Taylor Swift Boyfriends & Break-ups That Have Inspired Some Major Hits in Her Career

Taylor Swift has built quite the reputation (no pun intended!) as the date-then-write-a-song-about-them type. Besides being an unfair characterization, it is worth mentioning that her relationships have yielded some of the best songs in recent memory.

While her relationships could never last, her songs have left an everlasting impression on fans. In honor of the misunderstood songwriting genius that is Taylor Swift, we take a look at Taylor's dating history and the people behind some of her best songs.

Relationship With Joe Jonas

Taylor's relationship with her boyfriend Joe Jonas, of 'The Jonas Brothers' fame, would be her first high-profile relationship, but not her last. She dated Joe briefly from July 2008 to October 2008 that ended when Joe broke up with her over the phone. 

The suddenness of their breakup inspired Taylor to write the songs 'Last Kiss', 'Forever and Always', and 'Holy Ground'.

Lucas Till

Taylor and Lucas met on-set of the music video for Taylor's song 'You Belong With Me'. They dated for a month in March 2009 and broke up in April. When asked about their month-long relationship, Lucas had this to say:

"We dated for a little bit. But, there was no friction because we were too nice. 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

The two Taylors met on-set of the 2010 movie Valentine's Day. Both were taken with each other and began dating soon thereafter. Their relationship could not last beyond their attraction towards each other. 

Taylor Swift wrote the song 'Back to December' about Lautner, shouldering the full responsibility for their breakup.

John Mayer

There were obvious signs from the very beginning that their relationship could not last. Their more than 12-year age difference and Mayer's notoriety as a playboy should have been reason enough for Taylor to steer clear, but such is the nature of attraction.

The two dated through December 2009 to February 2010. Their messy breakup inspired Taylor to pen the song 'Dear John'. This prompted John Mayer to retaliate with the song 'Paper Dolls'.

Jake Gyllenhaal 

Speaking of age differences, Taylor had a short-lived romance with the actor Jake Gyllenhaal from October 2010 to January 2011. Despite the 8-year age difference, the two clicked and their relationship progressed to the meeting-the-parents phase.

However, their relationship ended as suddenly as it started, and Jake was believed to be the instigator. Reports suggest that several songs on Taylor's album Red were written about Jake including the songs 'All Too Well'.

Connor Kennedy

Taylor's relationship with Robert F. Kennedy's grandson, Connor was doomed from the start. Their relationship started in July 2012; Taylor was 21 then, dating the-then 18-year-old Connor.

Connor's family did not approve of Taylor, and they broke up in October 2012.

Harry Styles

In one of the most publicized flings of the 21st century, Taylor made headlines as the new flame of Harry Styles, of former One Direction fame. 

The two started dating in November 2012, which progressed to exchanging gifts, long trips together, and public displays of affection. They broke up in January the next year after mere months together.

It is believed that Taylor's songs ''I Knew You Were Trouble', 'Out Of The Woods', and 'Style'  were written about Harry.

Calvin Harris

Taylor was acquainted with Calvin Harris via mutual friends on the red carpet of the 2015 Elle Style Awards. The two struck up a romance soon thereafter and made numerous public appearances as a couple. 

After more than a year together, Calvin broke things up, reportedly over rumors of Taylor cheating on him. He is believed to have inspired Taylor's song ''We Are Never Ever Ever Getting Back Together'.

Tom Hiddleston

In keeping with the theme of Taylor dating older men, her romance with actor Tom Hiddleston caused a stir in the media. The two were not coy about their affections and were seen together publicly.

Having been acquainted at the 2016 Met Gala, they stayed together until September that year. 

Joe Alwyn 

Presently, Taylor Swift is enjoying her time together with English actor Joe Alwyn. 

She chooses to keep her relationship with Joe private, for fear of the outside world playing a part in breaking them up. 

They met in May 2017, and have been together ever since.