They say, "once bitten, twice shy," and this seemed like it would always be the case for superstar George Clooney, who vowed to never remarry after his 1993 divorce from actress Talia Balsam. Clooney became a perpetual bachelor, often in the news with a new beauty on his arm.
However, it seems things have changed. News broke on Saturday, April 26, that George popped the question again, asking his 30-something girlfriend Amal Alamuddin to marry him. The couple has only been dating since October of last year, and things seem to be moving pretty fast for the lovely duo. But what about the 50-something Oscar winner's past relationships, some of which lasted quite a while without taking that next step toward engagement?
Here's a look back at Clooney's longest relationships.