George Clooney: His Lady Loves

Meet the women who were unable to tame Hollywood's most eligible bachelor – until now


Dated from 2007-2008
Clooney initially met the cocktail waitress at his birthday bash, where they "were dancing, taking pictures, being silly," Larson recalled of her first meeting with the A-lister before they became an item years later. The couple attended the Oscars together (pictured here) – a first for the actor, who had never taken a girlfriend to the Academy Awards – but broke up shortly afterward in May 2008.