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When: December 2009 — February 2010
Swift was romantically linked to Mayer when they collaborated on his song "Half of My Heart," but things between the couple quickly soured. Swift titled the breakup song "Dear John" about him, which clearly didn't hide who it was about. With lyrics like "Dear John, I see it all, now it was wrong / Don't you think 19 is too young to be played by your dark twisted games, when I loved you so?" the "Daughters" singer was none too pleased.
"It made me feel terrible, because I didn't deserve it," he told Rolling Stone in a 2012 interview. "I'm pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy thing for her to do."
Mayer found himself back in headlines with Swift in the weeks leading up to the release of "Speak Now (Taylor's Version)," as Lautner joked that he was "praying for John" — seemingly nodding to the re-release of "Dear John" and other "Speak Now" songs rumored to be about Mayer.