Who: 12-time Grammy-winning singer and songwriter Taylor Swift, 33, and seven-time Grammy-winning singer, songwriter, and guitarist John Mayer, 45.
How They Met: Back in March 2009, Mayer and Swift first connected on social media after the “Your Body Is a Wonderland” singer tweeted that he wanted to collaborate with the 19-year-old country-pop star.
At the time, he tweeted that he had an idea for a song “called ‘Half of My Heart,’” adding, “I want to sing it with Taylor Swift. She would make a killer [Stevie] ‘Nicks’ in contrast to my [Tom] ‘Petty’ of a song.” Swift was giddy over Mayer’s Twitter mention and told Elle: “I freaked out when I heard, because I’ve been such a big fan of John for such a long time. I’m really excited about just the idea that he would even mention me in his Twitter!”
Eight months later, the duo released “Half of My Heart” on John’s Battle Studies album — and while they weren’t a couple just yet, Mayer still couldn’t help but gush about Swift during his press tour.
Taylor is the world’s biggest star who doesn’t know she’s a star … which I think is totally sweet,” he told Access Hollywood. “It’s almost like Taylor Swift is a character in a movie about a small-town girl who has her dreams come true and [does] what any small-town girl would do when her dreams come true, which is to freak out. And I still like it that she freaks out, but pretty soon she’s gonna have to stop because it’s sort of like, ‘You’re that good. You’re that good. You might have to go to therapy and have someone else tell you.'” He also called her “one of the smartest, most talented people around” during an appearance on The Ellen DeGenres Show.
Fresh off her breakup from Taylor Lautner in December 2009, Swift and Mayer performed “Half Of My Heart” at the Z100 Jingle Ball. Their chemistry was so palpable onstage, people instantly presumed the two were dating and it appeared as if they were right — a month later, John and Taylor were spotted grabbing dinner together in Nashville, and, again, at the the taping of CMT’s Crossroads, where John performed with Keith Urban and Taylor danced and sang along in support in the audience.
Why We Loved Them: Their romance may have been brief, but it has captured the internet’s attention with drama that has carried on for more than a decade (and counting).