12 Taylor Swift Heartbreaks And The Songs She Wrote About Them (2023)

Oh the boy who started it all! Alford was Taylor's high school sweetheart and reportedly left her for a good friend of his. This photo was taken for high school prom just after Swift hooked up with this girl. Taylor Swift wrote one of her angriest songs for Jordan. He was the same year as Taylor at Hendersonville High School in Tennessee and they were together before he fell in love with his classmate Chelsea.

Picture to Burn was written about Jordan Alford, whom she called a redneck and says he never let her drive his truck. Here's the heartthrob with the girl he left Taylor for: It's all good, the ending is okay because T-Swift became famous for their songs about rocky relationships and Alford ended up marrying the girl he left Swift for had.

Brandon Borello was Taylor's boyfriend when they were in high school. Their relationship ended because he was a little older than her and had to go to college, but her song about him became the hit on her debut album, which catapulted her to stardom (and luckily still landed her a prom date). , also after Jordan Alford). left her and took someone else).

Tim McGraw's song (and the other positive songs on the album) was inspired by her ex-boyfriend named Brandon Borello as a gift to remind him of her. Taylor told USA Today: "He bought the album and said he really loves it, which is cute. However, his current girlfriend isn't very happy about it." It was named after the musician whose songs he liked. He went to college, so he wanted to write her something to remember her.

Another hit on her first album was written about a guy she liked who she had never really dated. He was surprised when he heard his name in the song. "I never knew he liked me," she said.

"Drew was a real person!" She says. Taylor stated that two years after the song came out, Drew showed up at her house and asked her out. She declined. "It was the perfect ending to a fairy tale, but a little too late."

Sam Armstrong dated Taylor in high school until he cheated on her with another girl. Of course, she wrote the ultimate cheating anthem about their relationship.

I should have said no

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I should have said it wasn't about Sam. proof? In the CD booklet, all S, A, and M were capitalized when in the correct order. It seems that's also when he started developing the serious sass we love his songs for.

Joe Jonas: July 2008 – October 2008

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Fuente
Taylor's first A-list boyfriend was Joe Jonas. Back then, they were both stars in the making when they started dating. However, Joe ended the relationship during a 27-second phone call. We assume that something must have gone terribly wrong. This is something that has been complained about on The Ellen DeGeneres Show and elsewhere. She got her record company to record a song about it, adding it to her album at the last minute.

Forever and Forever, Last Kiss, Holy Land und Better Than Revenge

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The song is called Forever & Always. She also wrote Last Kiss about him: the song not only fits the timeline (when it was written or when they started dating) but also reflects the shock that comes when someone moves on and seemingly forgets you out of the blue. Which definitely happened between them.
Better Than Revenge is about his ex-girlfriend Camila Belle. Thankfully, his latest perspective on Jonas Brother, Holy Ground, is a lot more positive. Released in 2012, Holy Ground takes a positive look back at a past relationship, and aside from the whole Camilla Belle thing, the two seemed to have some pretty good dynamics. He seems to be over Jonas, remembering all the things he loved about dating his fellow pop star.

Taylor Lautner: August 2009 – December 2009

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Taylor Lautner became her boyfriend after they met in her dressing room on the set of the movie Valentine's Day. Their relationship was popularly known as the Taylor Squared. They broke up in late 2009 or early 2010. She mentioned that during her October 29, 2009 appearance on The Ellen Show, she went to a hockey game with him. According to MTV, he was more interested in her than she was in him, he went everywhere to see her, but it didn't work out. They've apparently decided to just be friends.
The romance is rumored to have ended because Taylor (Launter) seemed more interested in adventure than Taylor (Swift).

Back to December

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The song Back to December is probably about Taylor Lautner. The song is an apology for him. At the end of the song, she apologizes to him and makes it clear that she wants to be with him again. The pair never got back together, and at the recent American Music Awards, Swift performed the song, adding "and said...it's too late to apologize" at the end of the band's popular song "Apologize." She alludes to the parody video Taylor Lautner made for "Apologize." Time Magazine mentioned this as one of the top apologies of 2010.

John Mayer: November 2009 – February 2010

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According to his music, Taylor's relationship with fellow musician John Mayer was one of its most tumultuous. She was just 19 when she started dating the notoriously brooding singer. She dated him shortly after collaborating on a song.

Dear John

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"Dear John" is clearly addressed to John Mayer. She boldly captioned Mr. Mayer's first name, splashing lines like, "Don't you think I was too young to mess up? The girl in the dress cried all the way home. I should have known.” Boy, that's hard.

Adam Young aus Owl City: 2010

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Granted, the pair never dated, BUT T-Swizzle met the leader of Owl City and later reportedly sent an email apologizing for his shy behavior and saying he was so amazed to meet her.

Charmed

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"Enchanted" is all about a chance meeting, with Swift even using the word "wonderstruck" (and obviously loving it enough to include her signature scent, too). Young was flattered by the song (who wouldn't be?), so he recorded his own version with a few tweaks to send a message to Taylor. This is so cute, maybe the two should have dated!

Jake Gyllenhaal: October 2010 – January 2011

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Jake Gyllenhaal reported spending $160,000 to ride a private plane on a date. He later broke up with her via text message.

We'll Never Get Back Together, State of Grace, Too Good, Last Time und The Moment I Knew

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Gyllenhaal inspired many of Swift's heartbreaking hits, and for that we thank you, Jake. T-Swizzle admitted The Last Time was about an "unreliable guy" and that Jake's dating history is numbered the same as Taylor's. Around the time the two were one, Gyllenhaal was also linked to Rachel Bilson and Anna Kendrick, so we're sure the "put my name at the top of your list" line was definitely aimed at him. He reportedly spent Thanksgiving with the actor and his family in New York. Later, when "All Too Well" came out, certain lyrics like "Autumn leaves are falling..." and "Your mother tells stories..." allude to this experience. Oh, and "I left my scarf at your sister's house." Case closed.

Conor Kennedy: July 2012 – October 2012

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They broke up due to long distance calls.
When Taylor and Conor, Robert Kennedy's grandson, started dating, Conor was just 18 and going to college at the end of the summer. Reportedly, Taylor took the relationship far more seriously than the teenage golden boy, and even bought a home near him to be closer. The relationship ended after almost three months. Then he sold the house.

start again

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Taylor explained that her single "Begin Again" is about "when you get out of a really bad relationship and finally dust yourself off." Coincidentally, the then 22-year-old had a crush on 18-year-old Conor Kennedy.

Harry Styles: December 2012 – January 2013

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The couple attributed their breakup to the intense media attention and scrutiny their relationship has faced. Another rumor has it that they broke up after a heated argument between them. Swift took a fairly long hiatus from dating after her split from the star, but not before hearing several catchy songs about him.

I knew you were trouble when you came in, out of the woods, style

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It's not surprising to learn that Style is all about Harry Styles. Out of the Woods is also reportedly about ex-boyfriend Harry Styles and has to do with a snowmobile incident the two encountered together. In turn, One Direction's song Perfect is rumored to be inspired by Style's romance with Swift. "I knew you were in trouble when you walked in" is out of the question as T-Swift came out and admitted the song was about his ex-girlfriend from One Direction. She even performed the song to Styles at the Grammys, to which she said, "Well, it's not hard to access that emotion when the person the song is aimed at is standing on the edge of the stage and watching." He He even poked fun at a British accent on stage during his performance. Oh.

Calvin Harris: March 2015 to June 2016

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