Taylor Swift is a superstar in her own right, having released 10 studio albums and re-recorded many of her previous albums under the ‘Taylor’s Version’ moniker. The star is currently completing her sold-out, billion dollar Eras Tour across the world, but fans still have their eyes firmly placed on who the 33 year-old starlet is dating in the meantime (and Swift’s ex-boyfriends).
While Taylor is currently dating Kansas City Chiefs football player, Travis Kelce, we’re yet to receive an album of insights into their growing romance. So, for now, we’ll have to review Swift’s extensive catalogue of music to get lost in all the emotions of her relationships’ past.
With an illustrious dating history spanning all matter of men from Jake Gyllenhaal to John Mayer, Harry Styles to Calvin Harris, here we take a walk back through all Taylor Swift’s ex-boyfriends and the songs she wrote about them.
Joe Jonas, July 2008 – October 2008
The first time Tay openly dated a celeb was her relationship with former Jonas brother Joe Jonas, now lead frontman of DNCE, in 2008. The relationship was ended by Joe over a 27-second phone call. She ended up writing the song “Forever And Always” about him. On Speak Now she also wrote ‘Last Kiss’ and later released ‘Mr. Perfectly Fine’ as a Vault track on Fearless.
Taylor Lautner, August 2009 – November 2009
The pair met on the set of Valentine’s Day and took an instant liking to one another. Taylor wrote the song ‘Back To December’ about regretting breaking up with Lautner.
It features the lyrics “your tanned skin, your sweet smile”, which tipped fans off it was Lautner.
The two have remained friends and he appeared on stage at her Eras Tour concert to announce the launch of Speak Now (Taylor’s Version).
John Mayer, November 2009 – February 2010
Taylor was only 19 when she dated the singer, and it was one of her most tumultuous relationships. They wrote ‘Half Of My Heart’ together, but she later ended up writing the song Dear John about him, a song about a man breaking the heart of a girl who was too young to know better.
Mayer is rumoured to have retaliated with his song ‘Paper Doll’.
Swift released ‘Would’ve, Could’ve, Should’ve’ on Midnights, which offered references to Dear John. The song features the heart-breaking lyric, “I damn sure never would have danced with the devil, at 19.”
Jake Gyllenhaal, October 2010 – January 2011
Tay and Jake dated for four months, and Jake even got a private jet to bring her to him for a date. The pair had a 10 year age gap, which fans think is the reason the two eventually called it quite.
Swift’s relationship with Gyllenhaal led to one of her all-time most famous songs All Too Well, which was later released as a 10 minute version on Red (Taylor’s Version). The song suggests that after the two had called it quits Gyllenhaal had called to rekindle things, but that the relationship was already too broken.
Conor Kennedy, July 2012 – September 2012
Taylor and Conor had a fling over summer, but Conor was only 18 at the time and headed for college. She received some criticism for the age difference between the two.
During this time she purchased a home near the Kennedy compound in Massachusetts, but the two couldn’t make it work. Things got worse when Connor’s family accused him and swift of crashing his cousin’s wedding in August.
It is believed the star wrote ‘Begin Again’ about Kennedy, talking about how meeting someone like him helped her forget dating traumas of the past.
Harry Styles, December 2012 – January 2013
This short-lived relationship was very popular for their fans. They broke up due to the intense media attention they were subjected to.
It is believed that most of 1989 is about Styles, including ‘Style’ and ‘Out Of The Woods’. Many think ‘I Knew You Were Trouble’ on Red is also about him.
The two have since seemed supportive of one another, with Swift giving Styles a standing ovation when he won a Grammy in 2023.
Calvin Harris, March 2015 – June 2016.
Taylor’s relationship with Calvin was her longest to date, at this point in time. While the pair seemed to be doing great, the distance and their clashing schedules eventually got to them, and they broke up.
Swift and Calvin Harris co-wrote hit ‘This Is What You Came For’ together, with Swift originally going by a pseudonym. This became a source of tension in the relationship, and it was left in bitterness.
The only song Swift has appeared to write about Harris is ‘I Forgot That You Existed’.
However, on the release of Midnights, many fans think that ‘High Infidelity’ is about Harris, featuring the lyric, “Put on your headphones and burn my city. Your picket fence is sharp as knives and I was dancing around it.”
Tom Hiddleston, June 2016 – September 2016
Tom Hiddleston and Taylor Swift met at the 2016 Met Gala and then were spotted kissing near the beach in June 2016 – very soon after Tay and Calvin’s breakup.
Their whirlwind romance quickly saw them jetting across the road and making grand gestures of love (namely via a t-shirt that read ‘I heart TS). Alas however it wasn’t to last and the pair have since gone their separate ways. “It was an amicable split,” a source told WHO. RIP Hiddleswift.
Joe Alwyn, Early 2017 – 2023
Although Taylor had been open about her romances in the past, it appears she went the opposite way with British actor Joe Alwyn.
The pair were famously reclusive over their six year romance. They met on the same night that she met Hiddleston, the Met Gala. The two began a relationship after her time with Hiddleston came to an end, per ‘Delicate’, she would meet him in dive bars in New York City.
Things started off casual (see: ‘Cruel Summer’), but they couldn’t deny their feelings for one another. The two went on to have a beautiful and lasting relationship, even writing songs together such as ‘Exile’, ‘Evermore’ and ‘Sweet Nothing’. Alwyn was credited under a pseudonym ‘William Bowery’.
In 2019, the pair sparked engagement rumours, with some reports even alleging that they were looking to purchase a joint property in London. However, in April 2023 it all came to an end with the pair rumoured to have called it quits.
While they never made an official statement, Swift did release the song ‘You’re Losing Me’, alleged to be about the breakup. It features the heart-breaking line, “And I wouldn’t marry me either, a pathological people pleaser, who only wanted you to see her.”
However, sources told ET that the split was “not dramatic” and that the relationship had simply “run its course”.
Matty Healy, May 2023
In May 2023, Swift was rumoured to be dating the 1975 front man Matty Healy, much to the chagrin of her fans who did not approve of the singer as a love interest.
The pair were seen exiting her Nashville concert together and at dinner several times, but it appears the two called it quits within a month or so.
Travis Kelce, September 2023 – Present
In September 2023, Swift was rumoured to be in a relationship with Chiefs NFL star Travis Kelce. Kelce told fans on his New Heights podcast that he had wanted to give Swift a a friendship bracelet with his phone number on it when he attended the Kansas City dates for the Eras Tour. However, none of the celebrities got to meet Swift after the show, so he didn’t get to share it with her.
“She doesn’t meet anybody, or at least she didn’t want to meet me,” he joked. “I took it personal.”
Then came rumours from DeuxMoi that Swift had been spotted with Kelce. The Messenger reported on a source that said, “Taylor and Travis have been quietly hanging out. “She saw him when she was in NYC a few weeks ago.”
While Swift is a known supporter of the Philadelphia Eagles, she was spotted in a box supporting the Chiefs (wearing their merchandise) sitting right next to Travis Kelce’s mum on September 24.
Since then, Swift and Kelce have dating, with Swift attending 13 of Kelce’s games, including the Super Bowl (which he won). Things appear to be quite serious—with the two spending plenty of time with each other’s family and friends, and even sharing a smooches in public. They’ve holidayed in the Bahamas, attended Coachella together and even flown across the world to be with one another, so it seems they’re going from strength to strength.
