Taylor Swift told Great American Country about this song: "If anyone has heard this song and really listened to it, they realize it's not about Tim McGraw. It's about a relationship that I was in. Just to set the record straight, it wasn't with Tim McGraw. It was with this guy I was dating and he was about to go off to college and I was thinking about all the things that I knew would remind him of me. I didn't really think of Tim McGraw personally when I wrote this song. It was a song where I was listing personal things. One of things that I listed was that my favorite song is by Tim McGraw." Swift added: "The guy I wrote Tim McGraw about, I dated him for about a year and we are still friends, but we don't talk that much because his new girlfriend isn't too much of a fan. He really thought it was cool that, even though we weren't going out anymore, I remembered our relationship nicely. I think that he was happy that I didn't write ' Picture To Burn' about him, another song on my album."
When McGraw was co-hosting CMT's Country Countdown USA show with Lon Helton, he was asked by his co-host what he thought the first time he heard this song. Tim replied, "It was awesome. I didn't know if I should take it as a compliment, or if I should feel old." Helton then asked Taylor Swift the same question The young singer-songwriter responded: "Definitely it was meant as a compliment."
Swift told the story of the song in press materials: "This song means so much to me, that's why we wanted it to be the first track on the album. The idea for this song came to me in math class. I just started singing to myself, 'When you think Tim McGraw.' The concept for this song hit me, because I was dating a guy who moved away, and it was going to be over for us. So I started thinking of things that I knew would remind him of me. The first thing that came to mind was that my favorite song is by Tim McGraw. After school, I went downtown, sat down at the piano, and wrote this with Liz Rose in fifteen minutes. It may be the best fifteen minutes I've ever experienced."
Taylor linked up with Tim McGraw seven years later when she provided harmony vocals for his Two Lanes Of Freedom track, " Highway Don't Care." McGraw told Billboard magazine in an interview plugging his 2013 album that he didn't know Swift when her breakthrough single was released. "The first thing I thought was, 'Have I gotten that old?'" he said with a laugh. "I didn't realize she was like 12 or 13 when she wrote it. It's a great song. Taylor is really special, and she's gotten exponentially better with every project. She owns her style now. Instead of searching for a style or trying to be something, she owns who she is."