With Taylor Swift’s breakup with Calvin Harris currently buzzing around the Internet, fans are no doubt expecting some stellar new music to be sparked by the end of the longest relationship the singer has experienced to date. If Taylor’s songwriting past is anything to go by, she’s probably already penning verses to help her through saying goodbye and once again welcoming singledom. While we grieve for the loss of one of our fave celeb couples, take a peek at six Taylor Swift songs and the ex-boyfriends that she was singing about.

1. Joe Jonas (July 2008-October 2008): Taylor Swift and Joe Jonas seemed like the perfect young pop couple, until he apparently broke up with her over the phone in a call that lasted less than 30 seconds. Ick. The breakup was the supposed influence behind Taylor’s songs “Last Kiss” and “Forever and Always,” as well as the hindsight melody “Holy Ground.”

2. Taylor Lautner (August 2009-December 2009): The world swooned over Taylor+Taylor as much as the young duo seemed to swoon over each other when news got out that they were dating. Appearing together in the romantic movie Valentine’s Day, the on-screen couple soon became an off-screen item. When the relationship fizzed out after just a few months, Taylor wrote “Back to December” (the month they broke up), which references a fellow with “tan skin” and a “sweet smile.” Sound familiar?

John Mayer Taylor Swift

3. John Mayer (December 2009-February 2010): Still just 19 when she dated John Mayer, the relationship wasn’t at all smooth sailing, and the breakup was apparently just as brutal. Taylor publicly aired her feelings about how she had been treated in the blatantly named “Dear John” while singing the lines, “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.” Oof.

Taylor Swift Cory Monteith

4. Cory Monteith (April 2010-May 2010): Although Glee’s Cory Monteith and Taylor Swift experienced a brief romance that was never officially confirmed, Taylor did tell Yahoo that two of her songs, “Speak Now” and “Mine” were based on a boy “that I just barely knew put his arm around me by the water, and I saw the entire relationship flash before my eyes.” So sweet!

Jake Gyllenhaal

5. Jake Gyllenhaal (October 2010-January 2011): Taylor Swift admitted to her confidence being easily shaken in an interview with NPR, where she also explained that her song “The Last Time” is about an “experience I had with someone who was kind of this unreliable guy. You never know when he’s going to leave; you never know when he’s going to come back, but he always does come back.” This perfectly describes the few months that Taylor spent with Jake Gyllenhaal, who had plenty of priorities but a stable relationship with Tay not being one of them.

Harry Styles

6. Harry Styles (December 2012-January 2013): The pop music-loving world almost exploded when news got out that Taylor was dating One Direction’s Harry Styles. But the relationship was as short-lived as it was apparently rocky, with “I Knew You Were Trouble” and “Out of the Woods” rumored to be about the 1D singer… and even references to the duo’s snowmobiling accent making their way into her song. Ouch.

Of all these, seems like John Mayer was a learning lesson for young Taylor, while the relationship with Harry Styles might have been one she would have wanted to avoid completely. But it might be this current breakup that will be the hardest to get over. Here’s hoping the songs Calvin inspires have a happier ending!

What’s your fave Taylor Swift breakup song? Tweet us @BritandCo!

(h/t Billboard, photos via @TaylorSwift, Dimitrios Kambouris, Larry Busacca, Eamonn M. McCormack, Mark Davis/Getty)