Taylor Swift’s dating history: Famous Boyfriends and their Songs

Taylor Swift has a knack for turning a painful breakup into a smash hit. It’s something she never hides, joking that if she and a guy break up, she’ll likely use their relationship as inspiration for a song – or, if they’re lucky, an album. With the re-release of Swift’s fourth album, Red (Taylor’s Version), and renewed interest in her brief relationship with Jake Gyllenhaal, we thought it was time to look back at her other notable romances.

Joe Jonas (Last Kiss and Forever and Always)

Taylor Swift’s first public relationship was with Joe Jonas of the Jonas Brothers. Jonas abruptly ended their relationship over the phone after three months of dating (25 seconds, to be exact).

We give credit to the breakup for providing great musical fodder. Swift’s songs Last Kiss, Forever, and Always are said to have been inspired by her breakup with Jonas.

Lucas Till (You Belong with Me)

After playing the next-door neighbor and love interest in Swift’s You Belong With Me music video, Hollywood heartthrob Lucas Till and Swift dated for a hot minute.

While Swift never admitted they dated, Till told MTV that they did for a short time. They never got along because he only wanted her as a friend.

Taylor Lautner ( Back to December)

Taylor Swift and Taylor Lautner dated in real life after meeting on the set of the 2010 romantic comedy Valentine’s Day. Back to December is said to have been written by the singer for Lautner. When asked what he thought of the song, Lautner replied, “That’s what she does.” Things never went well for them, but they are doing well with their professional investments.

John Mayer ( Dear John)

John Mayer and Taylor Swift dated for a short time after collaborating on his song Half of My Heart, but things quickly soured. Following their breakup, Swift wrote a song called Dear John (which didn’t hide who it was about), and Mayer was not pleased.

Cory Monteith (Mine)

Taylor Swift and Cory Monteith, an actor, began dating in the spring of 2010. Swift’s song Mine was released following their rumored split. The media has made a connection between Swift’s relationship rumors and Monteith’s comments on the song. Another argument is that they began dating in the same year that the credit was released.

Jake Gyllenhaal (All too Well)

Taylor Swift dated Jake Gyllenhaal, which sparked outrage on the internet.

Swift, then 20, was in a brief but widely publicized relationship with Gyllenhaal. The couple was frequently photographed walking hand-in-hand in New York City and Los Angeles, and paparazzi photographs of them have become somewhat iconic. The relationship ended after a few months, with Gyllenhaal reportedly calling it quits due to their age difference. She did, however, publish All Too Well: The Short Film.

Conor Kennedy (Begin Again)

During 2012, Swift dated Conor Kennedy, the grandson of former US Attorney General Robert F. Kennedy. They had a whirlwind romance worthy of a love song, which she appears to have recorded in her hit Begin Again.

Harry Styles (I Knew You Were Trouble )

Another well-publicized love story. Despite only dating for a month, the couple exchanged paper airplane necklaces, went on a tour of New York City, and even had a snowmobile accident. She wrote I Knew You Were Trouble, and her album 1989 is littered with subtle nods to Styles. Their December romance is best described by the song “Out Of The Woods.”

Calvin Harris (This is What you Came for)

Swift met DJ Calvin Harris at the Elle Style Awards in February 2015, and by March, they were inseparable. Despite working together on music investments, the couple split up. Harris, according to multiple sources, was the one who put an end to it.

Tom Hiddleston (Getaway Car)

Swift kissed British actor Tom Hiddleston on a beach in Rhode Island shortly after Harris and Swift ended their relationship.

The couple traveled around the world together, stopping in Italy, America, Australia, and England before calling it quits after only three months. According to rumors, Hiddleston wanted the relationship to be more public.