HomeCelebs12 Taylor Swift Heartbreaks and The Songs She Wrote About Them

12 Taylor Swift Heartbreaks and The Songs She Wrote About Them

Jordan Alford (2003)

Oh, the boy that started it all! Alford was Taylor’s high school boyfriend and he reportedly dumped her for one of her own good friends. This picture was taken for high school prom, not long after Swift got left for this girl. Taylor Swift wrote one of her angriest songs for Jordan. He was in the same year as Taylor at Hendersonville High School in Tennessee and they went out before he romanced fellow classmate Chelsea.

Picture to Burn

Picture to Burn was written about Jordan Alford, whom she called a redneck, and says he never let her drive his pick-up truck. Here’s said heartbreaker with the girl he left Taylor for–all is well that end’s well, because T-Swift became famous for her songs about rocky relationships and Alford ended up marrying the girl he left Swift for.

Brandon Borello (2003)

Brandon Borello was Taylor’s boyfriend while they were in high school. Their relationship ended because he was a bit older than her and had to go to college, but her song about him became the hit on her debut album that catapulted her to stardom (and luckily she still got a date to prom, even after Jordan Alford dumped her and took someone else).

Tim McGraw, Our Song, Fifteen

The song Tim McGraw (and the other positive songs on the album) was inspired by 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 loved it, which is sweet. His current girlfriend isn’t too pleased with it, though.” It was named after the musician whose songs she liked. He was going away to college so she wanted to write him something to remember her by.

Drew (2004)

Another hit song on her first album was written about a boy she liked, whom she never actually dated. He was surprised when he heard his name in the song. “I never knew she liked me,” he said.

Teardrops on My Guitar

“Drew was a real person!” she tells. Taylor stated that two years after the song came out Drew showed up at her house and asked her on a date. She declined. “It was the perfect fairytale ending but a little too late.”

Sam Armstrong: 2004

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

Should’ve Said No

Should’ve Said No was about Sam. Proof? In the CD booklet, every S, A, and M was capitalized if it was in the correct order. It looks like this is also when she began to develop the serious sass that we love her songs for.

Joe Jonas: July 2008 – October 2008

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

Forever and Always, Last Kiss, Holy Ground, & Better Than Revenge

Forever & Always is the name of that song. She also wrote Last Kiss about him–Besides matching up timeline wise (when written versus when they dated), the song is a reflection of the shock felt of having someone move on and seemingly forget about you out of the blue. Which is definitely what happened between them.
Better than Revenge is about his ex-girlfriend, Camila Belle. Luckily, her latest perspective on the Jonas Brother — “Holy Ground” — is a lot more positive. “Holy Ground,” which was released in 2012, looks back positively on a past relationship, and besides the whole Camilla Belle thing, the two seemed to have a really good dynamic. She seems to have gotten over Jonas and is looking back at all the things she loved about dating her fellow pop star.

Taylor Lautner: August 2009 – December 2009

Taylor Lautner became her boyfriend after they met on set for the film Valentine’s Day, in her dressing room. Their relationship was popularly known as Taylor Squared. They broke up in late 2009 or early 2010. She mentioned going to a hockey game with him during her October 29th 2009 appearance on The Ellen Show. According to MTV he was more into her than she was into him, he going everywhere he could to see her, but it was not working out. They have apparently decided to just be friends.
It is rumored that the romance came to an end because Taylor (Launter) seemed to be more into the fling than Taylor (Swift).

Back to December

The song, Back to December is suspected to be about Taylor Lautner. The song is an apology to him. At the end of the song she asks for his forgiveness and hints to the fact she wants to be with him again. The couple hasn’t reunited and at the recent American Music Awards Swift performed the song and at the end added “and he said..it’s too late to ‘pologize” from popular song “Apologize” by the band One Republic. She is alluding to the parody video Taylor Lautner made for “Apologize”. Time magazine listed this is one of the top apologies of 2010.

John Mayer: November 2009 – February 2010

According to her music, Taylor’s relationship with fellow musician John Mayer was one of her most tumultuous. She was only 19 when she dated the notoriously broody singer. She dated him briefly after collaborating on a song.

Dear John

Dear John is clearly directed at John Mayer. Boldly entitling the cut after Mr. Mayer’s first name, she spewed out lines like, “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.” Geez, that’s heavy.

Adam Young of Owl City: 2010

True, the pair never dated, BUT T-Swizzle did meet the Owl City front man, and reportedly he later sent an email apologizing for his shy behavior, saying he was just so wonderstruck to meet her.


“Enchanted” is all about a chance meeting, with Swift even using the word ‘wonderstruck’ (and apparently she loved it enough to name her signature fragrance scent after it as well). Young was flattered by the song (who wouldn’t be?), so he recorded his own cover with a few tweaks to direct a message back at Taylor. This is so sweet — maybe the two should have actually gone out!

Jake Gyllenhaal: October 2010 – January 2011

Jake Gyllenhaal reported spent $160,000 to have her flown over on a private jet for a date. He later broke up with her through text.

We Are Never Ever Getting Back Together, State of Grace, All Too Well, The Last Time, and The Moment I Knew

Gyllenhaal inspired many love and heartbreak hits out of Swift–and for that we thank you, Jake. T-Swizzle admitted that “The Last Time” was about an “unreliable guy,” and Jake’s dating history is just as numbered as Taylor’s. Right around the time the two were a thing, Gyllenhaal was also tied to Rachel Bilson and Anna Kendrick, so we’re sure the line “put my name on top of your list” was most definitely directed towards him. She reportedly spent Thanksgiving with the actor and his family in New York. Later when “All Too Well” came out, certain lyrics like “The autumn leaves falling down…” and “Your mother telling stories…” point to that experience. Oh, and “Left my scarf at your sister’s house.” Case closed.

Conor Kennedy: July 2012 – October 2012

Broke up due to long-distance issues.
When Taylor and Conor, who is the grandson of Robert Kennedy, started dating, Conor was only 18 and leaving for college at the end of the summer. Reportedly, Taylor took the relationship much more seriously than the teenage golden boy, even buying a house near his to be closer. The relationship ended after almost three months. She then sold the house.

Begin Again

Taylor explained that her single “Begin Again” is about, “When you’ve gotten through a really bad relationship and you finally dust yourself off.” Coincidentally, the then 22-year-old was enamored with 18-year-old Conor Kennedy.

Harry Styles: December 2012 – January 2013

The pair credited their breakup to the intense media attention and scrutiny that their relationship was subject to. Another rumor is that they split after a heated argument with each other. After her break up with the star, Swift took a pretty lengthy break from dating–but not before she got several catchy tunes out about him.

I Knew You Were Trouble When You Walked In, Out of the Woods, Style

It’s not surprising to learn that Style is about Harry Styles. Out of the Woods is supposedly about ex-boyfriend Harry Styles as well, and has to do with a snowmobile incident the two encountered together. In turn, the One Direction song Perfect is rumoured to be inspired by Styles’ romance with Swift. “I Knew You Were Trouble When You Walked In” isn’t up for debate, as T-Swift came right out and admitted the tune was about her ex One Direction flame. She even performed the song right in front of Styles at the Grammys, to which she said,”Well, it’s not hard to access that emotion when the person the song is directed at is standing by the side of the stage watching.” She even mocked a British accent onstage during her performance. Ouch.

Calvin Harris: March 2015-June 2016


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