Sean Penn, 53, is no stranger to high-profile romances. The 50-year-old Oscar-winner was once upon a time engaged to pop queen Madonna. The celebrity couple tied the knot in 1985 and their marriage was wrought with violence, mostly due to Penn’s wild temper. In 1986, he attacked musician David Wolinski for hitting on his famous wife in a nightclub, for which he was charged $1,000 and slammed with a year-long probation period.

Then, after spending a month in jail for assaulting a man trying to snap a picture of him, Sean Penn was charged with felony domestic assault against Madonna. The celebrity couple finally ended their marriage and their divorce was finalized in 1989.

Shortly after his divorce, Sean Penn started dating actress Robin Wright. After having two kids together, the celebrity couple tied the knot in April 1996, but their marriage was tumultuous, to say the least. They filed for divorce in December 2007, but then requested it to be dismissed, as they had seemingly worked out their differences. Less than a year later, Penn filed for a legal separation, but then withdrew it the next month. In August 2009, the celebrity couple filed for another divorce, and this time, it would be final.


After the demise of his second marriage, Sean Penn was linked to a number of much younger women, including 29-year-old model Jessica White, 29-year-old A-list actress Scarlett Johansson, 27-year-old producer Shannon Costello, and 26-year-old Spanish model and actress Calu Rivero. But none of these May-December relationships seemed to be quite as serious as his latest one: 38-year-old Oscar-winning actress Charlize Theron.

The celebrity couple was first rumored to be dating back in 2010, because they were seen spending a lot of time together. The rumors were eventually dismissed, but they resurfaced when Penn and Theron rang in 2014 together in Hawaii. After returning to L.A., they spent the next few days together. Although neither of them confirmed directly that they were dating, the celebrity couple made it pretty clear they were an item when they showed up together at one of Penn’s charity galas.

The celebrity couple has since been inseparable. Penn has been seen spending quality time with Theron’s two-year-old adopted son. Rumor has it their May-December relationship is getting so serious that they’re actually considering marriage.

What do you think: Do Sean Penn and Charlize Theron make a good couple?

Photo Credit: Jaguar PS / (Sean Penn), Featureflash / (Charlize Theron)


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