Taylor Swift's Ex-Boyfriend & Dating History: 5 Fast Facts – Heavy.com

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Taylor Swift and Kansas City Chiefs tight end Travis Kelce have been dating for more than six months.
Throughout football season, Swift has been in the stands to support her main squeeze. At the Conference Championship game, Swift made her way down to the field to congratulate Kelce on the big win. The two shared some hugs and kisses as well as sweet words that included an “I love you” or two.
Prior to falling in love with Kelce, Swift dated quite a few men, including some of Hollywood’s hottest: from Jake Gyllenhaal to Taylor Lautner. She has also dated musicians like Harry Styles and world-renowned DJ Calvin Harris.
Swift is 34 years old and has never been engaged or married.
Here’s what you need to know:

Joe Alwyn


Swift and Alwyn, 28, were first linked in 2016. The two dated quietly without anyone catching on until a few months in. At the time, The Sun reported that Swift had been renting a place in London so that she and Alwyn could spend more time together.
At the beginning of her relationship with Alwyn, Swift took fairly drastic precautions to keep her relationship a secret. According to The Sun, she wore disguises (including the use of a wig) to meet her beau on several occasions.
Alwyn studied drama at the University of Bristol and London’s Royal Central School of Speech and Drama. He is an actor whose most notable role to date has been in the wartime drama, Billy Lynn’s Long Halftime Walk, which was released in 2016.
Not unlike her other relationships, Swift used her romance with Alwyn as inspiration for her music. On her album “Reputation,” fans believe that the songs “Ready For It,” “Gorgeous,” and “King of My Heart” were all written about Alwyn.
Swift and Alwyn’s split was confirmed by ET in April 2023.
In 2024, Swift is set to release a new album titled “The Tortured Poets Department,” and fans believe that details about her relationship with Alwyn — and it’s demise — will be sprinkled within the lyrics.

Taylor Swift


Swift and Harris first met at the Elle Style Awards in 2015 after being introduced by Ellie Goulding. They seemed to hit it off and began casually dating. It wasn’t until May, however, that the two made their relationship official, packing on the PDA at the Billboard Awards.
According to a relationship timeline posted by Cosmopolitan, the two stepped out together several times throughout the year.
Enter 2016 and Swift and Harris start getting more open about their romance.
“For the first time, I had the most amazing person to come home to when the spotlight went out and when the crowds were all gone,” Swift said during one of her acceptance speeches at the 2016 iHeart Radio Music Awards.
Flash forward just a couple of months and Swift is spotted out with British actor Tom Hiddleston. On June 3, 2016, Harris made his split from Swift official.
“The only truth is that a relationship came to an end & what remains is a huge amount of love and respect,” he tweeted at the time. Swift retweeted the message.
Swift dated Hiddleston packed on the PDA just about everywhere they went. The two broke up after just three months of dating — but evidently not on bad terms.
“Taylor is an amazing woman. She’s generous and kind and lovely, and we had the best time… Of course, it was real,” he told GQ after the split.
Many believe that Swift references her relationship with Harris in the music video for her song, “Look What You Made Me Do.”
You can watch the video below.

Jake Gyllenhaal

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Swift dated “Jarhead” actor Jake Gyllenhaal for a few months in late 2010. Things got hot and heavy between the two and many fans thought that this was it for Swift — that Gyllenhaal was “the one.” However, Swift is nine years younger than the actor and at age 20, she simply wasn’t ready to settle down.
The two were supposedly introduced by Gwyneth Paltrow and hit it off immediately. Sources say that Gyllenhaal pursued Swift but ultimately broke things off with her after just three months.
“One of the big reasons that Gyllenhall ended the relationship with Swift was because of the media attention. He wasn’t comfortable with all of the attention that they received and wanted to maintain a certain level of privacy. He also became less comfortable with their age difference, which became more apparent the more they continued to date,” Fame10 previously reported.
Swift and Gyllenhaal were spotted again in 2011, but their maybe-attempt at rekindling their romance didn’t go anywhere. She was linked to Conor Kennedy a few months later.
Of course, a Swift break-up wouldn’t be complete without a song or two — and Gyllenhaal was given the honors. According to People Magazine, there are (at least) two songs on Swift’s Red album that are believed to be about Gyllenhaal — “All Too Well” and “We Are Never Ever Getting Back Together.”
You can watch the video to the latter song below.

Taylor Swift boyfriend


Musician John Mayer has been a Hollywood playboy in his own right, dating stars from Jessica Simpson to Jennifer Aniston. And he also dated Taylor Swift. The two were first linked in 2009 — he was 32 and she was only 21.
The relationship between Mayer and Swift didn’t last very long — but Mayer still made a big enough impression on the country-turned-pop star that she wrote a song about him. “Dear John” is perhaps one of her most pointed tunes — and it’s no secret who the song is about, given its title.
Mayer spoke out about it in 2012.
“It made me feel terrible. Because I didn’t deserve it. I’m pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy thing for her to do,” Mayer told Rolling Stone.

Taylor Swift boyfriend


Early on in her career, Swift dated Joe Jonas. Their sweet relationship lasted from July 2008 until October 2008. It has long been rumored that Jonas ended his relationship with Swift with a “27-second-long phone call after meeting actress Camilla Belle,” whom he went on to date.
According to Billboard, Swift penned “Last Kiss” and “Forever and Always” with Jonas as her inspiration.
The two were able to get over their differences and remained friends after the split.
“She’s great. We’re friends. I think in this industry, you meet a lot of people and you stay in touch. Obviously, it’s tough to be friends with people that are always constantly traveling, but yeah, we’re cool,” Jonas told Access Hollywood back in 2015, according to MTV.
The following year (after her split from Jonas), Swift dated Twilight actor Taylor Lautner. The two met on the set of the film Valentine’s Day and really hit it off. While just about everyone was in love with Taylor & Taylor, things went south pretty quickly. However, this one probably wasn’t Lautner’s fault; in Swift’s song “Back to December,” she issues an apology to an ex — and fans believe that ex is Lautner.
“It was about a person who was incredible to me, just perfect to me in a relationship, and I was really careless with him. So this is a song full of words that I would say to him, that he deserves to hear,” Swift previously explained.
You can watch the music video below.
READ NEXT: Meet Joe Alwyn, Taylor Swift’s Boyfriend
Effie Orfanides has more than two decades of experience in entertainment journalism. She has been a contributor with Heavy since 2017 covering entertainment news. Effie is based in Tampa, Florida. More about Effie Orfanides
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