Taylor Swift discusses her music video "All Too Well" at Toronto film fest, in Toronto


  • Taylor Swift's career as a musician spans almost two decades
  • She matured from a 16-year-old country singer to a multi-awarded performer
  • Her latest relationship, which lasted six years, reportedly ended this April 2023

Taylor Swift's career as a musician spans almost two decades, with her style of music changing as she grew up and matured from the 16-year-old "Tim McGraw" singer to a highly-accomplished performer with 540 awards to her name. She has cultivated a loyal fanbase and earned a group of friends in the industry, who sometimes make cameos in her highly-anticipated music videos.

A well-regarded lyricist, Swift is known for writing about her life, including songs inspired by her love life or stories she has crafted at her peak creativity. Along with the rise of her success came a growing interest in her dating life. With reports of the end of her six-year relationship with Joe Alwyn surfacing this April, fans are waiting for official confirmation from the couple.

For now, let's take a look at her dating timeline according to media outlets:


Joe Jonas (July-October 2008)

Joe Jonas
Getty Images/John Lamparski

One-third of the Jonas Brothers, Joe was linked to Taylor Swift back in 2008, with Us Weekly reporting that the Disney heartthrob ended the relationship in a 27-second phone call in October of that year. Joe Jonas is now married to "Game of Thrones" star Sophie Turner.


Taylor Lautner (September-December 2009)

Charley Gallay/Getty Images for Breeders' Cup

Taylor Lautner and Taylor Swift were co-stars in the movie "Valentine's Day" where they played high school sweethearts in 2009. Lautner presented Swift with the Best Female Video award at the 2009 MTV Video Music Awards, a moment that has gone down in history when Kanye West cut off Swift's acceptance speech. According to Lautner, he first thought the situation was part of a "rehearsed" kit.

"He jumped off, she finished [and] the second she turned back around, and I saw her face for the first time, I was like, 'Oh. No, that wasn't good. Probably should've said something,'" Lautner told "The Squeeze" podcast.


Lucas Till (2009)

macgyver s4 news
Jace Downs/CBS

Lucas Till starred in "Hannah Montana: The Movie" in 2009, where Swift made a cameo to sing "Crazier." Till then made an appearance in Swift's 2009 music video for "You Belong With Me." He has also joined the cast of the X-Men franchise, starring in "X-Men: First Class," "X-Men: Days of Future Past" and "X-Men: Apocalypse."


John Mayer (November 2009-February 2010)

John Mayer
Reuters/Mario Anzuoni

Mayer and Swift got linked after being spotted at a Nashville Bistro Cabana in January 2010. This came after they wrote the song "Half of My Heart" for Mayer's album "Battle Studies." It was a friendly gathering of about 15 friends, a source told People.


Cory Monteith (2010)

Cory Monteith

Monteith and Swift were seen hanging out in March 2010 at Pinz Bowling Alley. They were also seen together at the January Grammy Party and a late-night dinner in February 2011. Monteith, who was most popular for his role in "Glee" alongside Lea Michele, passed away in July 2013.


Jake Gyllenhaal (October-December 2010)

Jake Gyllenhaal leads the cast in the English version of 'Strange World', due for release in November

Gyllenhaal and Swift dated for two months, with some seeing them together at a broadcast of "Saturday Night Live" in Manhattan in October before Gyllenhaal broke things off right around New Year's in 2010. Gyllenhaal's movie credits span the spectrum of big-budget projects to small-screen gems, including "Everest," "Okja," "Nocturnal Animals," "Donnie Darko" and "Brokeback Mountain."


Adam Young (2010)

Though the two never officially dated, the subject of one of Swift's most famous songs, "Enchanted," is Owl City singer Adam Young, whom she had a crush on and exchanged emails with. Young penned his own "Enchanted" love song for Swift on Valentine's Day, including lyrics such as "I was never in love with someone else" in reply to her "Please don't be in love with someone else" lyrics.


Conor Kennedy (July-September 2012)

Jason Kempin/Getty Images

Conor Kennedy, the grandson of former U.S. Senator and Attorney General Robert F. Kennedy, was linked to Swift in 2012 after the two were repeatedly spotted around the Kennedy compound in Hyannis Port, Massachusetts. In October 2022, Kennedy revealed via Instagram that he joined Ukraine's International Legion of foreign fighters. "Going in, I had no prior military experience and wasn't a great shot, but I could carry heavy things and learned fast. I was also willing to die there," he said.


Harry Styles (December 2012-January 2013)

Harry Styles
Tolga Akmen/AFP via Getty Images

Harry Styles and Taylor Swift were spotted at the Central Park Zoo in December 2012, sparking rumors that the two were dating. Styles, who began his music career as part of One Direction, is currently in the middle of his Love on Tour concert series. He has also embarked on acting, starring in "Dunkirk" and, more recently, in "Don't Worry Darling."


Calvin Harris (March 2015-June 2016)

Calvin Harris
Getty Images

The Scottish DJ met Swift backstage at the 2015 Brit Awards. Swift talked about their relationship in Vogue, calling it a "magical relationship" she wanted to be "low-key." Harris is currently busy with his music, set to perform in Coachella 2023 this April. Other performers include Bad Bunny, BLACKPINK, Rosalía, Gorillaz and Burna Boy.


Tom Hiddleston (June-September 2016)

Tom Hiddleston
Rich Polk/Getty Images for Disney

Swift and Hiddleston were spotted kissing on Rhode Island in June 2016. "Tom wanted the relationship to be more public than she was comfortable with," a source told Us Weekly. This prompted Swift to end the relationship after three months. Talking to GQ in 2017, Hiddleston, famous for playing the role of Loki in the Marvel Cinematic Universe, said, "Taylor is an amazing woman. She's generous and kind and lovely, and we had the best time."


Joe Alwyn (2017-2023)

Joe Alwyn
Jamie McCarthy/Getty Images

Alwyn and Swift have been a unified front in keeping their relationship private, which makes the start of their relationship hard to pin down. According to reports that surfaced in May 2017, they had been together for months, and their family and friends knew. Alwyn is an English actor and songwriter. Under the pseudonym William Bowery, he penned "Betty" and "Exile" alongside Swift for her 2020 album, "Folklore."

The exact end of their relationship is also undetermined. Page Six reached out to representatives of both parties, but nobody replied.