Taylor Swift’s Romantic History: Every Man She’s Loved & Lost, From Joe Jonas To Joe Alwyn

Taylor Swift has had a storied love life, one that's inspired her best music and a lot of media scrutiny. Now, we're taking a look back at the singer's romantic history!

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Taylor Swift is one of the most talked-about superstars in the world. Beloved by her longtime fanbase, and a fixture for media, the talented singer, 30, has been in the limelight ever since she appeared on the scene with her debut, self-titled album Taylor Swift, released in 2006. Over the years, Taylor has completely transformed how she uses her platform, just as she’s blended genres throughout her career.

One element of Taylor’s life that has continued to be the subject of so much attention is her love life. From her first public, high-profile relationship to her quiet romance with her current partner, Taylor’s love life has inspired music and fan fascination. Now, we’re taking a look back at Taylor’s romantic history over the course of her career!

Joe Jonas

Taylor Swift, Joe Jonas
Taylor Swift and Joe Jonas perform during ‘Jonas Brothers: The 3D Concert Experience’ [The Everett Collection].
Let’s take it all the way back to the summer and fall of 2008. Taylor was a rising star in the country music scene, with her debut, self-titled album and the anticipation for her second, Fearless. In the months leading up to the November release of her second studio album, Taylor started seeing Disney star Joe Jonas. The two were spotted out at events together, but their romance merely lasted a few months, from July 2008 to October 2008.

It’s now part of Taylor Swift lore that Joe broke up with Taylor over a phone call. But in the decade that has passed since the two were romantic, things seem to have become far more cordial between the two. Joe is now married to Game of Thrones alum Sophie Turner, and the couple welcomed their first child together, daughter Willa, in July 2020.

Lucas Till

Lucas Till, Taylor Swift
Lucas Till and Taylor Swift for ‘Hannah Montana: The Movie’ [The Everett Collection].
After dating Joe, Taylor had a short-lived fling with her “You Belong With Me” co-star Lucas Till. Besides having incredibly busy schedules as major rising stars in the spring of 2009, Taylor and Lucas were said to just be too good of friends to make their relationship anything beyond platonic. “We dated for a little bit. But, there was no friction because we were too nice,” Lucas said of his relationship with Taylor while chatting with MTV News.

“We just really both liked each other…[but] most relationships work out cause you get along and then you don’t, and then you make up and its passionate, and with us I really just liked her as a friend. That’s the only reason that didn’t work out.”

Taylor Lautner

Taylor Lautner, Taylor Swift
Taylor Swift and Taylor Lautner pictured leaving dinner at Benihana and heading over to Menchies Yogurt for some ice cream in Beverly Hills on Dec 2nd, 2009 [SplashNews].
Taylor’s next romance got a tad more complicated, but not due to any relationship drama. After meeting on the set of the 2010 ensemble comedy Valentine’s Day, Taylor Swift began dating her on-screen love interest Taylor Lautner. The pair dated for a few months between August 2009 and December 2009. It’s rumored that Swift went on to end the romance, with her song “Back To December” acting as a piece of closure for the singer and songwriter.

John Mayer

John Mayer, Taylor Swift
John Mayer and Taylor Swift perform together at the 2009 Z100 Jingle Ball at Madison Square Garden in New York on Friday, Dec. 11, 2009 [AP].
One of Taylor’s more infamous courtships came when she was in a three-month long relationship with singer John Mayer. At the time, Taylor was roughly 19 years old when she started dating the “Gravity” singer. The two collaborated on John’s tune “Half Of My Heart,” but the melody of their love song quickly went flat.

After the two split, Taylor addressed the relationship outright with her song “Dear John,” which included lyrics like, “Don’t you think 19 is too young to be played by your dark twisted games, when I loved you so?” The two haven’t been particularly friendly since, but Taylor moved on from the romance months later.

Jake Gyllenhaal

Taylor Swift, Jake Gyllenhaal
Taylor Swift and Jake Gyllenhaal dated for a few months between October 2010 and January 2011 [AP].
Between October 2010 – January 2011, Taylor was reportedly in a relationship with actor Jake Gyllenhaal. The relationship was fairly quiet, but there were occasions when the one-time couple was spotted out and about in New York City. By New Year’s Eve, though, the two went their separate ways, but Taylor seemingly left something behind from the relationship.

Taylor’s song “All Too Well” is said to be about her romance with the Brokeback Mountain actor. Plus, the lyrics also detail the infamous scarf that Taylor presumably left at the home of Jake’s sister, Maggie Gyllenhaal. “I walked through the door with you, the air was cold / But something ’bout it felt like home somehow and I / Left my scarf there at your sister’s house / And you still got it in your drawer even now,” the lyrics read.

Conor Kennedy

Taylor Swift, Conor Kennedy
Taylor Swift and Conor Kennedy dated from July-October 2012 [AP/SplashNews].
Months after her relationship with Jake ended, Taylor moved on to date a member of, what can only be described as, American royalty. From July – October 2012, Taylor was involved with Conor Kennedy. Their summer was one full of young love, with the two spotted enjoying time at Conor’s family estate, getting pizza, and even splashing around in the ocean. But as the temperatures chilled and summer turned to fall, so, too, did Taylor and Conor’s relationship. The couple broke up by October of that year.

Harry Styles

Taylor Swift, Harry Styles
Taylor swift and Harry Styles go to dinner at the Crosby Hotel in NYC Dec. 7, 2012 [SplashNews].
Between December 2012 and January 2013, Taylor Swift and Harry Styles were the “it” couple of the moment. The two only dated for just over a month, but their romance seemed to have enough packed into it for Taylor to write a number of songs inspired by their time together. Though the pair split in January, just weeks after New Year’s Day, there doesn’t appear to be any ill will between the two. And Harry is even flattered that Taylor wrote songs about their relationship.

“I think it’s, like, flattering,” Harry admitted to Howard Stern during his March 2020 appearance on The Howard Stern Show. “Even if the song isn’t that flattering, you still spent time on it and ultimately, using Taylor as an example, she’s a great songwriter. So they’re good songs.”

Calvin Harris

Calvin Harris, Taylor Swift
Taylor Swift and Calvin Harris are seen in New York City on May 26, 2015 [AP].
After years of relationships that barely lasted a few months, Taylor and Calvin Harris seemed to be like the perfect match. Taylor began dating the Scottish DJ, born Adam Richard Wiles, in March 2015, after their mutual pal Ellie Goulding introduced them at the February 2015 Elle Style Awards. Taylor’s romance with Calvin was full of cute PDA moments, and even a few award speech shout-outs.

But just after celebrating their one-year anniversary, Taylor and Calvin’s relationship ended in June 2016. Though the split seemed amicable at first, Calvin was none too please about Taylor’s quick rebound with her next love. The DJ seemingly “snapped” on social media, taking down his tweet saying that their split was completely respectful.

Tom Hiddleston 

Taylor Swift, Tom Hiddleston
Taylor Swift and Tom Hiddleston are seen in Rome, Italy, on June 28, 2016 [AP].
Not long after breaking things off with Calvin, Taylor had a short-lived romance with British actor Tom Hiddleston. While the relationship didn’t last long, it definitely created a lot of media attention. The couple, who dated from June 2016-September 2016, had a PDA-filled fling, jetting off to Italy, New York City, England, and more dream locations. And who could forget their Rhode Island photo fest?

Since the relationship didn’t last long, a number of haters alleged that the two were simply putting on a show for the cameras. Tom, however, stepped up and shut the naysayers down in an interview with GQ. “Taylor is an amazing woman,” he told the outlet in 2017. “She’s generous and kind and lovely, and we had the best time. Of course it was real.”

Joe Alwyn 

Taylor Swift, Joe Alwyn
Taylor Swift and Joe Alwyn are seen here leaving the Tiffany & Vogue Fashion & Film BAFTA After Party held at Annabels in Mayfair, London, on February 11, 2019 [AP].
Finally, we come to Taylor’s current and longest lasting relationship. It’s not known when the “Lover” songstress began dating British actor Joe Alwyn, but some speculate it was roughly at the end of 2016. During this time, Taylor also completely stepped away from public life; she was not active on social media, barely any paparazzi photos of her were taken, and she rarely attended any events. But while her public life seemed to take a beat, the singer was writing a fresh love song with her new beau.

News finally broke in May 2017 that the two were, indeed, an item. Taylor and Joe, however, rarely discuss their relationship in public, something the Grammy-winner eluded to in her Netflix documentary, Miss Americana. A number of her songs, however, say everything fans need to know about the current standing Taylor’s relationship with Joe. Between tunes on Lover and folklore, Taylor and Joe seem to be going as steady as ever!

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