“Teardrops On My Guitar” by Taylor Swift

This track mainly speaks about the frustration and disappointment the singer feels due to her unrequited love for a guy she calls “Drew”. Interestingly, it appears that she and Drew are very close friends, often seeing and talking to each other in school. This is probably the reason she easily falls for him.

However, she is unable to confess her feelings throughout this period, as is obvious in the fact that Drew keeps discussing his relationship with his girlfriend with Taylor. She gets stuck in pretense mood, always trying to seem happy so that he never figures her true emotions out.

Surely this is a complex situation the artist finds herself because this Drew goes to the extent of asking for Taylor’s advice whenever he wants to do something special for his girlfriend. Being the good friend she is, the singer gives him perfect ideas based on what she would love if she was his girlfriend. This makes her even more jealous of this girl because suddenly, she’s getting all the things Taylor wants.

As you would find in the subsequent verses of the song, Taylor, instead of gathering courage and confessing to Drew, continues to hide and is unable to get over him no matter how much she tries. She uses the phrase “Teardrops on my Guitar” to signify the period she was in at the time. Apparently, the song was written during her rise to stardom, as singer-songwriter and guitarist. Unable to change the situation, she ends up mostly crying herself to sleep and sadly concluding that they could be nothing more than mere friends.

Taylor Swift sheds light on “Teardrops On My Guitar”

Taylor once disclosed during a stage performance that the song was really about her schoolmate, particularly, Andrew Hardwick whom she had feelings for. She explained that although all she really wanted was to date Drew, he already had a girlfriend and only considered her as his good friend. The sad aspect of the story was that Drew always confided in her for ideas on the gifts he wanted to give his girlfriend, thus Taylor ended up letting this girl enjoy all the things she wanted including the guy she loved.

Facts about “Teardrops on My Guitar”

Taylor Swift co-wrote this song along with Liz Rose. And it was produced by Nathan Chapman.

Swift was inspired to write “Teardrops on My Guitar” based on a platonic relationship she had in high school with an individual named Drew Hardwick. And a couple of years after the song blew up, he did show up at her house apparently trying to kick it. But by that time Tay Tay had already moved on with her life.

This track came out, via Big Machine Records, on 19 February 2007. It was the second single from Swift’s very first album which was named after the songstress. And it is acknowledged as being her breakthrough song.

The music video to this track, which was nominated for a MTV VMA in 2008, had Trey Fanjoy as its director. And in the video, the role of “Drew” was portrayed by an actor named Chris Keller.

The song itself took home a BMI Country Award (Song of the Year) in 2008 and a BMI Pop Award in 2009.

“Teardrops on My Guitar” reached a peak of number 13 on the Billboard Hot 100. And it also appeared on the UK Singles Chart as well as five different charts in Canada.

This song has also been certified triple-Platinum in the United States.

Did Andrew Hardwick really try to initiate a romantic relationship with Taylor Swift after the release of this song?

Yes. Taylor herself revealed this to HMV magazine. According to her, Drew showed up about 2 years following the release of her album after a breakup, but she told him it was too late. Shockingly, he was arrested together with his wife in 2015 for child abuse.