13 of Taylor Swift’s Boyfriends. Who’s Lasted the Longest?

Taylor looking coy Larry Busacca, Getty Images

Taylor Swift is one of the world’s leading contemporary recording artists known for her narrative songs about her personal life and receiving widespread media coverage. At the young age of only 29, Taylor Swift (or T-Swift, as her fans often call her), has experienced her fair share of heartbreak. Her relationships have long been famous for, on the most part, being very public. Swift’s personal life is the subject of constant media attention, and the speculation of which song is about which boyfriend has kept fans, celebrity blogs and shamers busy over the years.

In 2013, Abercrombie & Fitch marketed a slogan T-shirt with a “slut-shaming” remark directed toward her. The shirt in question read “#more boyfriends than t.s.,” a jab at Swift’s tumultuous love life. However, her fans – known as “Swifties” – are staunch and vocal defenders! The retailer was forced to pull the t-shirt after they swarmed the retailer with angry complaints. After incidents like this, and her widely ridiculed PDA with British actor Tom Hiddleston, the “in love with love” singer has gone low key, in her current not-so-public relationship with another British actor, Joe Alwyn. Is he the one? While we wait to find out, let’s take a little walk down memory lane.

Joe Jonas (July 2008-October 2008)

Joe Jonas
Jeff Kravitz, FilmMagic

The Grammy award-winning singer started her escapades with the opposite sex in her late teens when she hooked up with the handsome Joe Jonas of the pop-rock band the Jonas Brothers. Their three month old relationship hit the rocks in a 27-second phone call from Jonas. Swift’s song “Better Than Revenge” is believed to be targeted at the girl Jonas replaced her with.

Lucas Till (March 2009-April 2009)

Lucas Till

Swift met Lucas when they worked together in her 2009, “You Belong With Me” music video. The American actor is known mostly for his portrayal of the “Havok” character in the X-Men series. Not only was there insufficient drama in this short, two-month round of dating for him to have been left out of the song inspiration catalog, he later claimed they hadn’t worked out because he “really just liked her as a friend”. Diss!!!

Taylor Lautner (August 2009-December 2009)

Taylor Lautner
Mark Davis, PictureGroup

Lautner is known for playing the wolf boy teenage heartthrob Jacob Black in the film adaptation of The Twilight Saga. They met backstage in Swift’s dressing room while working in the 2010 rom-com Valentine’s Day. Swift might’ve done the dumping this time around! According to Swiftie lore, the lyrics to her 2010 album Speak Now contains something brand new – an apology!

She later elaborated, saying of the song “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.”

John Mayer (December 2009-February 2010)

Taylor Lautner
Dimitrios Kambouris, Getty Images

John Mayer is a musician known for being a ladies man and making an unfortunate reference to David Duke’s anatomy. Taylor met him during the summer when just 19. Despite never actually confirming that they were a couple, the superstar singers performed together a handful of times, released a duet together and then when all went sour, the break-up songs began!

Mayer’s worldly ways with womanizing seem to have inspired more than one song. In Taylor’s very obviously titled “Dear John” song, she sang “It was wrong, don”t you think nineteen’s too young to be played by your dark, twisted games when I loved you so” and “Dear John, I see it all now that you’re gone, don’t you think I was too young to be messed with, the girl in the dress cried the whole way home, I should’ve known.”

Cory Monteith (April 2010-May 2010)

Cory Monteith
Rick Diamond, WireImage

Cory was a Canadian actor probably best known for his work in Glee, who unfortunately overdosed at age 31. Neither Swift nor the late “Glee” star Cory Monteith ever confirmed that they dated. However, when teased by Ellen Degeneres over all the romances during a show appearance, Taylor turned bright red when Cory’s picture, along with others, were flashed on the screen. Ellen was only trying to figure out which songs were about which guy on Taylor’s album “Red”!

“Stop it, stop it, stop!” Taylor squealed, unwilling to play Ellen”s game of “ringing a bell” to narrow down who the songs on her new album Red are written about. “This makes me feel so bad about myself.”

Jake Gyllenhaal (October 2010-January 2011)

Jake Gyllenhaal
Swarbrick, INFphoto

Jake is a famously private actor who has been super irritated by interviewers asking about Swift while promoting various acting endeavors.

It is said that her song, “All Too Well” is based on her relationship with Gyllenhaal. Back in 2012, Swift told Good Morning America it was one of the more challenging songs to write on her Red album, “All Too Well” was the hardest to write because it took me a long time to filter through everything I wanted to say. It started out being a 10-minute song, which you can’t put on an album. I had to filter it down to a story that could work in the form of a song.” This was two years after the fact! Jake really made a lasting impression.

Eventually, he learned to joke about their past relationship. From one interview during his promotion of the film “Stronger”, detailed on People.com,

“If you lost your legs in real life, do you think Taylor Swift would write a song about it?” Bauman asked Gyllenhaal. “Like a country song?”
“For me, or about it?” Gyllenhaal asked.
“For you,” Bauman said. “Like a country song.”
“She sort of moved more into pop now,” Gyllenhaal responded.

Eddie Redmayne (October 2011-January 2012)

Eddie Redmayne
Getty Images

Onto the British then! Redmayne is an English actor. The two met when Swift auditioned for Les Misérables. They never confirmed having dated and in 2012, Eddie had the following to say, “I absolutely can put the rumors to rest,” Redmayne told Andy Cohen on “Watch What Happened Live”. He was asked about his possible romance with Swift (because if you’re ever linked to Taylor Swift, you will be asked about it, even four years later). “I never went out on a date with Taylor Swift, although I met Taylor Swift. She auditioned for Les Misérables, and she was amazing in the audition.”

Zac Efron (February 2012-March 2012)

Zac Efron
Getty Images

Zac is a well-known heartthrob who met Taylor when they promoted their movie “The Lorax”, for which they’d both contributed character voice-overs while working on separate coasts. They appeared on Ellen together on the promotional rounds and addressed the rumors.

“We are not a couple,” Taylor, 22, said of Zac, 24. “He’s awesome, we are not a couple though,” the singer continued. “You hear people get together when they’re shooting movies, co-stars. But not like animated co-stars. You know what I’m saying.”

Conor Kennedy (July 2012-October 2012)

Conor Kennedy
Paul Adao, INFphoto

Taylor”s summer romance with a member of the American version of royalty lasted a few months. She was 22 and he was 18, and apparently she “freaked him out” by coming on too strong, was the rumor at the time.

“Conor’s just an 18-year-old kid and wasn’t ready for anything super serious,” a pal told RadarOnline.com. “Taylor is looking for her soulmate and it kind of freaked him out with how strong she came on,” the insider went on. The friend also said that Taylor was obsessed with the Kennedy family and was living out a fairytale with Conor. “She was more obsessed with the idea of dating a Kennedy than the actual Kennedy she was dating,” the pal added.

Harry Styles (December 2012-January 2013)

Harry Styles
Tom Meinelt, Splash News

Back to the Brits then! Styles is an English singer, songwriter, and actor, who rose to prominence as a member of the boy band One Direction. His very short relationship with Taylor was heavily scrutinized by the media from the moment they stepped out in public together. Reportedly, Swift wrote “I Knew You Were Trouble” on the album Red about Harry. And then in her album released two years later, “1989”, many decided the song “Out of the Woods” was about Styles as it contained references to their December romance and a snowmobile accident.

Calvin Harris (February 2015-June 2016)

Calvin Harris
Kevin Winter, Getty Images

Calvin is a Scottish DJ, record producer, and singer/songwriter. The two met via an introduction by mutual friend Ellie Goulding, at an English music awards show. He also attended one of Taylor’s famous, heavily Instagrammed “Taymerica” Fourth of July bashes! Calvin and Taylor were loved up for nearly fifteen months and reportedly becoming one another’s muses. There were even rumors of their moving in together. But then…

The two collaborated on a song. Taylor wrote “This Is What You Came For” for Harris under the pseudonym Nils Sjoberg. They’d agreed to keep her part a secret so as not to overshadow him. He released the song with Rihanna on vocals and it became an instant hit. But there was obviously some resentment because the next boyfriend was to have the biggest publicity “roll out” in Swift’s romantic history.

Tom Hiddleston (June 2016-September 2016)

Tom Hiddleston

Just days before her very public breakup with Calvin, Swift was seen awkward-dancing with actor Tom Hiddleston at The Met Gala in May of 2016. Then, a few days post-Harris breakup, Swift and Tom are seen sitting on the beach kissing and cuddling.

Hiddleston’s career took a big hit after the splash of his thirsty looking, heavily Instagrammed romance with Taylor. He was the next boyfriend showcased during her famous Fourth of July bashes and was later widely ridiculed for sporting a handmade, “I <3 T.S.” tank top in her Instagram. However, Taylor had some great visual inspiration to use! In her video for “Look What You Made Me Do,” a troupe of male dancers wear the now iconic tank.

Joe Alwyn (September 2016-present)

Joe Alwyn
Expos, Backgrid

And the winner is…

Taylor seems to have learned something from her very public, and ridiculed, dalliances with Hiddleston and Harris. For the past two-ish years, Swift and Alwyn have quietly enjoyed their relationship, and he’s rumored to have inspired some of the songs on her most recent album, Reputation.

Taylor seems to have learned by putting so much of her romantic life on display in the past. She’s very low-key with her most recent long term relationship and is more likely to urge her fans to vote than she is to Instagram a date.


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