The reality star and Waits stepped out in late spring 2010, shortly after her final split from former "Hills" star Douglas Reinhardt. Explains the friend: "[Cy's] found it difficult to live his life with her in the spotlight and that's what caused their split. No drama, it's amicable, but things didn't work out."
Indeed, life as Hilton's beau was never low-key: Back in August, Waits was at Hilton's side when she was arrested for cocaine possession at a traffic stop in Las Vegas. The couple presented a united front this past April, when Waits accompanied Hilton as she testified against an alleged home intruder in an L.A. court. An overzealous fans threw water in Waits' faced and grabbed him by the neck before Hilton's security team intervened.