Written by Taylor Swift 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.
In an interview with the HMV magazine, Taylor revealed that this song was written for a boy named Drew, who only ever saw her as a friend, despite Taylor having feelings for him. She went on to explain what happened when he realized the song was about him. Said Taylor: "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."
In an interview with the HMV magazine, Taylor revealed that this song was written for a boy named Drew, who only ever saw her as a friend, despite Taylor having feelings for him. She went on to explain what happened when he realized the song was about him. Said Taylor: "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."
This song had two different chart runs on the Hot 100. It was originally a Country hit and charted on the Hot 100 based on its success in the Country format. As a result of the success of it's follow-up, "Our Song," a remix of "Teardrops on My Guitar" was released to Pop and Adult Contemporary radio. They gave it sufficient airplay to give it a second life on the Hot 100.
Taylor Swift was 17 when this was released. She is the first teen Country star to make a major crossover into the Pop charts since LeAnn Rimes.
Tyler Hilton, who played Chris Keller on the TV show One Tree Hill, plays the boy in this video. Hilton is also a singer/songwriter.
This is available in both Country and Pop mixes. (thanks, Bertrand - Paris, France, for above 3)
This was iTunes #1 selling Country single in 2007.
There are a couple of names of guys in her songs. "Drew," is the name of the guy in this song, and "Cory" is the name of the guy in "Stay Beautiful." Yes, these are names of real people, and they have both tried to contact her since these songs have come out. (thanks, Lance - Carroll, IA)
This song 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 song.
On the Billboard 200 chart dated November 7, 2009, Taylor Swift logged its 157th week on the chart. In doing so it overtook the 156 weeks spent by Nickelback's All the Right Reasons, giving the album the longest stay on the survey by any release in the 21st century.