Taylor Swift Breakup Songs: Who Has She Targeted?

by at .

Taylor Swift has this thing, don't know if you knew about it, where she dates these famous men, and then after they break up, she writes these scandalous songs about them.

She even leaves little clues about the subjects of her songs in the liner notes of her albums, so not only does she trash these guys, she also makes it into a game we can all play together!

Many of her songs are about celebrities, guys like Jake Gyllenhaal, Harry Styles, and John Mayer.

But which song matches which ex?!

Read on to find out!

1. "Should've Said No"

"Should've Said No"
This song was on Taylor's self-titled debut, back when she was dating fellow high school students instead of celebrities. It was written about her then-boyfriend, Sam Armstrong, who cheated on her.

2. "Picture to Burn"

"Picture to Burn"
This is about another high school boyfriend, Jordan Alford, who reportedly dumped Taylor for one of her best friends. Bad move, Jordan.

3. "Our Song"

"Our Song"
This is one of Taylor's few happy love songs, and it's about yet another high school boyfriend, Brandon Borello. Legend has it that she first performed this song at her school's talent show.

4. "Tim McGraw"

"Tim McGraw"
This is another song about Brandon Borello, and it's pretty bittersweet. Taylor and Brandon ended up breaking up after he went off to college, so when she sings lines like "He said the way my blue eyes shined ' Put those Georgia stars to shame that night / I said, 'That's a lie,'" you know she means it.

5. "Teardrops on My Guitar"

"Teardrops on My Guitar"
This tragic little ditty is about Drew Hardwick, a guy from high school who Taylor never dated but was super into. She was so into him that she even put his name directly into this song. Four times.

6. "Fifteen"

"Fifteen"
This is from Taylor's second album, Fearless, but you'll never believe who it's about -- yep, good ol' Brandon Borello. What a heartbreaker he was, huh?

7. "Hey Stephen"

"Hey Stephen"
Here's another song where Taylor was kind enough to put the dude's name right in there. The Stephen in this song is Stephen Barker Liles, a member of the country duo Love and Theft. Taylor toured with Stephen in 2008, and she was apparently feeling him. Obviously though, things did not work out.

8. "Forever & Always"

"Forever & Always"
Here we go, friends, we're finally starting to get to the good stuff. This song right here is about Joe Jonas, who broke Taylor's heart when he broke up with her in a text message. Her first tabloid romance, how sweet!

9. "Better Than Revenge"

"Better Than Revenge"
This is from Taylor's third album, Speak Now, and it, too, is about Joe Jonas. More specifically, it's about how Joe moved on with actress Camilla Belle after he broke up with her. And it is downright nasty.

10. "Dear John"

"Dear John"
Taylor must have had a lot of time for meaningful romance between this album and her last one, because this is another intense song. It's about -- who else? -- John Mayer and his sleazy, sleazy ways.

11. "Back to December"

"Back to December"
Here's a very sweet, sad little song about Taylor Lautner, and there's a fun little twist to it, too, because in this song, ol' Swifty is the bad guy. The whole thing is about how she regrets how she treated him. Poor Taylor(s).

12. "Mine"

"Mine"
This one's kind of weird: rumor has it that "Mine" is about Cory Monteith. They never admitted they dated, and if they did, then they weren't together for long, but still, it's a sweet little song.

13. "The Story of Us"

"The Story of Us"
Well, lookie here, another song about John Mayer! Where "Dear John" was angry, "The Story of Us" is more melancholy. It's Taylor thinking about what might have been. How ridiculous, right, thinking of having a happy ending with John Mayer?

14. "Holy Ground"

"Holy Ground"
This is from Taylor's fourth album, Red, and it's about Joe Jonas. What a throwback, right? But with this song, it sounds like Taylor finally forgave Joe. "Tonight I’m gonna dance for all that we’ve been through," she sings, "But I don’t wanna dance if I’m not dancing with you.

15. "We Are Never Ever Getting Back Together"

"We Are Never Ever Getting Back Together"
Ah, and here we have the start of Taylor's Jake Gyllenhaal period. This song is widely said to be about Jake because of its music video, which features an actor that looks a lot like him and which also features scarves. Scarves were big for Swiftenhaal.

16. "All Too Well"

"All Too Well"
You know how we just said scarves were big for Taylor and Jake? That's why people think this song is about him, too: Taylor wrote a lyric that went "I left my scarf there at your sister's house / And you've still got it in your drawer even now." Aww, guys.

17. "I Knew You Were Trouble"

"I Knew You Were Trouble"
Look, look, it's Taylor's first song about Harry Styles! She's even admitted as much -- she did the song at the Grammys and used an embarrassing English accent in the performance. Later, she said "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."

18. "Starlight"

"Starlight"
Remember when Taylor Swift dated her very own Kennedy? It was a beautiful time for us all. She seriously had a relationship with 18-year-old high school student Conor Kennedy, and to commemorate their relationship, she wrote this song from the point of view of his grandmother, Ethel Kennedy. Brilliant.

19. "Style"

"Style"
This song is from Taylor's fifth album, 1989, and it's about Harry Styles. She's hinted that most of the songs on the album are about him, but this is pretty pointed since the title is just basically his last name.

20. "Out of the Woods"

"Out of the Woods"
Here's another song that Taylor has confirmed is about Harry Styles. The lyrics reference a paper airplane necklace of his that she wore during their short relationship, and it also mentions a snowmobile accident they had together. What a roller coaster courtship.

Wait! There's more! Just click "Next" below:

Next
Show Comments
Star:
Taylor Swift
Related Photos:
Taylor Swift Slideshows
Related Post:
Created by:
Published:

Taylor Swift Biography

Taylor Swift and Friend
Taylor Swift is the next big thing in country music. She hails from Pennsylvania and has a younger brother named Austin. Personally,... More »
Born
Full Name
Taylor Swift

Taylor Swift Quotes

I think it's kind of fun to call out your ex-boyfriends. Like why do this if you're not gonna take the opportunity to always have the last word. It's so much fun.

Taylor Swift

I saw that documentary on Britney Spears, and I feel bad for her—she can't leave her house!

Taylor Swift