(Dated Summer 2007-December 2008)
When Perry first broke big with "I Kissed a Girl," she was busy kissing Travie McCoy, the frontman of Gym Class Heroes who later scored a solo hit with "Billionaire." The on-and-off relationship ended at the end of 2008, when McCoy posted on his blog confirming the split on New Year's Eve. "Circle The Drain," from Perry's blockbuster 2010 album "Teenage Dream," reportedly touches upon her first stint as part of a power couple.
Perry dated Gym Class Heroes frontman Travis McCoy, whom she met in a recording studio in New York, on and off for several years. After more than a year of friendship and casual dating, they became serious with their relationship right before they embarked into the 2008 Warped Tour. Perry and McCoy broke up in December 2008 but got back together for a few weeks in 2009.