Taylor Swift's dating history: Every boyfriend before Travis Kelce and songs about them

Recently, Taylor Swift accepted a marriage proposal from American football star Travis Kelce. The couple's possible wedding is already being called the most anticipated event of the year. Against this backdrop, we suggest recalling all of the singer's boyfriends and the hits she wrote after each of them.
Joe Jonas
In 2008, the performer and Taylor were together for just a few months. The breakup, according to rumors, happened over the phone in just 25 seconds.
The singer turned this drama into music, using the experience for the album Fearless, which later earned her her first Grammy.
Taylor Swift and Joe Jonas (photo: Getty Images)
Among the songs inspired by this stage are "Forever & Always," "Last Kiss," "Better Than Revenge," and "Mr. Perfectly Fine."
Lucas Till
The actor who appeared in the video for "You Belong With Me" was also a brief love interest of the singer. They met on the set of the film Hannah Montana. Eventually, both agreed to remain friends.
Taylor Lautner
The romance between the two Taylors began on the set of the movie "Valentine's Day". Fans believe that "Back to December" is the singer's apology to the Twilight star.
"You gave me all your love and all I gave you was goodbye," Swift sings. In response, Lautner said: "That's just who she is."
Taylor Swift and Taylor Lautner (photo: Getty Images)
Cory Monteith
Glee star Cory Monteith, who recently died under mysterious circumstances, had a short-term relationship with the singer.
Taylor Swift and Cory Monteith (photo: Getty Images)
It is believed that the track "Mine" was dedicated to him.
John Mayer
Working on the song "Half of My Heart" turned into a romance. Taylor was 20, John was 32. The song "Dear John" is a direct address to Mayer.
"Don't you think 19 is too young to be played by your dark twisted games?" the lyrics say.
After its release, the musician called the song a "cheap songwriting."
Taylor Swift and John Mayer (photo: Getty Images)
Jake Gyllenhaal
In Taylor's relationship with Jake Gyllenhaal, the significant age difference—he is 10 years older—was felt. This likely affected the course of their romance.
Later, in the song "All Too Well," Taylor emotionally described the painful experiences tied to this relationship.
"They say all's well that ends well, but I'm in a new hell. Every time you double-cross my mind. You said if we had been closer in age, maybe it would've been fine. And that made me want to die," the lyrics say.
In this song, the artist also recalled other painful moments, including when her beloved didn't show up on her birthday and didn't return her red scarf that became a symbol of lost love.
Conor Kennedy
Robert Kennedy's nephew Conor, who volunteered in the war in Ukraine, dated Swift for several months in 2012.
Conor Kennedy (photo: instagram.com/jconorkennedy)
She was 22, he was 18. This romance inspired the song "Starlight."
Harry Styles
The stars appeared together in December 2015.
Taylor Swift and Harry Styles (photo: Getty Images)
Three months later, the couple broke up, and Taylor performed "We Are Never Getting Back Together" at the Grammys with a distinct British accent, seemingly addressing the track to Harry.
Calvin Harris
The DJ and the singer began appearing together in 2015, officially confirming their relationship at the Billboard Music Awards. The couple broke up a year later, and it wasn't "painless", as Harris's friends said.
Taylor Swift and Calvin Harris (photo: Getty Images)
Tom Hiddleston
At the 2016 Met Gala, the English actor and the singer just danced—a month later, paparazzi caught them kissing.
Taylor Swift and Tom Hiddleston (photo: Getty Images)
The song "Getaway Car" is believed to be inspired by these events. The romance itself didn't last long.
Joe Alwyn
In 2017, Taylor Swift began a relationship that seemed like it might finally be a long-lasting, drama-free one. But, despite fans' hopes, her romance with British actor Joe Alwyn ended in 2023.
The couple shared a passion for music and a love of cats. Joe even got involved in Swift's work, co-writing several songs on her albums Evermore and Folklore - under the pseudonym William Bowery.
Taylor Swift and Joe Alwyn (photo: Getty Images)
They spent the lockdown together with their beloved cats: Meredith, Benjamin, and Olivia.
"We decided we wanted our relationship to be private. I was happy. But I wasn't happy in the way I was trained to be. It was happiness without anyone else’s input. We were just happy," the star said about the relationship.
About Taylor Swift and Travis Kelce's engagement
Recently, Taylor shared a touching photo with fans. She poses in a luxurious green garden, richly decorated with flowers. It was in this enchanting setting that her lover, athlete Travis Kelce, proposed. The star has also already shown off her engagement ring, a piece with a massive diamond in a gold setting.
Taylor Swift and Travis Kelce (photo: instagram.com/taylorswift)
Rumors about a romance between the pop diva and the 35-year-old NFL Kansas City Chiefs player surfaced back in the fall of 2023, when paparazzi first photographed them together at New York's Nobu restaurant, where the couple held hands.
Soon after, the pair no longer hid their relationship: the singer was often seen in the stands during Kelce's games, supporting him together with family and friends.
And in return, the football player appeared at Swift’s concerts, openly showing his affection.