3. Taylor Swift and John Mayer
Jake Gyllenhaal wasn’t the only older guy Swift has briefly dated. She was linked to John Mayer and opened up about the fling on her song “Dear John.” The relationship with John Mayer seems to be most bitter as Mayer recently admitted that he was “humiliated” by the song Swift wrote about him.
"It made me feel terrible," Mayer, 34, admitted in Rolling Stone’s June issue. "I didn't deserve it. 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."
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