7. Sean Penn and Charlize Theron
Another celebrity with a somewhat bad reputation is Sean Penn. Despite his activist duties and his high-profile film roles, lots of people choose to focus on his tendency to abuse alcohol and womanize. He also has a mean streak. Once upon a time, he was married to pop goddess Madonna (whom he allegedly physically abused), and then he moved on to Robin Wright, another actor. The couple had two children together and eventually married in 1996, nearly divorced in 2007, got back together not too long after, and then finally divorced for real in 2010.
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For a few years, Penn focused on his activism and his movies, getting with Scarlett Johansson in a blink-and-you’ll-miss-it moment in 2011 but otherwise remaining single. That all changed towards the end of 2013, when he and Charlize Theron started seeing each other romantically. Although seemingly mismatched, the two were terribly happy together. A year after they first started dating, Penn got down on one knee for the third time in his life and Theron accepted. For a while, we believed that these two long-term friends were going to last. However, Theron, for reasons known only to her, dumped Penn earlier this summer.
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