Katy and Travis "Travie" McCoy began dating in 2006, at the beginning of her career. She and the Gym Class Heroes frontman hooked up after meeting at a recording studio, and she starred as his love interest in the band's video for "Cupid's Chokehold." He reportedly gave Katy a promise ring just before her debut hit, "I Kissed a Girl," was released in 2008, but the couple split a few months later. Travie revealed that Katy ended things with him via email (ouch) but blamed his drug use as the reason for their breakup. "She wasn't stupid. She knew when I was f*cked up," he said during a Behind the Music special in 2012. "I chose drugs over our relationship. As things started taking off for her, the more I started to doubt my role in her life. There were times I felt like a stepping ladder." Travie also partially inspired Katy's 2010 hit "Circle the Drain."
