Dated from 2009-2011 The Italian actress enjoyed life in the limelight with the two-time Sexiest Man Alive, taking strolls down the Academy Awards red carpet and jetting to Hawaii. "I love it," Canalis told PEOPLE of her romance with the Oscar winner. But two years after they first stepped out together as a couple at the Venice Film Festival, Clooney and Canalis announced the end of their romance on June 22. "We are not together anymore," they said in a joint statement. "It's very difficult and very personal, and we hope everyone can respect our privacy."