Taylor Swift is the undisputed master of the heartbreak anthem. Fans of the “I Knew You Were Trouble” singer often spend time deciphering her lyrics to determine which ex-boyfriend was the inspiration for a given song.
Her former boyfriends have been back in the news with the re-recording and re-release of her previous albums like “Fearless” and “Red”. See who Taylor Swift has dated in the past.
Joe Jonas
Although Taylor and Nick Jonas’ relationship in 2008 only lasted a few months, the breakup that occurred during a 25-second phone call served as inspiration for her second album, “Fearless.”
Tracks like “Forever & Always”, “Last Kiss”, “Better Than Revenge” and “Mr. Absolutely Fine” were all written about the DNCE frontman. She later won her first Grammy for the record.
Swift performed during her opening monologue when she first hosted “Saturday Night Live” in 2009:
“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. Hey, Joe! I’m doing really well and I’m hosting ‘SNL’ but I’m not going to write about that in my monologue”.
Lucas Till
In 2009, the two co-starred in Swift’s music video for “You Belong With Me” but they first got to know each other on the set of “Hannah Montana: The Movie,” in which Swift had a brief appearance. Months later, the couple decided they were better off as friends only and ended their engagement.
Taylor Lautner
The duo also known as “Taylor Squared” met while filming “Valentine’s Day” in which they played high school sweethearts. According to rumors, Lautner was more interested in Swift than she was in him which led to their breakup. Swift apparently tried to apologize to the “Twilight” actor in her song “Back to December” about their relationship.
Cory Monteith
Swift and the late “Glee” star only dated for about a month, but she still wrote him a touching song about her feelings for him. Monteith is the subject of the song “Mine” which is about a sweet boy she barely knows.
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John Mayer
After working together on “Half of My Heart” the two went on a brief relationship that lasted only a few months. In a song named “Dear John” Swift then 20 years old lashed out at the “Gravity” singer.
Swift sang, “Dear John, I see it all now, it was terrible / don’t you think 19 is too young to be played by your dark twisted games.” Mayer commented on the song, “I will say as a songwriter that I think it’s sort of cheap songwriting.”
Jake Gyllenhaal
Even though they barely dated for three months in 2010, Swift had a lot to say about the actor in her recently re-released album “Red” which includes a caustic 10-minute version of “All Too Well” a song about the couple’s split.
The songs “We Are Never Getting Back Together”, “State of Grace” and “The Moment I Knew” are reported to have been influenced by him as well. Swift was taken aback when Gyllenhaal abruptly ended their relationship via text message, citing their age difference as the reason.
Conor Kennedy
Swift dated Robert F. Kennedy’s grandson Conor Kennedy in 2012. Given that Kennedy was only 18 and Swift was 22, the unusual pairing did raise some questions.
Even before she met Conor, Swift was a huge fan of the Kennedys. She even penned a song, “Starlight” on Bobby Kennedy and his wife Ethel’s courtship.
Harry Styles
The “Haylor” couple made their first public appearance together in December of 2015 when they were seen taking a stroll through Central Park. “Swifties” and “Directioners” at the time went crazy over the new romance, but it only lasted three months before the couple split up.
Taylor sang “We Are Never Getting Back Again” with an English accent at the Grammys the same year which appeared to be a jab at Styles who was in the audience.
Calvin Harris
After being seen shopping at Whole Foods in March 2015 wearing matching clothing, the Scottish DJ and Singer fuelled relationship speculations. They then made it public by attending the Billboard Music Awards together in May, where they engaged in some PDA for the cameras.
The couple dated for over a year, but in March 2016, Harris ended things in what her friends are calling a “brutal” separation.
You may read about other celebrities’ dating lives in our previous posts by clicking on the links below:
- Jordin Sparks Dating History: Who She is Dating Now?
- Kylie Kristen Jenner Dating History: Is She in Relationship With Anyone Now?
Tom Hiddleston
Tom Hiddleston and Taylor Swift danced together at the 2016 Met Gala. A month later, photos of them kἰssἰng on a Rhode Island beach appeared confirming their relationship. Everyone including Swift was taken aback by the “Hiddleswift” coupling.
The song “Getaway Vehicle” is said to have been inspired by her regret at starting a new relationship so soon after her breakup with Harris. Nonetheless, the pair split up a short time later.
Joe Alwyn
In 2016, Swift was in her longest and most private relationship to date. She began dating actor Joe Alwyn after meeting him at the 2016 Met Gala though their relationship was not publicly known until the following year. In her upcoming documentary on her life, “Miss Americana” she says:
“I was falling in love with someone who had a very normal, balanced existence. We both agreed that we wanted our relationship to be private. I felt good. Yet I wasn’t happy in the ways I’d been taught to be happy. It was joy without interference from anyone else. We were just pleased”.
After more than six years together, the couple broke up in April of 2023.
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