Okay so here’s a little info about Taylor’s first boyfriend, Drew Dunlap.
Her first boyfriend Drew Dunlap who broke up with her to go away to college. ‘Tim McGraw’ was written in May 2005. Taylor has admitted to her first kiss being with a guy named Drew, and said her first boyfriends’ name was Drew. As far as I know they went to prom together while Taylor was in 9th Grade (Not the pictures online.) Drew also gave Taylor a Necklace which is found in some of the old pictures in her room. (Pictures above). He’s the right age, lives in Nashville, did go to college, and is friends with some of her old friends and boyfriends and he looks like the guy from the music video (pictures are above) like she says. Plus, she’s said our song was written about the same guy. I have no idea where Brandon Borello comes from because she’s never mentioned the name or anything. Our song again another song about Drew, and Taylor said at VH1’s storytellers his name was Drew, She has said in the past it was about her boyfriend and is the same guy from Tim McGraw. I also think ‘Perfectly Good Heart’ may be about him, although this song is not spoken about much, the song talks about Taylor getting her heart broken, and due to the fact it was written in 2005 it seems to have made sense that it is about him.
(Pictures first and second are Drew Dunlap and his girlfriend Hanna Ward- who I believe was the one who wasn’t impressed about Taylor writing Tim McGraw about him, but don’t hold me to that as I haven’t found a picture of them together before 2010.) (The Third and Forth are the ones in Taylor’s room, with the Necklace which reads Drew)(The Fifth and Sixth are Drew and his parents (Jim and Marilyn))(Seventh picture is Clayton Collins who is in the Tim McGraw video; He looks like Drew, and Taylor said Clayton Collins looked like the guy he was playing)(The last is Taylor and Drew’s parents, so they do know each other and I’m 100% sure that Drew is the Guy ‘Tim McGraw’ & ‘Our Song’ are about, maybe ‘A Perfectly Good Heart’ and the reference with the first kiss in ‘Fifteen’, hence the song is also about him.)
I agree with this post. Therefore here’s more info on drew that I don’t have to post :)