https://raretaylorswift.webs.com/apps/photos/ Boyfriends! Taylor's first boyfriend Drew's 10th grade yearbook picture. He's the guy Tim McGraw and Our song are about. (She's admitted his name was Drew; Brandon doesn't exsist) It's not the same Drew that Teardrops in my guitar is about though. Random I know but it's the only one I've seen of him in high school so even though it was taken two years before they dated it's closer to what he looked like then than pictures of him now are. Notice how he looks like the guy in the Tim McGraw music video, she did that on purpose! https://raretaylorswift.webs.com/apps/photos/photo?photoID=179652274 179652274 This is what Taylor's first boyfriend Drew looks like now. I'd post a picture of them together but I've never seen one. https://raretaylorswift.webs.com/apps/photos/photo?photoID=179652273 179652273 Taylor with her high school boyfriend Sam Armstrong who inspired her song Should've said no. https://raretaylorswift.webs.com/apps/photos/photo?photoID=152188626 152188626 Taylor with John Mayer when the first met at the 2009 Grammy's almost a year before they dated. https://raretaylorswift.webs.com/apps/photos/photo?photoID=176628549 176628549 https://raretaylorswift.webs.com/apps/photos/photo?photoID=202634876 202634876 https://raretaylorswift.webs.com/apps/photos/photo?photoID=202634886 202634886 https://raretaylorswift.webs.com/apps/photos/photo?photoID=203292743 203292743