A comprehensive history of Taylor Swift's famous exes

Taylor Swift is one of the most successful and popular singers in the world and she is also infamous for her dating history. The Grammy winner has been romantically linked to many famous men over the years, some of whom inspired her best songs. But who are the lucky guys who have dated Taylor, and how do they compare to each other? Here is our ranking of Taylor Swift’s famous boyfriends, from worst to best.

Joe Jonas and Taylor Swift dated for about three months in 2008, but their relationship ended in a very unpleasant way too. Swift revealed on The Ellen DeGeneres Show that Jonas broke up with her over the phone in 25 seconds. She also wrote songs about him, such as “Forever & Always”, “Last Kiss”, and “Mr. Perfectly Fine”. Jonas later apologized for the way he handled the breakup and said he and Swift are now friends.

Crowned Taylor swift's best ex, Taylor Lautner and Taylor Swift met on the set of the movie Valentine’s Day, in which Swift had a cameo and were seen getting cozy on the set while filming. They dated for a few months in 2009 and 2010, but they broke up and this time it was Taylor Swift who did the deed. Lautner was silent on his part about the break up and kept mum when asked questions about her. Swift reportedly wrote the song “Back to December” about Lautner, apologizing for the way she treated him. The two have remained friends over the years, and Lautner even joined Swift on stage at her Eras Tour with his wife tagging along, who funnily enough also sports the name Taylor.

John Mayer and Taylor Swift dated for a few months in 2009 and 2010, but their relationship ended badly. Their age was simply too much with a 19-year-old swift dating a 34-year-old Mayer. Swift reportedly wrote the song “Dear John” about Mayer, accusing him of playing with her emotions and breaking her heart. Mayer later said he felt “humiliated” by the song and called it “cheap songwriting”. He also wrote a song called “Paper Doll” that was rumored to be about Swift. The two singers have not been on good terms since their breakup.

Jake Gyllenhaal and Taylor Swift had a brief but intense romance in 2010 and 2011. They were spotted spending Thanksgiving together, but their relationship fizzled out after a few months. Swift allegedly wrote several songs about Gyllenhaal, including “All Too Well”, “We Are Never Ever Getting Back Together”, and “The Last Time”. Fans have speculated that Gyllenhaal broke up with Swift over the phone and did not return her scarf that she left at his sister’s house.

Conor Kennedy of the Kennedy dynasty fame and Taylor Swift had a summer fling in 2012. They met at the Kennedy compound in Hyannis Port, Massachusetts, and Swift even bought a house near his while they were dating. They were seen sailing, swimming, and kissing on the beach. However, their relationship ended in October 2012, reportedly due to their busy schedules and the distance. Swift allegedly wrote the song “Begin Again” about Kennedy, describing how he made her feel hopeful after a bad breakup.

Harry Styles and Taylor Swift dated on and off for a few months in 2012 and 2014 and were all the rage at the time; their shippers were insane about them. They were seen holding hands in New York City, skiing in Utah, and kissing in Times Square on New Year’s Eve. However, their relationship was also plagued by rumors, drama, and paparazzi. Swift reportedly wrote several songs about Styles, including “Style”, “Out of the Woods”, and “I Knew You Were Trouble”. Styles also wrote songs about Swift, such as “Two Ghosts” and “Ever Since New York”.

Calvin Harris and Taylor Swift were one of the hottest couples in music in 2015 and 2016. They dated for over a year and seemed very happy together. They even collaborated on the song “This Is What You Came For”, which Swift co-wrote under a pseudonym. However, their relationship ended in June 2016, and things got messy afterward. Harris accused Swift of trying to make him look bad by revealing her involvement in the song, and he also hinted that she cheated on him with Tom Hiddleston. Swift reportedly wrote the song “I Did Something Bad” about Harris.

Tom Hiddleston and Taylor Swift had a whirlwind romance in 2016, shortly after she broke up with Calvin Harris. They were seen traveling the world together, and Hiddleston even wore a “I <3 TS” shirt at a Fourth of July party. However, their relationship only lasted for three months, and some people speculated that it was a publicity stunt. Swift allegedly wrote the song “Getaway Car” about Hiddleston, comparing their relationship to a doomed escape plan.

Joe Alwyn was the person that Taylor had the longest and most serious relationship. They started dating in late 2016, but they kept their relationship very private and low-key. They rarely made public appearances together, and did not talk about each other in interviews. They also avoided posting about each other on social media, except for a few subtle hints. While living together in London, they supported each others careers and were a steady, if quite duo. Swift wrote many songs about Alwyn, such as “Lover”, “Delicate”, “Call It What You Want”, and “Willow”. Alwyn also co-wrote some songs with Swift under the pseudonym William Bowery, such as “Exile” and “Betty”. Unfortunately, their relationship ended in July 2023, due to irreconcilable differences; devastating Swifties worldwide. Swift and Alwyn released a joint statement saying that they still love and respect each other, and they asked for privacy during this difficult time.

Kansas City Chiefs' Travis Kelce and Taylor Swift are the hottest newest couple in the celebrity world. They met at a charity event in September 2023, and they hit it off immediately. They have been seen attending each other’s games and concerts, and they have been very supportive of each other on social media. They are both very successful and talented in their respective fields, and they seem to have a lot in common. Fans are already shipping them as “Traylor” and hoping they will last.