Singer-songwriter Taylor Swift has a song for almost any mood. “Love Story” for the days when you finally find yourself falling for someone, “Shake It Off” for when someone takes a dig at you and you need to take a step back, and “Cruel Summer," the perfect summer bop for those windows-down-driving-along-the-beach kind of day.
Aside from all of her upbeat, happy jams, Swift’s songs have become associated with something else: heartbreak. Remember the whole Jake Gyllenhaal “All Too Well” scarf drama? (I wonder if he ever gave it back?) From Joe Jonas to Harry Styles to her recent ex-boyfriend Joe Alwyn, Swift has had multiple partners over the years, some long-lasting and others fizzling out fast.
Joe Jonas
He was hot and then he was cold. Swift and the Jonas Brothers frontman began dating in 2008. But after three short months, Jonas dumped Swift, who was 18 at the time, over the phone. The whole phone call? Lasted 25 seconds. While a phone call isn’t the most chivalrous way to end a relationship, fans think the two are on good terms today. Back in 2020 when Swift released, “Invisible String,” fans raised their eyebrows at one specific line—“Cold was the steel of my axe to grind/ For the boys who broke my heart/ Now I send their babies presents.” Coincidentally, around the same time the song was released, Jonas and wife Sophie Turner were preparing for their first child together.
Taylor Lautner
Swift and The Twilight werewolf dated for around three months in 2009, and starred alongside each other as lovers in the 2010 film Valentine’s Day. While the relationship was short-lived, something about their relationship has had a lasting impact. In 2016, Lautner revealed during a livestream that Swift’s hit, “Back to December” was actually about him.
Lucas Till
Lucas Till and Swift dated briefly in 2009 after they both appeared in Hannah Montana: The Movie. Till, with a major role, played Miley Cyrus's love interest, while Swift made a cameo and performed "Crazier," in the film. The two quickly broke up, and, according to Till, in an MTV interview, "I really just liked her as a friend. That’s the only reason that didn't work out."
John Mayer
The two musicians briefly dated toward the end of 2009 and into the beginning of 2010. However, their age gap caused quite a controversy. Swift was only 19 at the time, while Mayer was 32.
Some point after their split, Swift released “Dear John,” which seemed to directly reference her and Mayer’s relationship. The lyrics read: “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?” Mayer addressed the song in a 2012 interview with Rolling Stone. “It was a really lousy thing for her to do,” he said. He also went on to say that it was “cheap songwriting.” (We disagree.)
Cory Monteith
Swift and Glee actor were briefly linked in 2010. While it was never confirmed if the two were dating, Monteith is reportedly the inspiraton behind Swift's song "Mine."
Conor Kennedy
In 2012, Swift was briefly linked with Conor Kennedy—yes, a member of the Kennedy family. Swift, 22, and Kennedy, 18, were first spotted together in July. From sweet pictures of them kissing to pictures of the two visiting Kennedy's mother's grave, the two were spotted multiple times together for the next couple of months. But by the end of October, the pair was no more.
Harry Styles
Swifties and Harries are still talking about this one, often referencing the two as their "divorced parents." In the iconic autum stroll photo above, the two were photographed together for the first time in December 2012 walking through Central Park. The two began dating before the photo began circulating, but the exact time is unknown. By January, the two "Daylight" singers—yes, they both have songs called "Daylight"— had reportedly called it quits.
Calvin Harris
Even though Harris did not meet Swift in the summer, their relationship lasted for a little over a year. The two first met at the Elle Style Awards in 2015 (there's even a photo of the moment they met) and quickly hit it off. After around 15 months of dating, the two ended things in July 2016, and things got ugly when Harris went on a rant on Twitter.
Tom Hiddleston
In June 2016, just two weeks after her split from Harris, Swift was spotted kissing Tom Hiddleston. But after four short months, the two had parted ways. It's also speculated that Swift's "Getaway Car" was inspired by Hiddleston helping her end her relationship with Harris.
Joe Alwyn
Swift and actor Joe Alwyn had been linked since 2016. The two were notoriously private about their relationship and rarely made comments about the relationship. When engagement rumors in 2022 began swirling, Alwyn told the Wall Street Journal Magazine, “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." Well, did he spill? Nope. He continued, “I mean, the truth is, if the answer was yes, I wouldn’t say, and if the answer was no, I wouldn’t say."
However, in April 2023, fans were shocked to learn that the pair had broken up after over 6 years together. According to Entertainment Tonight, a source explained, "it was not dramatic," and that, "the relationship had just run its course. It's why [Alwyn] hasn't been spotted at any shows."
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