Sean Penn Girlfriends List (Dating History)

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Two-time Oscar winner Sean Penn always had a difficult relationship with Hollywood. He is loved and hated at the same time. However, Sean doesn't care what people think of him. Penn is not only a successful actor and director, but he is also a famous heartthrob. Here's what we know about Penn’s personal life.
Elizabeth McGovern
1983 – 1984
The first Hollywood girlfriend of Sean Penn was actress Elizabeth McGovern, his co-star in the melodrama Racing With the Moon. Their relationship did not last long.
Susan Sarandon
1984
When splitting from McGovern, Penn had a fleeting romance with actress Susan Sarandon.
Barbara Hershey
1984
Then, Sean reportedly had a brief affair with actress Barbara Hershey.
Madonna
1985 – 1989
When he met pop singer Madonna, Sean lost his head. In 1985, Penn and Madonna got married. Madonna dedicated her third album True Blue to Penn, calling him the coolest guy in the universe in her songs. But four years later their marriage fell apart. Numerous media sources stated that Penn was guilty of assaults on his wife. Madonna herself complained that her husband was beating her. So, in 1989, the couple got divorced.
Robin Wright
1990 – 2009
After Penn split from Madonna, he started his relationship with actress Robin Wright. The two welcomed two kids together before they went down the aisle in 1996. Their family life seemed to be ideal and the actor seemed to finally calm down his temper. But in 2010 everything ended with their divorce.
Elle Macpherson
1995
Penn was rumored to have a love affair with model Elle Macpherson when he was in his previous relationship.
Petra Nemcova
2008
Before his divorce was finalized, but after he announced his separation from his wife, the actor had a romance with Petra Nemcova.
Jessica White
2009 – 2010
Then, Penn was romantically linked with model Jessica White.
Scarlett Johansson
2011
Sean briefly dated actress Scarlett Johansson when he broke up with White.
Shannon Costello
2011 – 2013
During the next two years, Sean Penn had a relationship with film producer Shannon Costello.
Charlize Theron
2013 – 2015
Charlize and Sean had been close friends for about 18 years before they started dating. The actor was so much in love with the beauty that he was going to marry again and even called his feelings his first true love. He supposedly proposed to Theron and she said yes but their relationship ended in the summer of 2015. It happened presumably due to his infidelity.
Minka Kelly
2015
When the actor ended his relationship with Theron, he started dating Minka Kelly.
Leila George
2016
Then Sean met Leila George. In 2020, the actor confirmed that he tied the knot with his long-time girlfriend by proudly showing off his new gold wedding band. Leila is 27 years younger than Sean.
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00:00 - Sean Penn Girlfriends
00:21 - Elizabeth McGovern
00:35 - Susan Sarandon
00:42 - Barbara Hershey
00:49 - Madonna
01:19 - Robin Wright
01:40 - Elle Macpherson
01:48 - Petra Nemcova
01:59 - Jessica White
02:06 - Scarlett Johansson
02:13 - Shannon Costello
02:23 - Charlize Theron
02:48 - Minka Kelly
02:55 - Leila George