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Everyone has their addiction, and Oscar winner Sean Penn has the most interesting of all. He can’t live without beautiful women – preferably popular and named “the sexiest women” in the world.

During his rich career, Penn also had a vibrant love life, and he dated many famous beauties, from Madonna to Scarlett Johansson. But let’s go in order.

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He was engaged to colleague Elizabeth McGovern in 1984, but she ended the relationship. It didn’t take him long to cast an eye on the next familiar face, and this time he chose the queen of pop. Madonna and Sean Penn were married from 1985 to 1989 but did not end happily.

The actor ended up in prison at the time for insane driving and was followed by rumors of alleged domestic violence. Still, that didn’t stop him from continuing to make love to beauties after Madonna.

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He was allegedly in a relationship with the singer Jewel for a while, in 1995. He also directed her music video for the song “Were Meant For Me”. Penn moved to actress Robin Wright in the 1990s, and they got married in 1996. They had numerous problems in their marriage and parted and reconciled several times. After multiple attempts to save the relationship, they divorced in 2010.

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Penn did not rest other beauties even during the breaks in his relationship with Robin. He was briefly in a relationship with supermodel and activist Petra Nemcova in 2008, and the romance was renewed four years later. He sought solace after the divorce from Robin Wright in the embrace of model Jessica White. They were together for a short period.

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In 2009, the paparazzi also caught him in the arms of Natalie Portman. They were kissing at the Sunset Towers Hotel in Los Angeles, but when a passerby spotted them, they pretended nothing had happened. Age has never been a problem for him, especially when it comes to handsome actresses. After divorcing Ryan Reynolds, Scarlett Johansson found solace in a 24 years old colleague. They didn’t last long, but enough to mention them.

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After Scarlett, Sean switched to Shannon Costello, a 26-year-old PR expert. The love of his life was also Charlize Theron. Although they told everyone how much they were in love, Theron broke off their engagement in 2015 after a two-year relationship. Years later, Charlize pointed out that there was nothing sensationalistic about their breakup. Although the media claimed that at one point she just stopped calling him, the actress dismissed the rumors and said that the relationship simply failed due to numerous disagreements.

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