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Their relationship was closely watched, and some thought Clooney had popped the question in 2010 when Canalis was photographed with a bauble on her finger.But it was actually a napkin ring she'd placed there as a joke.
Clooney won an Academy Award for Best Supporting Actor for the Middle East thriller Syriana (2005), and subsequently earned Best Actor nominations for the legal thriller Michael Clayton (2007) and the comedy-dramas Up in the Air (2009) and The Descendants (2011).
Before Alamuddin, the debonair actor had an illustrious dating history -- just take a look: Stacy Keibler: Clooney dated reality TV and WWE star Stacy Keibler from 2011 to 2013.
He was hesitant to discuss his romance with Keibler, as he told the Hollywood Reporter in 2012, "there is so little in my life that is private." News spread in July that the two had broken up for an undisclosed reason.
Today she's still married to Travolta and they're parents to Benjamin and Ella.
Even though Kelly took a break from acting after their older son Jett passed away, she is set to do two movies this year. Now we know her as Mona Sterling from Mad Men, where she plays opposite her real life hubby, John Slattery.