Mayer shocked many with his next high profile relationship. In 2009, he began dating fellow singer-songwriter Taylor Swift. She was 19 years old at the time, while he was 32 (per Evening Standard). Swift wasn't shy about the fact that the breakup was not amicable. In her song "Dear John," she wrote, "Don't you think 19 is too young to be played by your dark twisted games, when I loved you so?" (per Genius).
That was far from Mayer's last famous fling, however. After Swift, he was linked to Miley Cyrus, Kim Kardashian, and Reena Hammer (per More). There was one more famous songstress in his sites, however. In 2012, rumors began circulating that Mayer was seeing Katy Perry, fresh off her divorce from Russell Brand. Mayer and Perry waited some time to confirm that they were an item. She discussed it when talking about the track "Legendary Lovers" off her album Prism.
"I actually wrote it in an email one time, and after I wrote it I looked — we had a long courtship before anything was [public], just writing letters to each other — and seeing 'legendary lovers,' it sounded so nice," she told Entertainment Weekly. "Some things float into my mind, and I process them, and [then] I make songs about them."
