Swift and leaving the Arrowhead stadium together ??? pic.twitter.com/yuNhD3xz0G
— Taylor Swift Updates (@SwiftNYC) September 25, 2023

PEOPLE reported that the pair had been hanging out for several weeks and getting to know one another before and since the big game—and that Kelce rented out a restaurant after his team's victory so he and Swift could dine privately with his family and friends. Privately. We know about it, and Kelce, his teammates, his brother and NFL commentators keep talking about it, but remember, it's all very private.

By November 2023, Kelce had met Swift's dad and she'd hung out with both of his parents and visited her on tour in Argentina, where she called him out during a performance of her song "Karma," changing the lyric "Karma is the guy on the screen / Coming straight home to me" to "Karma is the guy on the Chiefs / Coming straight home to me."

The same month, Kelce told The Wall Street Journal magazine that mutual friends helped play matchmaker for the pair after he was initially unable to meet her at her Kansas City Eras tour.

"There were definitely people she knew that knew who I was, in her corner [who said]: 'Yo! Did you know he was coming?' I had somebody playing Cupid," he recalled. "[Swift] told me exactly what was going on and how I got lucky enough to get her to reach out."

"When I met her in New York, we had already kind of been talking, so I knew we could have a nice dinner and, like, a conversation, and what goes from there will go from there," he continued.

Swift wrote several songs about her romance with Kelce on The Tortured Poets Department, including "The Alchemy" (complete with heavy-handed lyrics including "So when I touch down / Call the amateurs and cut 'em from the team / Ditch the clowns, get the crown / Baby I'm the one to beat") and "So High School."

Taylor Swift’s list of boyfriends

Andrew "Drew" Hardwick
Sam Armstrong
Stephen Barker Liles
Joe Jonas
Martin Johnson
Adam Young
Taylor Lautner
Cory Monteith
John Mayer
Jake Gyllenhaal
Conor Kennedy
Harry Styles
Calvin Harris
Tom Hiddleston
Joe Alwyn
Matty Healy
Travis Kelce

Next, Find Out How Much Money Taylor Swift Has Made By Capitalizing On Her Highly Publicized Love Life

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