When you spend your early dating years living in the spotlight like Taylor Swift, your entire personal life becomes open for the world to see … and judge.
Swift began her career in Nashville as an ambitions 11-year-old, and she’s now a worldwide pop icon, millionaire, and philanthropist with a fan base of billions. But most of the time, all any one can talk about is who she happens to be dating at the moment.
Swift’s public dating life has been the subject of cruelty and speculation for the past decade, yet she always manages to rise above the chatter and put on an amazing show for her Swifties. That’s admirable, and my hat is off to her! After all, who among us hasn’t kissed a few frogs (and outright toads) while searching for our own Charming someone? Swift certainly has, and since the press was around to capture every nitty gritty detail of her past ten relationships (at least), we’ve got a pretty good idea of which boyfriend was “trouble when [he] walked in” and which is a real “Love Story.” We’ve listed them out below.
10. John Mayer
When they dated: From November 2009 to February 2010
Why he’s the worst: In 2010, John Mayer was fully in his “sleep with anyone who moves” phase while also letting some very questionable opinions slip to the media. I’m not going to go into details of why John Mayer is, in general, a bad boyfriend. We all remember the 2010 Playboy interview in which Mayer shared details of what Jessica Simpson was like in bed (“sexual napalm”), dropped the “N” word, boasted “there have probably been days when I saw 300 vaginas before I got out of bed,” and called his own penis a “white supremacist.” A real Prince Charming, eh?
Also, did we mention the age gap? Mayer was 32 and Swift was 19 when they dated. That age difference and other infractions made their way onto Swift’s 2010 album Speak Now, most notably on the aptly-named track “Dear John.”
9. Matty Healy
When they dated: For one month in May 2023
Why he’s the worst: Matty Healy is the lead singer of the band 1975. The media picked up on a fling they had in May 2023, but by the time Swifties fully caught wind … it was already over. In hindsight, this was clearly a rebound from her breakup with Joe Alwyn, whom she dated for six years. As for why the bad boy rockstar is among the worst, it’s simply that he’s just a blip on the radar, yet in that short time he did quite a bit of damage to Swift’s mental health—and his many controversies, separate from Taylor Swift, attracted significant backlash.
We got a taste of how toxic their brief time together was when Swift released The Tortured Poets Department in 2024, which took solid aim at Healy. She even wrote a song for him called “The Smallest Man Who Ever Lived.” Ouch!
8. Joe Alwyn
When they dated: May 2017 through March 2023
Why he’s the worst: British actor Joe Alwyn and Swift dated for six long years while keeping a relatively low profile. They avoided paparazzi almost entirely for the first few years, gradually being photographed together more as time went on but never revealing too much. Their relationship was the inspiration for many of her songs, and Swift admitted in 2020 that Alwyn even co-wrote two songs from her folklore, evermore, and Midnights albums under the pseudonym William Bowery.
Alwyn isn’t the worst guy, and it seems that the couple just grew apart and didn’t see a future together. The fact that Swift didn’t retaliate with a revenge track after their 2023 breakup (she saved those for “Ratty” Healy) speaks volumes.
7. Calvin Harris
When they dated: March 2015 to June 2016
Why he’s the worst: DJ and producer Calvin Harris and Taylor Swift were together for over a year, and unfortunately their very ugly breakup played out in the public eye. After they split in June 2016, Harris called Swift out on Twitter after hearing a media report that she’d penned his biggest hit, “This Is What You Came For.” Harris accused Swift, who had already moved on to actor Tom Hiddleston, of trying to “tear your ex bf down for something to do.” He has since deleted the tweets and apologized for his reaction. Swifties believe Swift’s song “I Forgot That You Existed” is about Harris, and I’m inclined to agree.
6. Jake Gyllenhaal
When they dated: October 2010 to January 2011
Why he’s the worst: This was one of Swift’s briefest flings, but one of the most memorable for her fans. Her time with actor Jake Gyllenhaal is also said to have inspired a number of breakup songs, especially the epic “We Are Never Ever Getting Back Together.”
Gyllenhaal was another older boyfriend; he was 29 to her 20, and he was just as big of a star as she was at that time. He reportedly made big romantic gestures like renting out a movie theater for a private screening of a Disney film and flying Swift to London just to spend one day together. It all seemed so romantic, but then it was over before you can say “All Too Well.”
5. Joe Jonas
When they dated: July to October 2008
Why he’s in the middle: Okay, Joe Jonas is right in the middle of this list, because he wasn’t really that bad of a boyfriend for Swift except for the way they broke up. Yes, friends; Jonas broke up with Swift by leaving her a 27-second voicemail. Oof.
Their relationship lasted just a few months, but it inspired breakup songs written by both artists. Swift inked “Forever and Always” and “Last Kiss” about Jonas, and later released another pointed tune called “Mr. Perfectly Fine” on Fearless Taylor’s Version. All these years later, the two are no longer enemies and are almost friendly.
4. Tom Hiddleston
When they dated: May to September 2016
Why he’s in the fourth spot: We just like Tom Hiddleston, okay? He’s a likable enough actor, and he and Swift enjoyed a brief but very public fling for a few months in 2016. They met at the Met Gala, where Swift was co-hosting sans her date, then-boyfriend Calvin Harris. The two went viral dancing to T.I.’s “Bring ‘Em Out,” and by June Harris was out and Hiddleswift was happening.
There were ample photos of the couple canoodling from California to Italy, and they spent a fun Independence Day weekend with all of her friends. He even met her parents! Alas, it was not meant to be, and after three months they called it quits. According to E!, Swift ended it because he “wanted to take the relationship to be too public.”
3. Taylor Lautner
When they dated: August to November 2009
Why he’s the pretty okay: Taylor Lautner seems like a pretty chill guy, and this brief relationship with Swift was as vanilla they come. They simply ran out of chemistry and called it quits. There was no drama, no manipulation, no revenge songs. Nada. These days, Lautner and his wife, Taylor Lautner (that will never not be funny), are even self-proclaimed Swifties.
2. Harry Styles
When they dated: December 2012 to January 2013
Why he’s pretty good: They were only together for a month or so, but look at all the songs she got out of it! Swift dated Styles when he was at the height of his One Direction fame. They had a highly publicized fling that some believed was just a publicity stunt for both artists, but at the end of the day, they ended things with minimal drama. Swift went on to bless the world with songs inspired by Styles like “Out of the Woods,” “I Knew You Were Trouble,” and of course, “Styles.”
1. Travis Kelce
When they dated: September 2023 to present
Why he’s the best: Kansas City Chiefs tight end Travis Kelce marks the end of Swift’s musician/actor era! Her fans were confused at first, but quickly saw the beauty of the girl “in the bleachers” winning over the big, burly football star. It all started when Kelce went to see her Eras tour and said he was disappointed he didn’t get to speak with her. Next thing you know, they’re dating and she’s turning up dressed in Kansas City gears at lots of his games. They’ve now been together for about a year, and they’re still supporting each other in the sweetest way. Honestly, I’m rooting for them!
Published: Jul 24, 2024 04:02 pm