John Mayer: Dear John
Every list of Taylor’s songs about boys should begin with the one that actually names names. After a 2009 fling with John Mayer went wrong — he was 31, she was 19 — she infamously penned a song about his supposed betrayal, pointedly asking, “Don’t you think 19's too young to be played by your dark, twisted games?” Mayer, who allegedly brewed the bad blood between Taylor and Katy Perry by dating his ex’s BFF, told Rolling Stone the song “really humiliated” him. “"Because 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.”
Joe Jonas: Forever and Always
Who’s the unlucky guy who left Tay hanging on the other side of the phone call at the center of Forever and Always? That’s Joe Jonas, who dated Swift in 2008, before allegedly dumping her on a 28-second phone call for actress Camilla Belle. Swift’s ire didn’t just end with Jonas; she reserved her own barbs for Belle on the song Better Than Revenge, including the infamous line, “She's an actress, she's better known for the things that she does on the mattress.”
Jake Gyllenhaal: We Are Never Getting Back Together — and, well, most of Red
Some of Tay’s exes were bad enough to inspire a handful of songs. Gyllenhaal dissed her so hard, she wrote a near-entire album about the breakup. The hallmark of Swift’s angstyRed was We Are Never Getting Back Together, where she mocked an unnamed guy with “And you, would hide away and find your peace of mind / With some indie record that's much cooler than mine.”
Harry Styles: I Knew You Were Trouble
One song — well, at least one we know of — off Red is about a different mop-haired brunette who’s nothing but trouble. One of Tay’s finest breakup songs — and best songs, period — is her EDM-flirting I Knew You Were Trouble, which was allegedly inspired by her fling with the One Direction heartthrob. She hinted at the song’s source material in an interview about performing Trouble at the BRIT Awards in 2013, where the 1D boys were in attendance. "It's not hard to access that emotion when the person the song is directed at is standing by the side of the stage watching," she said.
Katy Perry: Bad Blood
One of Taylor’s most stinging indictments deviates from her traditional diss-track pattern — it’s only tangentially about a guy, channeled through her anger at a friend’s betrayal. Or, at least that’s what fans surmised when the song appeared on 1989, appearing to reference Taylor’s Mayer-fueled fallout with Katy Perry. This week’s drama only confirms this theory, after Perry cheekily responded to Harris’ tweet about how he wouldn’t let Taylor “bury” him like she tried to do with her former friend.