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

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.

Related: See Taylor Swift Through the Years

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.

Related: Every Taylor Swift Album, Ranked

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.

Related: A Complete Guide to Taylor Swift’s Purr-fect Companions—Her Cats!

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.

Related: The Best Taylor Swift Nicknames

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!

Related: Exactly Why Taylor Swift Is Re-Recording All of Her Old Albums

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."

Related: The Funniest Misheard Taylor Swift Lyrics

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.)