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Engaged: Six months
George Clooney left his bachelor days behind when he asked human rights lawyer Amal Alamuddin to marry him in April 2014 after just six months of dating. In September of the same year, they had a private ceremony in Venice, Italy, with guests like Matt Damon, John Krasinski, Emily Blunt, and Anna Wintour in attendance. The couple welcomed twins Ella and Alexander in June 2017.