This Oscar-winning actor got people asking and looking for his dating history when the news spread that he was now dating the youngest daughter of his actor colleague Vincent D’Onofrio. The two were seen spending time together and going on dinner dates several times. For good reasons, the “book” of Sean Penn’s dating history has not been supplemented since then, which is quite different from what celebrities usually do.
Let’s find out who Sean Penn dated, not only because he knows his ex-girlfriends (and boyfriends), but also because he had a long list of women he had an affair with since he became a public figure; this list will also mention women he allegedly dated or had an affair with.
Who Is Sean Penn Dating? Here’s A List Of His Ex-Boyfriends & Girlfriends
Sean Penn is not gay and as such is not known to have dated any man.
Sean Penn’s dating history with Stacey Nelkin began and remained a rumor. At best, the two had an affair with each other without there being more between them. Stacey is an actress who is famous for works like Manhattan and Halloween III.
Sean’s affair with Peggy Trentini puts an end to rumors about his affair with Stacey. According to reports, the two were romantically involved at the time before they decided to end their relationship. The reason for this is not yet known to us.
We learned about her romance with Sean Penn after she wrote about it in her autobiography. Brigitte is a Danish actress known for works like Red Sonja, Cobra, Rocky IV, Beverly Hills Cop II, and many others.
Between 1983 and 1984, Sean Penn met with Elizabeth McGovern. They both appeared on screen in the 1984 film Racing with the Moon. It is perhaps not wrong to assume that working together on the film project helped to connect their feelings for each other, but it is also not wrong to assume that what was between them was completely transitory, since Sean Penn was with two other women that same year.
After Elizabeth came Barbara, who took a place on the list of women Sean dated. Their 1984 relationship, like many others before it, did not last long as Sean moved on to another woman.
Susan was the last woman to be with Sean in 1984. It was never to be expected that their relationship would last long, as Sean is not associated with any relationship he enters into that is not long-lasting.
Madonna’s relationship with Sean Penn was not only as of the others, but the love between them was also so real that they wanted to marry. The two met in February 1985 and married on August 16, 1985, but unfortunately, they were no longer man and wife on September 14, 1989.
After his divorce from Madonna, he started with Jewel Kilcher in a relationship that lasted only a year before moving on to his next crush, where he gets her as fast as he wants.
Robin Wright Penn
With Robin, everything seemed right in Penn’s life. They met for the first time in August 1990, they were together for 6 years before they got married on April 27, 1996. Their relationship lasted 12 years before it broke up and finally succumbed to a sad divorce in July 2010. During the good times they were together, they had two children – Dylan Frances and Hopper Jack – who are now adults.
After his divorce, Sean Penn became the subject of celebrity gossip when he reportedly spent a night with Emily Llyod. Beyond that, nothing more was said about them, and it was best to leave it at that.
After his affair with Emily, Elle Macpherson came into the picture when the two began to meet in 1996. At first, it looked like they would continue the relationship, but nothing came of it.
Sean had a brief affair with Petra that began in January 2008 before they separated. Given the many relationships he has had in the past, most people were sure that his relationship with Petra Nemcova would not last, and yes, it did.
Between August 2009 and September 2010, Sean dated American model Jessica White, who is famous for Sports Illustrated’s Swimsuit Issue from 2003 – 2005, 2007, and 2008. Their relationship ended with each of them moving on with the new partners in their lives.
After White, he gave us reasons for concluding that Sean Penn’s dynamic dating list had been supplemented when he was spotted several times on dates with Valeria. It continued with a few more dates before they went their separate ways, or rather people stopped seeing them together and concluded that they were now separated.
Scarlett Johansson and Sean had a short date when it turned out that Sean Penn knew about women. Between February and June 2011 the couple was inseparable until what happens in all of Sean’s relationships happened again. We still do not know what it is that causes his frequent breakups.
The appointment between Garcelle Beauvais and Sean Penn was just a rumor like some others. However, for every rumor that exists, there may be an element of truth in it. The two were first seen on a dinner date in 2011, and everything else suspected in their relationship happened within the same year.
Sean was everywhere with Shannon Costello between July 2011 and 2013 and performed with her in various public places, as he had done on his other dates, but this was not his last one either.
In April 2012, the rumor circulated that Calu Rivero was involved with Sean Penn and had something going on with her until his next suitor called. Calu, like most of his other dates, is a savvy actress with several works to her credit.
Sean met Charlize Theron in December 2013 and became engaged to her for 7 months, which led to her 11-month engagement. It seemed as if they were going down the path of marriage, but by June 2015 it was all over.
There are a few records of Sean and Mina Kelly starting to meet since 2015, but it has not been confirmed whether this was a romantic relationship between the two or whether they were only acquainted with each other as they are both actors.
From the end of 2016 Sean Penn’s dating adventure with the daughter of actor Vincent D’Onofrio Leila George, who is also an actress, came to a standstill. The two made the headlines when they were spotted together on the beach and shared a deep kiss. There is an age difference of more than two decades between the two, and Sean Penn is also a year older than Leila’s father.