Taylor Swift’s Timeline Of Boyfriends

Taylor Swift is one of the few celebrities with little negative drama in her life. Although Taylor Swift does not have too much negativity in the press, she does get a lot of teasing for producing songs about her ex-boyfriends. So, who are Taylor Swift’s boyfriends she writes about? Here’s a list of Taylor Swift’s timeline of boyfriends:

 

Joe Jonas (2008)

In 2008, Swift was only beginning her reign of stardom. She was also beginning her timeline of boyfriends. Joe Jonas and Swift only dated for a few months before Jonas dumped her over the phone.

Swift immediately penned her hit “Forever and Always” shortly after the breakup. 

 

Taylor Lautner (2009)

Taylor met her next boyfriend on the set of the movie Valentine’s Day in 2009. The couple played young lovers in the movie.

The relationship only lasted a few months, and Swift wrote yet another song about the failed relationship. “Back In December” is presumed to be about their love.

 

Lucas Till (2009)

Swift never wrote a song about their relationship, but Lucas Till did star in one of her music videos. Till and Swift met on the set of “You Belong With Me” in 2009.

The relationship was brief, and the two eventually went their separate ways. 

 

John Mayer (2009)

John Mayer and Taylor Swift were also a couple in 2009. The couple started their relationship after writing a song together, “Half of My Heart,” which gained a lot of popularity on the Billboard charts.

The end of their relationship was incredibly devastating as Swift trashed Mayer in her song “Dear John.”

 

Cory Monteith (2010)

Swift never admitted to dating this Glee star in 2010. Although the two denied being an item, the couple was spotted together numerous times.

Swift never wrote a song about Monteith, so it is possible she was telling the truth.

 

Toby Hemingway (2010)

Toby Hemingway was another boy she never admitted dating in 2010. The two spent time together after they worked together on her music video, “Mine.”

Hemingway was another ex who was lucky enough to avoid the wrath of Swift’s songwriting revenge.

 

Jake Gyllenhaal (2010-2011)

Jake Gyllenhaal and Taylor Swift had a very brief romantic involvement. The couple was seeing each other from 2010 into early 2011.

Gyllenhaal was years older than Swift, and it is presumably the reason the couple went their separate ways. Swift’s new single, “We Are Never Ever Getting Back Together,” is believed to be written about him.

 

Zac Efron (2012)

If you haven’t noticed the pattern yet, Swift tends to date guys she has worked with within the music entertainment industry. Efron and Swift worked together on the set of the movie The Lorax in 2011.

The couple denied dating each other, but Swift has alluded to their brief romance in interviews.

 

Eddie Redmayne (2011-2012)

Swift and Redmayne started dating while she was auditioning to be in the movie Les Misérables. It was another brief relationship, and the couple went their separate ways.

Redmayne later admitted the “long-distance” wasn’t something he was ready for.

 

Conor Kennedy (2012)

Swift began dating the very young Connor Kennedy. Swift, at the time, was 22, and raised eyebrows after she decided to start dating the 18-year-old.

It was rumored she was trying to buy a home closer to Connor. However, after their split, we’re hoping she reconsidered that decision. Her album Red is believed to have a song written about Connor, “Everything Has Changed.”

 

Harry Styles (2012-2013)

Swift and One Direction star Harry Styles caused quite a stir when they were spotted together in New York’s Central Park in late 2012. The romance was short, and the couple split in January 2013. Fans still believe “Style” and “Out of the Woods” were inspired by their time together.

 

Calvin Harris (2015-2016)

Scottish DJ Calvin Harris dated Swift for just over a year before their split became public in June 2016. The two even celebrated their first anniversary with a tropical vacation.

Things got less sunny after the breakup. Swift’s team revealed she had co-written his Rihanna hit, “This Is What You Came For,” under the name Nils Sjöberg. Harris then took to Twitter to air his frustration with her team.

 

Tom Hiddleston (2016)

Tom Hiddleston’s summer romance with Swift lasted about three months, but it certainly didn’t go unnoticed. The actor even wore an “I ♥ T.S.” tank top at her Fourth of July party, which he later explained was a joke among friends.

The couple split in September 2016, though Hiddleston spoke warmly of her in a later interview.

 

Joe Alwyn (2016-2023)

With British actor Joe Alwyn, Swift kept much more of her love life to herself. They began dating in 2016, though the public didn’t find out until 2017, and stayed together for roughly six years.

Alwyn also helped write songs with her under the name William Bowery, including “Exile” and “Betty.” News of their breakup came in April 2023, shortly after her Eras Tour began.

 

Matty Healy (2023)

The 1975 frontman Matty Healy was linked to Swift in May 2023, when he turned up at her Eras Tour shows. By early June, reports said the pair had split.

Their brief romance gave fans plenty to discuss again when they linked songs on The Tortured Poets Department to him, though those connections remain speculation.

 

Travis Kelce (September 2023 – Present)

Travis Kelce caught Swift’s attention after sharing his failed attempt to give her a friendship bracelet with his phone number on it. By the time she appeared at his Kansas City Chiefs game in September 2023, the two were already dating.

The football star has since become her husband. Swift and Kelce married in July 2026 at Madison Square Garden, giving fans a wedding to talk about after years of cheering them on.

Title Image Courtesy: Soth Loeu via Wikimedia Commons