Pop and Country Diva Taylor Swift Immortalizes Her Exes in Song

Popular Songstress Chronicles Her Heartbreak with Music.

It’s nearly impossible to not have heard of 12-time Grammy award-winning American pop and country singer-songwriter Taylor Swift, especially since she started dating Kansas City Chiefs tight end, Travis Kelce. The love affair, which began on the down-low in July 2023 came to the attention of fans of both the NFL and the 34-year-old blonde hitmaker when she began to attend the Superbowl winner’s games in September of the same year.

Part of Swift’s lyrical fame relies upon her songs of heartbreak and youthful angst drawn from her romances with an assortment of handsome celebrities and longtime pals. Her relationship with Kelce seems solid, but at least 17 of her previous sweethearts have been immortalized by her in often chart-topping songs. Will Kelce be next?

Swift, who has been accused by 47-year-old former Boyzone singer Shane Lynch of performing satanic rituals during her shows, has an impressive lineup of humble and high-profile exes including but not limited to Jonas Brothers singer Joe Jonas, Glee performer Cory Monteith, Taylor Lautner of Twilight fame, John F. Kennedy’s grandson Conor Kennedy, singer Harry Styles, and Brokeback Mountain star Jake Gyllenhaal. All of them, including Brandon Borello and Jordan Alford, have inspired compelling post-breakup songs that have propelled Swift to the status of billionaire, as of October 2023.

With so many great songs to choose from, which one was inspired by which romantic disaster?

In 2005, Swift was a freshman with fellow classmate and boyfriend named Jordan Alford. The first in a long line of brief but meaningful entanglements, things between them ended when Alford fell for Swift’s then-friend Chelsea. One of her first hits, “Picture to Burn,” which speaks of both sorrow and getting even, is believed to be dedicated to their relationship and his fickle affections.

The same year, Swift began to see Brandon Borello. So impressed was Swift by her beau that she wrote and performed “Our Song” at a talent show. With lyrics about whispered secrets and unauthorized get-togethers, it conveys a sweet and innocent excitement. Alas for their love, Borello decided to attend college, which inspired “Tim McGraw,” a song about upcoming separation.

Next in line was Sam Armstrong, said to be Swift’s first serious boyfriend. Their 2006 crush was marred by his tendency to cheat on her. Once again turning misery and profit, the brokenhearted songwriter penned “Should’ve Said No,” which deals with infidelity and betrayal and includes the words, “You should’ve thought twice ‘fore you let it all go.”

Swift then made headlines by dating fellow heartthrob Joe Jonas in 2008. As tradition was beginning to have it, their eventual split went deep and Swift confessed to Ellen DeGeneres on “The Ellen Show” that the end had been announced with a 27-second phone call. At 18, Swift penned “Forever and Always,” about a sweet love gone sour. In 2010, she went further with “Better Than Revenge,” in response to Jonas leaving her for actress Camilla Belle. In 2012, a friendship of sorts was able to develop after Jonas attended one of her concerts. “Holy Ground” tells the tale of an affectionate connection rebuilt.

While portraying an awkward and unpopular girl in the video for her 2009 hit “You Belong with Me,” she fell for co-star Lucas Till, who played a popular jock with a crush on her. Although she raved about the fun they had together and the excellence of his performance in her video, things didn’t last long. According to Till, the breakup was uneventful and the result of them each being too nice and developing a friendship instead of an ongoing love affair. Although “You Belong with Me” has nothing to do with them as a couple, it is interesting to know that it briefly led to them being one.

Not one to let moss grow under her tender heart, Swift took an interest in a werewolf later the same year. Twilight’s Taylor Lautner, to be exact. The two met during the filming of Valentine’s Day, which was Swift’s introduction to film acting. “Back to December” is believed by many to be a musical apology to Lautner for their breakup. Lautner had stood by silently while Kanye West interrupted his girlfriend’s Video Music Awards acceptance speech to praise Beyonce’s nominated video as superior.

Perhaps in hopes that an older man would be more compatible, the 19-year-old Swift began seeing 32-year-old singer John Mayer after he posted on Twitter in March 2009 that he wanted to collaborate with her. A year later their unexpected romance ended, and Swift released “Dear John,” a song about a young woman manipulated and mistreated. “Don’t you think I was too young to be messed with,” she sang. Mayer’s response to the song was not a positive one.

That spring, love once again bumped into Swift in the guise of Glee’s Cory Monteith. Love took flight less than a month later and inspired “Mine,” which reflects on the joy of a budding relationship. The song was later included in an episode of Glee, with Naya Rivera singing it. Swift ended 2010 by dating Jake Gyllenhaal, who had portrayed farmhand Jack Twist in the gay romantic tragedy Brokeback Mountain opposite Heath Ledger. After their five-month relationship ended because of the stress of constant press attention, Swift released the album Red, which included the catchy “We Are Never Ever Getting Back Together.”

Instead of getting back together with Gyllenhaal, Swift briefly dated Conor Kennedy during the summer of 2012. After his mother’s passing, Swift bought a $5 million house near his. Unfortunately for their love affair, this sudden decision to live so close to Kennedy unnerved him. Once their two-month relationship ended, she sold the house. Her song “Starlight” reflects on the romance of Kennedy’s grandparents, Ethel and Robert F. Kennedy.

Later that year, Swift and English singer Harry Styles began a five-month courtship that saw her refer to him in the song “Style” as having “that James Dean daydream look in your eye.” Unlike most of her previous romances, the two remain friends, as seen in their friendly 2021 Grammy Awards chat. Having had a taste of dating a non-American, Swift’s next flirtation was with Scottish DJ and singer Calvin Harris. They lasted a year, dating from early 2015 until June 2016.

Unlike her breakup with Styles, things did not go well when Swift and Harris called it quits over a collaborative disagreement. On Harris’s hit “This Is What You Came For,” Swift sang under a pseudonym. When she revealed that she was the previously unknown “Nils Sjoberg” Harris became enraged and publicly announced that he would never collaborate with her again. His reward was to inspire her to write “I Forgot That You Existed,” about her indifference to their past love, and “Look What You Made Me Do.”

She was not single long and was seen in June after her breakup with Harris kissing British actor Tom Hiddleston by her Rhode Island home. Things looked solid, with each of them meeting one another’s parents mere weeks after announcing their affair. This time it was Swift who could not bear the constant media attention and what she had hoped would end in marriage turned into a summer fling lasting only three months. Their whirlwind infatuation is believed to have been the inspiration for “Getaway Car,” a song about getting in too deep too fast.

When she took up with Joe Alwyn in 2016, things changed for Swift. The two first encountered one another at the Met Gala and this time she played her cards closer to her chest. Alwyn likewise stayed silent about their involvement until 2018. During COVID-19 seclusion, they lived together as a couple, and they remained as such until 2023. Although “Dress” hints at their early times together, the mutual bond of creativity could not save them from growing apart. Songs including “Lover” and “Cruel Summer” tell the tale of a romance that went from spark to a more enduring form of love.

Now involved with NFL player Travis Kelce, who does not appear to be afraid of publicity, Swift does not seem to have written any songs about them yet, although she did mention him during her Eras Tour in November 2023 during a performance of “Karma,” when she changed the lyrics “Karma is the guy on the screen” to “Karma is the guy on the Chiefs.” Not bad for a guy who tried to get his phone number to the singer by giving her a friendship bracelet when he was in the Eras Tour audience in July 2023.