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Top 10 Taylor Swift Boyfriend Songs

Taylor Swift
Rick Diamond, Getty Images

Taylor Swift has written a lot of songs about her boyfriends, now ex-boyfriends. Like, a lot of songs. While she's well known for the ones written as sweet revenge on a guy who broke her heart, there are a number of love songs penned during or after her relationships with these men, both famous and not.

Taylor Lautner, Joe Jonas and John Mayer are a few of Swift's former celebrity romances, but there's also Drew, Sam, and the boyfriend who inspired her very first hit, 'Tim McGraw.' Yes, he was real, and his relationship with the songwriter ranks high on this list of the Top 10 Taylor Swift Boyfriend Songs. Scroll through the list and decide which is your favorite. If there is one we left out that you feel should have been included, tell us why in the comments section below. 


Fearless
10

'Forever and Always'

From 'Fearless' (2008)
 
 

'Forever and Always,' about Joe Jonas, was written just before copies of Swift's 2008 'Fearless' album were pressed. The pop boyband member famously dumped Swift in a phone call that lasted just 27 seconds. Hey, it could've been worse -- he could have just texted! While the song was never released as a single, it marks the first time the singer called out a famous ex-boyfriend on an album.

 
We Are Never Ever Getting Back Together
9

'We Are Never Ever Getting Back Together'

From 'Red' (2012)
 
 

Swift's lead single from her 'Red' album (2012), 'We Are Never Ever Getting Back Together,' is about an ex-boyfriend who keeps trying to weasel his way into her arms. The singer slams the door on the lover, but hasn't yet addressed who the song is about. Our best guess is the boyfriend song is about actor Jake Gyllenhaal, or perhaps a lover she carried on away from the glare of media in the spring of 2011.

 
Speak Now
8

'Dear John'

From 'Speak Now' (2010)
 
 

This may be the most biting Taylor Swift song about a past boyfriend, as she practically throws the curtain up on all the sexy details of her romance with the famous serial lover. 'Dear John' is about John Mayer, and unveils how he treated her during their short relationship. Mayer said the song "humiliated" him, and he believes he didn't deserve that sort of treatment. We're not convinced.

 
Picture to Burn
7

'Picture to Burn'

From 'Taylor Swift' (2006)
 
 

'Picture to Burn' counts as a boyfriend song even though the singer says she and the "redneck" that wouldn't let her drive his truck didn't officially date. We're not going to get caught up on the semantics. "We almost dated," Swift admits. "It really bothered me that he was so cocky and that's where that song came from." It's this song that showed fans that Swift is able -- and willing -- to write a sharp response to a boyfriend who treats her poorly.

 
Speak Now
6

'The Story of Us'

From 'Speak Now' (2010)
 
 

This song from 'Speak Now' is also about John Mayer, as Chris Willman of Yahoo clearly pointed out in May of 2011. The secret message in the lyric book was C-M-T-A-W-A-R-D-S, and Swift admitted it was the last song added to the album. Mayer appeared at the CMT Awards the previous year, playing with Keith Urban. Earlier, Swift talked about how the song was inspired by an awkward moment at an awards show, and then she told USA Today that 'Dear John' and 'The Story of Us' were about the same person.

 
Should've Said No
5

'Should've Said No'

From 'Taylor Swift' (2006)
 
 

Taylor Swift wrote 'Should've Said No' about her high school boyfriend named Sam, whom she learned was cheating on her. This song from her self-titled debut album was her second No. 1 hit and an early example of Swift's ability to get back at a boyfriend with her guitar and pen.

 
Our Song
4

'Our Song'

From 'Taylor Swift' (2006)
 
 

Not all of Taylor Swift's best boyfriend songs end with the singer broken-hearted. Swift never names the boy who inspired 'Our Song,' so we can only assume he was one of her early pre-fame loves. "I wrote it about this guy I was dating," she says, "and how we didn't have a song. So I went ahead and wrote us one. I think there's just some sort of magic in the way the track sounds like it's bouncing, almost!"

 
Back to December
3

'Back to December'

From 'Speak Now' (2010)
 
 

Swift wrote 'Back to December' about actor Taylor Lautner, her boyfriend during the fall of 2009. It's the one song on this list of Taylor Swift boyfriend songs that finds the singer apologizing to a guy she did wrong, instead of the other way around. The male Taylor was a good catch, it seems, and by the time she cut 'Speak Now,' Swift was regretful.

 
Tim McGraw
Ethan Miller, Getty Images
2

'Tim McGraw'

From 'Taylor Swift' (2006)
 
 

Some argue Taylor Swift's first hit is about a boyfriend named Brandon, while others say it was about Drew, the guy who inspired 'You Belong With Me.' Taylor and Drew never really dated, so we'll settle on Brandon as the subject of this nostalgic love song. The boy in question went off to college and the relationship ended. On the plus side, country music got a new superstar out of the breakup.

 
Ours
1

'Ours'

From 'Speak Now' (2010)
 
 

For some reason, there isn't the same interest in the happy Taylor Swift boyfriend songs as there are the ones that end in heartbreak or revenge. This hit from 'Speak Now' is arguably the singer's sweetest love song to date -- just try not smiling when you hear it! So who is Taylor Swift's 'Ours' about? We think it's another about John Mayer, written before they broke up. However, that would mean there are three songs on the album about Mayer. Did he hurt her that badly?

 

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