2005-2006 (Our Song, Tim McGraw, Fifteen)
Swift began dating Borello - then, a senior - her freshman year. They broke up the summer before he left for college, and she wrote Tim McGraw for him to remember her by. Taylor also penned Our Song about their relationship for a school talent show. Brandon is again referred to on Fifteen as the boy she swore she "would marry someday" until she "realized some bigger dreams." The lyrics lead us to believe he was presumably her first date, first kiss, and first real boyfriend. After the release of Taylor Swift, Brandon stated that he is happy Taylor remembers their relationship fondly.