The two were on friendly terms for years, working on various projects together. Swift had a cameo in 2009's Hannah Montana: The Movie
, and that same year, they sang Swift's song "Fifteen" at the GRAMMYs. The singers have gone very separate ways over the past six years, though both did date within the Kennedy family -- Swift dated Connor Kennedy in 2012, and Cyrus was with his cousin
, Arnold Schwarzenegger's son Patrick, in 2014.