Joe Jonas (2008)
Taylor dated the former Jonas Brother from July 2008 to October 2008. This was Taylor’s first public breakup, and possibly most brutal being that Joe decided to do the heartbreaking over a 27-second phone call.
The country crooner’s songs Last Kiss and Forever and Always are believed to have been written about her breakup with Jonas, while Holy Ground is a later, more positive perspective on the short-lived romance. Her more recent release Mr. Perfectly Fine is also believed to be about the split.
Lucas Till (2009)
Taylor and Hollywood heartthrob Lucas Till dated for only a matter of months in 2009, after Lucas played the next-door neighbour in Taylor’s You Belong With Me music video. Lucas later spoke out about the two’s brief attempt at dating, stating that at the end of the day, they were better as friends.
“We dated for a little bit. But, there was no friction because we were too nice,” he told MTV. “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 it’s passionate, and with us, I really just liked her as a friend. That’s the only reason that didn’t work out.”
Taylor Lautner (2009)
Who could forget the Taylor/Taylor romance of 2009? The two met when they co-starred as high school sweethearts in the romantic comedy Valentine’s Day. Taylor’s song Back To December — where she sings: “Your tanned skin, your sweet smile”, on top of an apology for a rough night in December — is about Lautner, and the night she dumped him.
John Mayer (2009)
Taylor’s song Dear John is about – you guessed it – John Mayer, and some of the lyrics are pretty cutting. “Don’t you think I was too young to be messed with? The girl in the dress, cried the whole way home,” she sings, but John reckons the song was out of line.
“It made me feel terrible because I didn’t deserve it,” Mayer told Rolling Stone in a 2012 interview. “I’m pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy thing for her to do.”
Later, Mayer responded musically with his song Paper Dolls on his 2013 album Paradise Valley. “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,” he sings.
Cory Monteith (2010)
Though Taylor and the Glee star never officially confirmed they were dating, the two were photographed together on many occasions. Taylor also clearly blushed when asked if the two had dated on The Ellen DeGeneres Show. On the day of Cory’s tragic death in July 2013, Taylor tweeted: “Speechless. And for the worst reason.”
Jake Gyllenhaal (2010-2011)
One of Taylor’s most public relationships, the couple were regularly seen out in New York City and Los Angeles. Rumour has it the couple’s 10-year age gap just wasn’t working so Jake called it quits. The Last Time — with lyrics “Put my name at the top of your list” — is said to be about this romance.
All Too Well from her album Red, which documents the infamous scarf situation, is also about Gyllenhaal. This song references a number of details specific to their relationship, including a car trip to upstate New York and a Thanksgiving dinner at Maggie Gyllenhaal’s house.
In the first verse, Swift makes this fascinating claim: “Left my scarf there at your sister’s house. And you’ve still got it in your drawer even now” to the dramatic end “Now you mail back my things and I walk home alone, But you keep my old scarf from that very first week ‘Cause it reminds you of innocence and it smells like me.” Gyllenhaal has been photographed in years since wearing Taylor’s scarf, much to the amusement and confusion of Swift fans.
Adam Young (2011)
Owl City’s Adam Young never officially dated Taylor, with things never escalating past some emails and one face-to-face meeting. Taylor was so excited to meet Young that she later wrote the song Enchanted about him.
She sings: “All I can say is it was enchanting to meet you”. Young later released a cover version of Taylor’s song Enchanted on Valentine’s Day when he realised the song was about him.
Chord Overstreet (2011)
Taylor and Chord reportedly only went on one date, but there are pictures from the event so, naturally, he makes the list.
Eddie Redmayne (2011-2012)
It is rumoured that Taylor and Eddie started dating when she auditioned for the part of Eponine in Les Miserables. They were seen together a lot in New York while the auditions were taking place. Unfortunately, Eddie’s captivating green eyes and freckles didn’t make enough of an impact to earn a tribute track.
Zac Efron (2012)
Once Disney’s High School Musical teenage stud, Zac has been making our hearts skip for years prior to his run-in with Tay. The two reportedly started dating for a few months while promoting their movie The Lorax. However, they have both denied the relationship.
The pair even went as far as to write a song together rejecting the dating rumours through a parody of Foster the People’s Pumped Up Kicks on The Ellen DeGeneres Show. We can still dream though.
Conor Kennedy (2012)
Taylor dated Robert F. Kennedy’s grandson Conor Kennedy during the summer of 2012. She did receive some criticism for the age difference in the relationship, being that she was 22 and Conor was 18. Taylor even purchased a home near the Kennedy compound in Hyannis Port, Massachusetts, during the romance. It started to look like things between Taylor and Conor weren’t going so well when his family accused the singer of crashing the wedding of Conor’s cousin Kyle in August. Her reps denied it, but it appeared the damage had been done.
Begin Again has been linked to Conor, especially the lyric: “I think it’s strange that you think I’m funny ’cause he never did.”
Harry Styles (2012-2013)
One of Taylor’s most divisive relationships to date. The couple, despite only dating for a month, shared paper aeroplane necklaces, strolled through Central Park, kissed in Times Square on New Year’s Eve and even got in a snowmobile accident.
I Knew You Were Trouble is about the One Direction heartthrob. Taylor’s album 1989 is also filled with subtle references to Harry, especially Out Of The Woods with its lyrical references to their December romance and the accident, and Style which is fairly self-explanatory.
Calvin Harris (2015-2016)
Taylor and Calvin shared a fairly long romance and was her most well-documented. The couple would regularly appear on red carpets together and post images to their social media pages. Multiple reports claim that it was Calvin who wanted to break up.
While neither have ever commented on it, Taylor’s hit We Are Never Ever Ever Getting Back Together was presumed to be about Calvin. However, many Swift fans remain confident this is about Jake.
Tom Hiddleston (2016)
Tom Hiddleston and Taylor Swift, better known as Hiddleswift, was the love story that shocked the globe. The couple met in New York and then took their romance on the road (Rhode Island, Italy, Australia, and England to name a few stops).
But sadly, all good things must come to an end. Just two months after Tom was photographed in an ‘I Heart T.S.’ t-shirt, the couple would call it quits. It’s believed that Getaway Car was written about Taylor ending her relationship with Calvin to get with Tom.
Joe Alwyn (2017-Now)
Fast forward to now, and Taylor and current beau Joe Alwyn have been happily dating for over four years. The couple has done a very good job of keeping their relationship shrouded in mystery. Taylor and Joe were first photographed in 2017, enjoying a coffee on a balcony in Nashville.
Taylor has written plenty of songs about Joe, including London Boy and Gorgeous from her Loven album, with lyrics: “You make me so happy, it turns back to sad.” She also penned tracks believed to be about their romance for one of her latest albums, Folklore, including songs like Invisible String and Peace.
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