Taylor Swift is a superstar in her own right, but it would be wrong to say her dating history hasn’t played a huge part in her celebrity appeal. Fans and detractors alike have clung to the ups-and-downs of her relationships, with Swift building us up and breaking our hearts through her music. Swift has drawn on her love life to pen her (soon to be) 12 studio albums, tracking her relationships with famous faces, like Joe Alwyn, Harry Styles, Jake Gyllenhaal, John Mayer, and, her now-fiance Travis Kelce.
With the engagement news coming to light in late August 2025, fans are looking back at the ones who got away. Eyes are on her most-recent long-term ex, Joe Alwyn, who Taylor famously wrote about not wanting to marry her. Yikes.
Get to know the lore as we walk back through all of Taylor Swift’s ex-boyfriends and the songs she wrote about them.
A Complete History Of Taylor Swift’s Ex Boyfriends
Click to find your favourite:
- Joe Jonas
- Taylor Lautner
- John Mayer
- Jake Gyllenhaal
- Conor Kennedy
- Harry Styles
- Calvin Harris
- Tom Hiddleston
- Joe Alwyn
- Matty Healy
- Travis Kelce
Joe Jonas, July 2008 – October 2008
The first time Tay openly dated a celeb was her relationship with former Jonas brother Joe Jonas in 2008. Taylor later revealed the relationship was ended by Joe over a 27-second phone call. Yikes. 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 reportedly 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 John Mayer, and it was one of her most tumultuous relationships, per Swiftie lore. 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, and many believe was a call back to the relationship. 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
Taylor and Jake dated for four months, and Jake even got a private jet to bring her to him for a date. What sounded like a quick burn, the pair didn’t date for long, but as Taylor asked on All Too Well (10 minute version), “Did the twin flame bruise paint you blue?” The dual Sagittarians had an intsense love affair, despite a 10 year age gap, which fans think is the reason the two eventually called it quits.
Swift’s relationship with Gyllenhaal led to one of her all-time most famous songs All Too Well, which was later re-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 – 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 – 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.”
As the story goes, the two have been together ever since, and got engaged in August 2025. It looks like this one is forever.
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