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11. Charlie Sheen and Brett Rossi

It’s hard to take any of Charlie Sheen’s recent relationships too seriously. The guy has to stop dating porn stars if he wants lasting love (don’t think he does). The notorious bad boy, age 49, proposed to the former adult film star, age 24, on February 14, 2014. However, he pulled the plug just weeks before their intended November wedding date. “I’ve decided that my children deserve my focus more than a relationship does right now,” Charlie explained. With three failed marriages and countless hookups behind him, it might be wise for this “winning” player to take a break from women for a while.

There are still a few days to go before the year ends. Do you think there will be any more celebrity splits of 2014?

famous people who actually turn 50
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