Sean Penn
Sean Penn was married to Robin Wright for 11 years when they separated and almost divorced–the couple withdrew the divorce petition in 2008. That same year, Penn, then 48, started dating model Petra Nemcova, then 28, while still married to Wright, then 43. After he and Wright split for good in 2010, he almost immediately took up with actress Scarlett Johansson, who was 26 at the time.
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