Taylor 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.

“Teardrops On My Guitar” is certified 3x Platinum by the RIAA.