Taylor Swift revelation: Ranking pop superstar’s ex-boyfriends from worst to best

taylor-swift-revelation-ranking-pop-superstars-ex-boyfriends-from-worst-to-best NEW YORK, NY - MAY 05: Singer Taylor Swift attends the "Charles James: Beyond Fashion" Costume Institute Gala at the Metropolitan Museum of Art on May 5, 2014 in New York City. (Photo by Andrew H. Walker/Getty Images)

Taylor Swift is known for turning her ex-boyfriends into poetic inspirations and channelling all of her heartbreaks into works of art aside from her pop star darling persona.

Swift has been in the music industry for over a decade, which means she has a library of award-winning songs inspired by her ex-boyfriends or brief flings.

That being said, these are Taylor Swift’s five most publicized relationships, rated from worst to finest.


Joe Jonas (July 2008-October 2008)

We ranked the former Jonas Brother member as the “worst” ex at the bottom. This comes after the Grammy Award winner said in an interview with Ellen DeGeneres in 2008 that Joe ended their relationship over a 27-second phone call.

Taylor Swift told Ellen DeGeneres:

“When I find the right guy for me, he’ll be wonderful, and when I look at that person, I won’t even remember the kid who broke up with me over the phone in 25 seconds when I was 18.”

Unfortunately, Joe broke not only Taylor’s heart, but also the etiquette of breaking up in person.

Calvin Harris (March 2015 to June 2016)

They met at the Brit Awards in February 2015 through a common acquaintance, Ellie Goulding. Taylor Swift and the Scottish DJ called it quits after a year of dating, resulting in a dramatic split.

This prompted Harris to go on a Twitter rampage, writing:

“I assume if you’re happy with your new relationship, you should focus on that instead of trying to knock down your ex-BF for something to do.”

Harris’ best buddy, John Newman, even termed their split “brutal,” while one of Swift’s renowned pals, Lena Dunham, referred to the DJ as her “worst ex-boyfriend.”


Tom Hiddleston (June 2016-September 2016)

Just weeks, if not days, following her public separation from the EDM artist, the pop diva was spotted dancing with Tom Hiddleston at a Met Gala after-party in 2016.

The “Hiddleswift” was created after the couple was seen kissing and snuggling near her Rhode Island home.

Hiddleston even consented to wear the classic “I Heart T.S.” shirt when the two of them celebrated Independence Day. That’s a great boyfriend!

Jake Gyllenhaal (October 2010-January 2011)

Taylor Swift’s relationship with Jake Gyllenhaal, like her previous ones, had a significant age difference. The actor was 29 at the time, while the pop singer was barely 20.

According to Us Weekly, the “Brokeback Mountain” star informed Swift that their relationship “wasn’t working out” and that, while she was mature for her age, “she was so naive she didn’t know how to cope with it.”

Jake, on the other hand, revealed that he actually “cares for her,” but dating the “Bad Blood” musician was too much for him because he prefers to keep his personal life secret.

Harry Styles (December 2012-January 2013)

Ed Sheeran, a mutual friend and fellow artist, introduced the two. Despite the fact that their romance was brief, it remains one of the most talked-about celebrity partnerships.

In an earlier interview with Rolling Stone, he called his relationship with her as “challenging” but a “learning experience.” Taylor Swift, on the other hand, seemed to agree and echoed the same sentiment in a 2017 Billboard interview.

A source told Us Weekly in 2014 that the couple “had become buddies” after a year of separation.