Inside Kelly Osbourne's Relationship With Her Famous Exes

Kelly Osbourne and musician Bert McCracken's relationship played out on television during the second season of Osbourne's family's show, "The Osbournes." The two certainly had a relationship that can best be described as on and off, and McCracken ultimately admitted to Playboy that he broke up with Osbourne in a pretty terrible way: over the phone. 

McCracken also said that, in the end, he wasn't ready to be in the type of relationship Osbourne wanted. But, as he told the publication, he was ultimately the problem. McCracken said, "She's the most important girlfriend I've ever had. We're best friends. It was always just so pleasant when she was around" (via Metro).

While speaking to MTV News in 2004, it was clear that despite those positive feelings, McCracken was also growing weary of being asked about his ex-girlfriend so often, especially as his band began to achieve success while the two were together. Despite that, in the end, it appears the two parted ways on friendly terms at the very least.