“Teardrops On My Guitar” illustrates the unrequited love Taylor felt for classmate Drew Hardwick. Taylor told fans that Drew would often ask her for advice and date ideas for
his girlfriend, and she would give him ideas to be a good friend.
Written by Taylor and Liz Rose, this song of unrequited love is based on a true experience during Taylor's schooldays when she had a crush on a boy she was friends with. However there was no
chance of him reciprocating her feelings as he already had a girlfriend whom he was madly in love with and he used to tell Swift all about her. He was completely unaware of Taylor's feelings.
She told fans during an acoustic performance:
"This is a song that I wrote about a guy who went to school with me, and I was that ‘friend,’ you know, that girl who’s your friend. And, you know, he had this awesome girlfriend who he would
tell me about every single day. And, you know, I was that girl that he would go to and be like, ‘what should I get her for Valentine’s Day? I have to make this Valentine’s Day so awesome! It’s
her birthday, what should I do? What would the perfect gift for a girl be?’ And of course I’d give him, like, the most awesome ideas, awesome plans, like, I would want them! And, you
know, it didn’t end up, like, in the end of the chick-flick where they get together in the end. It didn’t happen like that. So I wrote a song and I put it out on the radio, and they’re still
together! […] I think right under his driver’s license where it says ‘Drew Hardwick’ it says ‘Taylor wrote a song about me.’ But I haven’t talked to him in a while, I haven’t talked to him for
probably a year and a half, but I’ve heard through the grape vine that he’s very well aware of [the song.] But, you know, it’s crazy how having a top five hit with a song won’t get you over
somebody." -- Taylor Swift
Years afterwards, Drew appeared at Taylor's house, but she rejected him. She went on to explain what happened:
"About two years after the album came out in the States, he showed up in my driveway. Apparently he and his girlfriend had broken up so that was his first stop when he was back in town. I was
like 'you are so late, y'know. If you'd stopped by right after the album came out then that would be one thing, but…I remember reading on his MySpace page one time 'My name's Drew and I have a
famous song written about me. Email me and I'll give you details.' I was like, right, wow, note taken." -- Taylor Swift
In 2015, Drew and his wife, Joni, were arrested in Hendersonville, Tennessee, on charges of child abuse.
Taylor was 17 when the song was released (it was her second single, following "Tim McGraw"). She became the first teen country star to make a major crossover into the pop charts since LeAnn
Rimes. This seemed like a pretty big deal at the time, but her pop breakout was just one step in Taylor's journey toward becoming one of the biggest stars of the following decade.
Critics received the track generally positively, complimenting Taylor's vocal delivery and songwriting style. The song is considered to be her breakthrough single, as it spread her popularity
throughout the United States. It was commercially successful, peaking at #13 on the Billboard Hot 100, becoming the best-charting single from "Taylor Swift" on the chart, and being
Taylor's debut entry on the Billboard Year-End Hot 100 charts.
Its music video was directed by Trey Fanjoy and features Taylor as she sees her love interest develop a relationship with another female. Two fans who won a contest to spend
the day with Taylor got to see the video on her tour bus before it was released.
"Teardrops On My Guitar" won the prestigious "Song of the Year" award at the 2008 Annual BMI Country Awards. It was honored for receiving more airplay in the past year than any other country