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Clooney date Former MTV VJ Karen Duffy in 1995Hollywood playboy George Clooney who is famous for a string of relationships with gorgeous women, many of them actresses or models is now settling down with Amal Alamuddin .Alamuddin, 36, appears to be more accomplished and independent than many of Clooney’s former flames. She is not some waitress he picked up in Vegas or a wannabe actress. Alamuddin was already a well-known human rights lawyer before she hooked up with Clooney, 52.