When Katy Perry achieved her breakout moment in 2008 with “I Kissed a Girl” and proceeded to embark on an unstoppable run of smash singles, the pop superstar also became a public figure, and her songs were tied to different romantic partners while her dating life was shoved into the spotlight. From her long-term relationship with Travie McCoy to her recent time spent with John Mayer to her latest rumored beau, we compiled a timeline of Perry’s high-profile (reported) former relationships, and matched a few of them to her music. A lot of these are based on clues and a few rumors, but we gave our best guesses — look and listen!