Fans probably know where Taylor Swift gets her inspiration for writing her music—her former boyfriends.
She has used her heartbreaks to write the most related, not to mention most famous, breakup songs. Who doesn’t know We are Never Ever Getting Back Together or Forever & Always? A lot of Swifties sure do! In fact, even if you’re not a fan, these songs have surely made it to your brain at one point or another.
Because of the intriguing lyrics, however, fans can’t help but dig into the backstory behind Taylor’s every song.
Do you want to know which of Tay-Tay’s hit songs were inspired by someone she’s been romantically involved with? Check out the roundup below to see who among her ex-boyfriends should receive credit for her mega-hit songs.
Jake Gyllenhaal
In case you didn’t know, Taylor and Jake Gyllenhall used to be a thing. They dated in 2010, and she wrote two songs about him — the famous We Are Never Ever Getting Back Together and All Too Well.
What’s the story behind the first song? The Grammy-award winner described the actor as having “exhausting changes of heart” and “pretentious musical tastes.” You could feel Taylor’s emotion about this in the lyrics where she said he could hide away and find his peace of mind “with some indie record that was cooler” than hers.
The second song was about the black striped scarf she wore when she was seen taking a wintery stroll with Jake. This one was quite emotional to a certain degree. She expressed in the lyrics of the song that she had left her scarf at her sister’s house, and that he still has it in his drawer until now.
Taylor told Good Morning America that All Too Well was the hardest song she wrote, and one can see why.
Harry Styles
The 2014 song Style is pretty telling. It’s about her romance with One Direction member Harry Styles. Rumors had it that these two swapped airplane necklaces, which she used for the song’s music video.
Taylor described him in the lyrics, saying he’s got long hair, a slick back, and wears a white shirt, while she was the good girl in a tight little skirt.
From the same album, 1989, the pop giant also dedicated the song Out of the Woods to Harry. There was another reference to the aforementioned airplane jewelry.
In the music video, Taylor donned a princess-like blue dress, which she reportedly wore after their break-up.
The lyrics can be read as trying to make Harry remember when he hit the brakes too soon, resulting in 20 stitches inside a hospital room.
Clearly, Taylor didn’t mind making some investments in writing post-breakup songs about Harry, because she released yet another one, I Knew You Were Trouble.
It referenced the first time they met, and the song was written during one of their many break-ups. The lyrics spoke about Swift learning about Harry moving on from whispers on the street, and they mention that she would be just another notch on his belt.
Joe Jonas
Taylor also wrote songs about her split with Joe Jonas, like in Better than Revenge, but it seemed more about Camilla Belle, who he dated after their separation.
The lyrics were quite controversial for their shaming of someone else. The object of Swift’s spite was cast as evil in some way, and not the woman he (Jonas?) thought. She was, so the song goes, an actress who was better known for the things she did on the mattress.
About the issue, Taylor said she was only 18 when she wrote the song—the time when a woman was afraid someone would take her boyfriend away from her.
Another song about her breakup with Joe was Forever & Always, where she mocked the Jonas Brother member for parting ways with her in a 27-second phone call.
In the lyrics, she asked if she was out of line or said something too honest that made him run and hide like a scared little boy.
Conor Kennedy
Another influential personality on Taylor’s long list of ex-boyfriends is Conor Kennedy. Yup, he is the grandson of the famous politician, lawyer, and US Senator Robert F. Kennedy. The two dated in 2012, and their five years age difference raised some eyebrows.
She dedicated Begin Again to Conor, which was about moving on after a horrible breakup. However, compared to her other break-up songs, this one seemed to put her ex-lover in a good light.
Taylor seemed to like it when he threw his head back, laughing like a little kid but thought it was strange that he found her funny because someone never did.
Was it Jake?
Drew Hardwick
Lastly, one of Taylor’s most famous breakup songs was Teardrops on My Guitar, and if you wondered who among his famous ex-boyfriends it was all about, it was her high school crush, Drew Hardwick, who wasn’t exactly famous until the song came out.
Though he wasn’t actually her ex, it was a classic story of Taylor taking her vengeance. Why?
Did you know that Drew showed up at her home two years after she wrote the song? Despite the degree of her crush on him, she simply said, “Wow, you’re late.”
In the song, Taylor described Drew as someone who could make her laugh, and that she couldn’t see anyone when she was with him.